Workshops and Masterclasses

Real experts share their insights and recommendations. Rewatch some of our top webinar events and learn best practice tips, covering all aspects of short-term rentals.

Type

Upcoming

(3)

Recurring

(1)

Past

(66)

UPCOMING EVENTS

Stop Answering the Same Guest Questions Every Day

If you’re constantly typing the same replies, you’re working harder than you need to. Hospitable’s messaging tools automate the daily conversations you have with guests—without making your messages feel robotic. In this workshop, we’ll show you how to build a messaging workflow using message templates, Smart Conditions, Custom Codes, and Message Preview so every guest receives the right information at the right time. You’ll also learn common messaging mistakes that lead to unnecessary guest questions and how to avoid them.

What You'll Learn

✅ Build message templates that automatically personalize every conversation

✅ Use Smart Conditions to send the right message at the right time

✅ Save time with Custom Codes instead of manually updating messages

✅ Preview your guest journey before messages go live

✅ Create a messaging workflow that reduces repetitive questions and saves hours each week

By the end of the session, you’ll have a messaging system that saves time while delivering a consistent guest experience from booking through checkout.

Managing Your Owners, Statements, Invoices, and Payouts

Still spending hours pulling together spreadsheets, taking screenshots, and answering the same owner questions every month? There's a much easier (and far more professional) way.

Whether you've just signed your first co-hosting client or you're managing a growing portfolio of vacation rentals, keeping owners informed is one of the most important—and time-consuming—parts of the job. The good news? It doesn't have to be.

In this workshop, we'll show you how to simplify owner management with automated statements, professional invoices, clear payout tracking, and reports your owners will actually love receiving. Instead of piecing together information from multiple tools, you'll learn how to create polished financial reports in just a few clicks.

We'll cover:

📊 Creating beautiful owner statements in minutes
💸 Managing payouts without the spreadsheet headache
🧾 Generating invoices for management fees and additional charges
📈 Giving owners the transparency they want while saving yourself hours every month
🤝 Tips for delivering a premium owner experience that helps you retain clients and grow your business

If you've ever thought, "There has to be a better way," this workshop is for you.

Join us and discover how to spend less time building reports and more time growing your portfolio. Your owners will appreciate the professionalism—and you'll appreciate getting your evenings back.

The 15-Minute Setup That Can Save You Thousands

No one starts hosting expecting a guest to throw a party, damage the property, or ignore the house rules... but every experienced host knows that sometimes, things happen.

The good news? One of the best ways to protect your business takes about 15 minutes to set up.

In this workshop, we'll show you how to use Hospitable's Rental Agreement feature to collect legally binding electronic signatures before guests arrive, helping set clear expectations from the moment a reservation is confirmed. We'll also explore guest verification options available through Hospitable, when they make sense, and how they can add another layer of confidence for your bookings.

We'll cover:

📝 Creating and customizing your rental agreement
✍️ Automatically collecting electronic signatures before check-in
🛡️ Understanding guest verification and when to use it
⚖️ Reducing risk while setting clear expectations with every guest
⚡ Setting everything up in about 15 minutes

Whether you're managing one property or one hundred, having the right protections in place can save you from costly headaches down the road. Think of it as insurance for your sanity—with a much faster setup.

Join us and learn how a few minutes of preparation today could save you thousands tomorrow, while giving you greater peace of mind every time a new reservation comes in.

RECURRING EVENTS

Getting Started with Hospitable

Get up and running with Hospitable faster and learn the key workflows that successful hosts use every day.

In this live session, our team will walk you through the essentials of getting started with Hospitable, from connecting your booking channels to setting up automations that save time and improve the guest experience.

Whether you're exploring Hospitable during your trial or you've recently signed up, this session will help you build a strong foundation and start seeing value sooner.

You'll learn how to:

Get your account set up
Connect your booking channels and review key settings
Automate guest communication and operational workflows
Avoid common setup mistakes
Make the most of Hospitable's tools, resources, and support

You'll also have the opportunity to ask questions and learn alongside other hosts who are getting started with Hospitable.

Reserve your spot today and start hosting with confidence. 💜

This session is currently being offered weekly on Tuesdays.

PAST EVENTS

The STR Revenue Audit: Find the Gaps Costing You Money

In this live workshop, we'll walk through a complete revenue audit framework used by successful short-term rental operators to uncover hidden opportunities across every part of their business.

You'll learn how to identify where money is being left on the table, reduce unnecessary workload, and build systems that help your business grow more efficiently.

What You'll Learn:

✅ How to identify pricing gaps that could be costing you bookings or reducing revenue

✅ Where direct booking opportunities are hiding - and simple ways to capture more commission-free reservations

✅ The biggest automation opportunities that save hours every week while improving the guest experience

✅ Common operational bottlenecks that slow your business down as you grow

✅ Which Hospitable features are most commonly underutilized - and how to get the most value from them

✅ A simple framework for prioritizing improvements that deliver the biggest ROI first

Whether you manage one property or an entire portfolio, you'll leave with a practical checklist you can immediately apply to improve revenue, increase efficiency, and get more value from your software stack.

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Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

Hospitable is the short-term rental industry's premier super app, empowering hosts and property managers to streamline operations, grow their businesses, and reclaim valuable time. Initially launched in 2016 as a time-saving PMS, Hospitable has evolved into a powerful toolkit that goes beyond traditional property management.

The platform enables hosts at every scale to automate guest messaging with AI, optimize nightly rates, simplify rental agreements and deposits, coordinate teams, and confidently launch direct booking websites with built-in payments and property protection. Hospitable supports tens of thousands of hosts worldwide, having automated over 108 million messages and processed $5.2 billion in reservation income in 2025.

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The Growth Blueprint for STR Operators

The hosts who successfully grow to 5, 10, 20, or even 50+ properties aren't working harder than everyone else. They've built systems that allow their business to scale without creating chaos.

In this live workshop, we break down the operational playbook used by successful property managers and professional hosts to create a business that runs smoothly, delivers an exceptional guest experience, and continues growing without requiring them to be available 24/7.

Whether you're managing a single property today or actively growing your portfolio, you'll learn how to build the foundation that supports long-term growth.

What You'll Learn:

✅ The operational systems every growing host should have in place before adding more properties;

✅ How to layer automations together to eliminate repetitive work and reduce human error;

✅ Team workflows that keep cleaners, co-hosts, virtual assistants, and staff aligned;

✅ How to manage property owners professionally and create a better ownership experience;

✅ Communication systems that scale across multiple properties without sacrificing guest satisfaction;

✅ The technology stack professional operators use to streamline operations and improve efficiency;

✅ Common growth mistakes that create bottlenecks and how to avoid them;

✅ How to spend less time putting out fires and more time focusing on revenue and growth.

Who Should Attend?

- Hosts managing 1-10 properties who want to grow
- Property managers looking to improve operations
- Hosts considering hiring help or building a team
- Anyone feeling overwhelmed by day-to-day management
- Professional operators looking to improve efficiency and profitability

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Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

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5 Ways Hosts Are Leaving Money on the Table

Most hosts think they need more properties to make more money. Usually, they just need to better optimize the ones they already have.

In this free workshop, we walk through practical ways hosts are increasing revenue using tools already available inside Hospitable.

We’ll cover:

- smarter pricing strategies;
- reducing OTA fees with direct bookings;
- easy upsells guests actually buy;
- automation workflows that save time;
- operational improvements that help hosts scale.

Whether you manage 1 property or 100, you’ll leave with actionable ideas you can implement immediately.

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Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

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Stop Guessing Your Rates: Smarter Pricing for More Revenue

Still setting your nightly rates based on gut feeling, nearby listings, or what “feels right”? You could be leaving serious money on the table.

In this live masterclass, we’ll break down how top-performing hosts use dynamic pricing strategies to increase revenue, improve occupancy, and stay competitive without constantly adjusting rates manually.

We’ll cover:

- The biggest pricing mistakes hosts make;
- How to optimize for weekends, events, and high-demand dates;
- Finding the right balance between occupancy and ADR;
- Minimum stay strategies that actually work;
- How to price during slow seasons without tanking your calendar.

You’ll also see how Hospitable Dynamic Pricing can help automate smarter decisions using real market data, demand trends, and booking behavior.

Whether you manage 1 property or 20+, this session will give you practical strategies you can start using immediately to make more from every booking.

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Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

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The Lazy Host's Guide to Better Operations

What if you could spend less time managing your rentals and still deliver a better guest experience?

In this workshop, we show you how successful hosts use automation, AI, and smart devices to eliminate repetitive work, reduce operational headaches, and free up hours every week. Whether you manage one property or a growing portfolio, the right systems can help you do more with less effort.

You'll learn:

- How to automate guest communication with Inbox AI;
- Smart lock workflows that simplify check-ins and improve security;
- Ways to reduce repetitive tasks and manual follow-up;
- Automated review strategies that help generate more guest feedback;
- How to create a more scalable operation without adding more work;
- Practical automation ideas you can implement immediately.

By the end of the session, you'll have a clear roadmap for saving time, reducing stress, and building a more efficient vacation rental business.

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Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

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https://twitter.com/hospitable

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Repeat Guest Machine: Turn Past Guests Into Future Bookings

You don't need a huge marketing budget, a professional advertising agency, or a complex website to start generating more direct bookings.

In this workshop, we break down the practical strategies successful hosts use to build direct booking channels that consistently bring guests back year after year.

You'll learn how to capture guest information throughout the guest journey, build a valuable guest database, and create simple marketing systems that keep your property top of mind long after checkout. We'll also cover easy ways to drive traffic from social media, encourage repeat stays, and reduce your dependence on third-party booking platforms.

Whether you manage one property or a growing portfolio, these strategies can help you increase revenue, strengthen guest relationships, and build a more resilient vacation rental business.

What you'll learn:
✅ How to build a repeat guest marketing system that generates future bookings;
✅ Simple QR code and email capture strategies that grow your guest database;
✅ Ways to turn website visitors and social media followers into future guests;
✅ How to stay connected with past guests through email marketing;
✅ Strategies to reduce OTA dependency while maintaining occupancy;
✅ The key components every direct booking website should have;
✅ Common mistakes hosts make when trying to generate direct bookings;
✅ Quick wins you can implement immediately after the workshop.

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Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

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The Hidden Revenue Playbook: Make More From Every Guest

The most successful vacation rental operators know that maximizing revenue doesn't stop when a guest books. Small, well-timed offers can create a better guest experience while generating meaningful additional income from every stay.

In this workshop, we show you how to unlock new revenue opportunities using Hospitable's Upsells feature and proven strategies used by high-performing hosts.

You'll learn:

• How to offer early check-in and late checkout without creating operational headaches

• When and how to charge pet fees that guests are happy to pay

• Ways to partner with local businesses to create additional revenue streams

• Experience add-ons that increase guest satisfaction and spending

• The ideal timing for upsell offers to maximize conversion rates

• Common mistakes hosts make when presenting upsells to guests

• How to create upsell workflows that feel helpful rather than salesy

• Real-world examples of hosts generating more revenue from existing bookings

Whether you manage one property or an entire portfolio, these strategies can help you increase revenue, improve guest experiences, and get more value from every reservation that comes through your calendar.

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Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

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https://www.linkedin.com/company/hospitable/
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https://twitter.com/hospitable

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Maximize Your Vrbo Performance with Hospitable

Following the highly anticipated launch of Hospitable's Vrbo Partner Connection, this workshop is dedicated to helping you unlock the full power of this integration.

We walk you through how to seamlessly launch, migrate, and manage your Vrbo listings using Hospitable. We are joined by Lee Maz, Senior Business Development Manager, North America, PM Acquisitions at Vrbo.

This workshop covers:

- Why list on Vrbo;
- Why use Hospitable to manage Vrbo;
- How to get started with Vrbo from Hospitable;
- How to switch across to the new connection if you're already on there;
- Tips for optimizing Vrbo.

Whether you manage 1 property or 100, you’ll leave with the exact technical blueprint to get connected and optimized immediately.

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Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

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Designing AI systems with Hospitable MCP

Ready to go beyond individual workflows? This session shows you how to design AI systems that can handle more complex, multi-step operations across your hosting business.

We’ll build on the workflows from the previous session and explore how to connect them into more powerful, scalable setups.

Here’s what we’ll cover:

- Moving from single workflows to systems:
- Multi-step automations
- Agent-style workflows and decision logic
- How context flows between steps and tools
- How to design scalable AI processes
- Advanced use cases across tools and functions

You’ll leave with the ability to design, extend, and adapt your own AI systems using MCP.

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Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

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Customer Support Workshop

Meet Smarty, Hospitable’s AI-powered support tool designed to help you find answers faster and solve issues independently. In this workshop, we’ll show you how to get the most out of Smarty - sharing practical tips to improve your prompts, uncover solutions you might not expect, and save time in your day-to-day operations.

And while Smarty is more powerful than you think, you’ll also learn how and when to seamlessly escalate to human support on Legacy, Host, Professional, and Mogul plans if needed.

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Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

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Hospitable MCP in Practice

Ready to go beyond the basics? This session shows you how to use MCP to run workflows you can copy, adapt, and put into practice right away.

Building on the intro session, we’ll focus on simple setups that work for everyday hosting and don’t require a technical background.

Here’s what we’ll cover:
- Proven workflow patterns you can reuse across your listings
- Simple prompt “recipes” to guide how AI responds
- What can go wrong, and how to avoid it
- A live build of one complete workflow you can copy and adapt.

You’ll leave knowing how to set up at least one practical workflow and how to build on it as you go.

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Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

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Hospitable MCP: What it is (and why hosts should care)

Curious how AI can actually help with your day-to-day hosting tasks? This session will show you where to start, even if you’re completely new.

We introduce MCP in simple terms and walk through how it connects AI to the tools you already use, so you can save time and reduce manual work.

Here’s what you’ll learn:

- What MCP is, explained in plain language;
- Where AI fits into your hosting workflow (no technical background needed);
- Practical use cases you can relate to;
- What you need to get started, including tools, data, and access;
- A live demo of a simple automation you can try yourself.

Whether you’re just getting started with AI or already experimenting, you’ll leave with a clear understanding of how this can fit into your hosting business.

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Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

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https://www.linkedin.com/company/hospitable/
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https://twitter.com/hospitable

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The Global Football Travel Boom: A Host’s Guide to 2026

Derek Jones (VP of Sales & Partnerships at Hospitable) and Annie Holcombe held a practical workshop on how hosts can prepare their properties and listings for a major global sporting event.

We covered how international travel patterns differ from typical bookings, what amenities global travelers expect, and how to optimize your listing and pricing strategy to capture longer stays and high-value reservations.

During this session, you’ll learn how to:

• Understand which cities will see the highest demand

• Identify the types of guests attending major international sporting events

• Use dynamic pricing, minimum night strategies, and event-based rules to maximize revenue without blocking longer bookings

• Prepare your property with amenities international guests expect

• Update your listing to highlight proximity to stadiums and public transportation

• Expand distribution across channels like Booking.com

• Create a direct booking website and improve visibility on Google

• Use AI-powered messaging translation to communicate with international guests

• Offer thoughtful upsells and add-ons that enhance the guest experience

Whether you’re located in a host city or nearby travel hub, this workshop will help you prepare your short-term rental for one of the biggest global travel moments of the decade.

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Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

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Power-Up Workshop: Operations

This Power-Up Workshop focuses on Hospitable Tasks, where we show you how to unlock the full potential of Hospitable's latest features for cleaner management and payment automation.

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Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

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Staying Compliant All Year with Hospitable

Understanding taxes is one thing. Managing them consistently throughout the year is another.

In this final session (3/3), we focus on how US-based short-term rental hosts can approach reporting and compliance as an ongoing process, and how different hosting setups influence what’s required.

We covered:

- How tax and reporting responsibilities differ across Hospitable plans, including Direct Basic and Direct Premium;
- What it means for Hospitable to be the merchant of record, and how that affects tax handling;
- What hosts can generally expect from tax reporting, including concepts like 1099-Ks and annual earnings summaries;
- How Hospitable supports reporting and record keeping, including integrations with tools like QuickBooks Online;
- Considerations for hosts operating as owners, arbitrage operators, or property managers.

This session brings the series together by connecting earlier concepts with day-to-day workflows and reporting practices.

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Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

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https://twitter.com/hospitable

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STR Taxes 101 (US): Income, Expenses, and Depreciation

This second tax session focuses on the practical mechanics of STR taxes. We took a closer look at how income and expenses are typically treated for US-based short-term rental hosts, how reporting works in practice, and what hosts should be tracking throughout the year to stay organized and prepared.

We've covered:

- What is generally considered STR income, including accommodations, fees, pay-through taxes, and more;
- How gross income is reported when booking through OTAs, versus net payouts after platform fees;
- Common expense categories and timing considerations, including reimbursements and future reservations;
- Accounting methods at a high level, including cash versus accrual (and how taxes are typically handled);
- Practical approaches to tracking income and expenses during the year;
- How tax considerations can differ for owners, arbitrage operators, and property managers.
We’ve also set the stage for the final session, where we’ll look more closely at how reporting and compliance are handled in practice, including how Hospitable fits into different hosting setups.

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Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

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https://www.linkedin.com/company/hospitable/
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https://twitter.com/hospitable

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How to Add Booking.com Without Adding Risky Guests - Hospitable Conference

Expand your reach with Booking.com—without sacrificing host control or property protection.

In this Hospitable Online Conference session, Emily (Booking.com) and Derek (Hospitable) break down the newest tools designed to help short-term rental hosts attract more global travelers while staying secure: Request to Book screening, stronger guest insights, built-in insurance coverage, and safer payments—plus how the Booking.com ↔ Hospitable integration helps prevent double bookings and keeps your pricing in sync.

What you’ll learn:
• Booking.com’s “Insights, Control, Coverage” framework for worry-free hosting
• Request to Book: how to message + vet guests before accepting
• Guest profiles, verified essentials, and identity verification pilots
• Built-in protections: liability insurance + host property insurance (where available)
• Payments by Booking.com: fraud/chargeback support, daily payouts, and global payment methods
• Cybersecurity updates + host best practices (2FA, account hygiene, safe messaging)
• Q&A: request-to-book eligibility, traveler types, invoices/commission timing, cancellations, promos, and more

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Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

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Is MTR Right for You? Market Analysis & First Steps Made Simple - Hospitable Conference

STR regulations tightening in your market? Looking for more stability without going fully long-term? In this session, Jesse Vasquez breaks down the mid-term rental (MTR) model and helps you decide if it’s the right fit for your portfolio.

Jesse explains what makes an MTR market work, how to identify demand drivers (healthcare, insurance housing, infrastructure projects, corporate travel), and how to think beyond platforms by building direct relationships with companies that need housing.

In this session, you’ll learn:
• What “mid-term rental” actually means (and who it’s best for)
• How to evaluate your market for MTR demand
• The biggest MTR demand drivers: hospitals, insurance, construction, military, universities, and more
• Why smaller markets can be better than big cities for stable MTR occupancy
• How to use MTR as a strategy to reduce STR regulatory risk
• How to pitch yourself as a “housing solutions provider” to local businesses

Jesse also covers:
✅ The STR + MTR hybrid strategy (seasonal approach)
✅ How to spot local projects bringing in traveling workers
✅ Why relationships can outperform “list and wait” marketing
✅ How to think like an operator—not just a landlord

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Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

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How to Improve Your Listing in 15 Minutes - Hospitable Conference

Your listing is the lifeblood of your STR business—and in today’s competitive market, small changes can unlock big booking gains. In this session, Chris Kennedy (Hospitable Sales + STR host) shows you how to make quick listing improvements that help you rank higher, get more clicks, and convert more guests.

This is designed to be actionable: pull up your listing and make at least ONE change today.

What you’ll learn:
• Why listing optimization matters more than ever (competition + algorithm pressure)
• How to view your listing through the guest booking journey:
1. Rank higher in search
2. Earn the click
3. Convert the booking
• How to define your Ideal Guest Profile (based on reviews + booking patterns)
• The top listing wins you can implement fast:
• Better hero photo + top 5 photo sequence
• Photo captions (often overlooked—can help performance)
• Stronger listing headline (avoid duplicating city/bed count)
• Improvements to About this space (clear, scannable, bulleted)
• Expanding and aligning amenities (Airbnb adds new ones often)
• Pet-friendly positioning (and how to “sell” it properly)
• Host profile upgrades (trust + conversion boost)
• How Superhost + Guest Favorite badges impact credibility and ranking

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Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

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More Places, More Bookings: Building Your Visibility Strategy - Hospitable Conference

OTAs aren’t the enemy—but over-dependence is risky. In this session, Annie Holcombe and Alex Husner unpack what a smart distribution strategy really looks like in 2026: how to balance OTAs, diversify channel mix, and build a direct booking engine that supports long-term growth.

They also dig into channel differences (Airbnb vs. Vrbo vs. Booking.com vs. niche channels), why direct wins key KPIs, and practical steps you can take right now to drive more repeat and direct guests—without trying to “outspend” OTAs.

In this session, you’ll learn:
• Why distribution is more complex than ever (10,000+ channels + shared inventory)
• How to match channels to your market + guest types
• Why direct tends to win on ADR, length of stay, and booking lead time
• What “healthy” channel mix can look like (and what’s too risky)
• Direct booking fundamentals that actually convert (especially on mobile)

Topics covered include:
✅ Channel strategy by guest type (families, last-minute, business, loyalty travelers)
✅ Booking.com for international travel (World Cup readiness)
✅ How to pressure-test your website booking flow (including the “grandma test”)
✅ Branding everywhere (website, listing profiles, inside your property)
✅ Guest journey + messaging audit so you don’t overwhelm guests with emails

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Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

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Upsells: What Items Sell and the Psychology Needed to Get Guests to Spend - Hospitable Conference

Upsells aren’t just “extra charges”—done right, they’re delightful experiences that guests didn’t expect… and instantly value. In this session, Chris Kennedy breaks down what upsells actually sell, why guests love them, and how to set them up in Hospitable so they’re automated and easy to buy.

You’ll learn:
• The upsell mindset shift: from “add-ons” to delight + convenience
• What guests expect for free (and what not to upsell)
• Upsell ideas that work (products + services), including:
• Early check-in / late checkout
• Welcome baskets, snacks, movie kits
• Birthday/anniversary decorations
• Baby gear, pet welcome kits
• Firewood/s’mores kits
• Pool heat, mid-stay cleans, private chef, rentals/transfers
• Trip insurance (new, automated, and commission-based in eligible markets)
• The revenue potential (from small monthly wins to top performers)
• How to pitch upsells so they feel helpful—not salesy

Live walkthrough: How to set up upsells in Hospitable
Chris shows how to:
• Create upsells in the platform (pricing, photos, descriptions)
• Control when they appear (timing windows)
• Use guest portal links in automated messages
• Automate early check-in / late checkout using custom codes
• What guests see in the Guest Portal and how they purchase

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

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Cash Flow + Tax Flow: The Dual Strategy That Supercharges Your STR Wealth - Hospitable Conference

If you’re focused on cash flow but ignoring tax strategy, you might be leaving tens (or hundreds) of thousands on the table. In this session, Michael Elefante shares how STR investors can maximize cash flow and unlock major tax advantages—including how the short-term rental tax strategy can potentially offset active income (depending on your situation).

Michael walks through market selection, competitive advantage, “Monopoly-style” property positioning, and the fundamentals behind depreciation + cost segregation—with real-world examples from his portfolio.

In this session, you’ll learn:
• How to pick markets with durable demand (tourism + population growth)
• How to build a “buy box” that helps you avoid average listings
• Why “one-of-one” properties win (features that are hard to replicate)
• Cash flow vs. equity: why both matter for wealth building
• The basics of depreciation, bonus depreciation, and cost segregation
• How STR tax treatment can differ from traditional long-term rentals (and what “material participation” means)

Key frameworks Michael covers:
✅ Amenities + design + experience = pricing power
✅ “Build the hotel” mindset (premium rent vs. base rent)
✅ Forced appreciation through smart renovations
✅ Cost segregation + bonus depreciation concepts
✅ What to consider before selling (recapture + 1031 context)

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

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From One to Many: The Roadmap to Becoming a Professional PM - Hospitable Conference

Ready to scale from 1 property to a true short-term rental business? In this workshop, Tony Hughes (Hospitable Customer Success) breaks down the mindset shifts, lead-gen channels, and systems you need to grow from “host” to “operator”—without burning out.

You’ll learn practical ways to find new properties, win owners over, and set up sustainable operations as you add doors.

In this session, you’ll learn:
• The key mindset shift: treating hosting like an operation, not a hobby
• How Tony found his first co-host client using Zillow
• Lead sources that work for finding owners:
• Zillow (furnished rentals, bad photos, long time on market)
• FOIA STR permit lists (US-specific)
• Facebook groups (value-first approach)
• Airbnb Co-Host Network (how to stand out + qualify leads)
• The “UI Method” (finding underperforming high-earning listings)
• What to clarify upfront with owners (supplies, cleaners, maintenance, taxes, expectations)
• Common mistakes to avoid (complex pricing, unclear agreements, undercharging)
• How Hospitable can support co-hosts/PMs with AI replies, Knowledge Hub, owner portal, statements, invoicing, and smart device connections

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

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Aesthetic ROI: How to Redesign Your STR for Maximum Bookings - Hospitable Conference

Want to earn more per night without just “hoping” bookings show up? In this session, Jordan McDonough breaks down how aesthetics + strategy = real ROI in short-term rentals—so your listing stands out, attracts better guests, and commands premium rates.

Jordan shares real case studies (before/after), the shift to a more competitive “pro host” era, and the 5 marketing strategies that turn design into revenue—not just pretty pictures.

In this session, you’ll learn:
• Why STRs are entering a more professional era (and what that means for hosts)
• How design becomes a financial strategy (not a décor hobby)
• The difference between “average properties” vs. top 1% listings
• Real case studies showing ADR + revenue lifts from strategic design
• The 5-part marketing framework: target guest, experiential design, amenities, branding, photography

Key takeaways Jordan covers:
✅ Clear target audience (design for them, not you)
✅ Experiential design + local inspiration
✅ High-impact amenities that guests don’t get at home
✅ Property branding that builds trust + repeat/direct bookings
✅ Photography strategy (styling, lifestyle, post-production)

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

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Hospitable AI Masterclass

Want to stop living in your inbox and start using AI to run your hosting business smarter? In this masterclass, Ethan Brown (GM, Asia Pacific at Hospitable + STR host) demonstrates how to use Hospitable’s AI tools to save time, improve guest experiences, and prevent issues before they turn into bad reviews.

This is a hands-on walkthrough of the AI features hosts use daily to keep communication fast, accurate, and scalable.

Covered in this masterclass:
• Issue Alerts: how AI flags high-risk conversations (so humans can step in fast)
• Suggest with AI + Improve with AI:
• write better guest messages in seconds
• use prompts OR refine your draft instantly
• AI Guest Summaries:
• see what a guest cares about based on their review history
• personalize stays (and earn better reviews)
• Inbox AI / Auto Reply:
• how to configure delays, schedules, escalation rules, and fallback messages
• when to keep AI on 24/7 vs after-hours only
• how escalation works for urgent situations
• Knowledge Hub (the #1 takeaway):
• train the AI using your property info, PDFs/guidebooks, and common Q&As
• reduce repeat questions forever by centralizing answers
• Co-pilot:
• ask questions about performance, revenue, and property details like ChatGPT
• Reviews with AI:
• draft and post review responses quickly and consistently

Ethan’s #1 takeaway:
Spend time updating your Knowledge Hub—it’s the highest leverage work you can do because it improves every AI feature (auto-reply, suggested responses, accuracy, and consistency).

👍 If you’re curious about automating guest messaging without losing personalization, this is your blueprint.
💬 Comment “AI” if you’re already using auto-reply—or “STARTING” if you’re turning it on after watching.
============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

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https://twitter.com/hospitable

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5 Things You Can Do Today to Increase Direct Bookings - Hospitable Conference 2026

Direct bookings don’t happen by accident - this session shows 5 practical moves to start getting them.

Arthur (StayFi CEO) walks through a direct-booking playbook designed for Hospitable users: how to collect guest data ethically, leverage the “billboard effect” on OTAs, build brand touchpoints throughout the guest journey, automate remarketing, and tighten your “book direct” value proposition so guests actually convert.

What you’ll learn:
• Why direct bookings matter: control, repeat guests, and reducing OTA fee exposure
• Step 1: collecting guest data for repeat booking + upsells (email/SMS-ready)
• Step 2: using the billboard effect (brand cues inside OTA listings—without being spammy)
• Step 3: branding the guest journey (7+ touchpoints guests remember)
• Step 4: automated marketing sequences (arrival, post-stay, drip campaigns, anniversaries)
• Step 5: making “book direct” irresistible (pricing parity + perks beyond discounts)
• StayFinder overview: a meta-search approach that routes guests to direct booking sites

Speaker:
Arthur Colker — StayFi

Links & resources:
• StayFi: https://stayfi.com/
• StayFinder: https://www.stayfinder.com/
• Hospitable: https://hospitable.com/

#DirectBookings #VacationRentalMarketing #ShortTermRental #Hospitable #StayFi

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

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https://twitter.com/hospitable

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Tax & Compliance Map for US Short-Term Rentals

Understanding taxes starts with knowing what applies to you, and what doesn’t. In this session, we are looking at the broader tax and compliance landscape for US-based short-term rental hosts, with a focus on how investors and experienced operators approach compliance decisions.

This event features Amanda Han and Matt MacFarland, both Managing Directors at Keystone CPA, and is hosted by Brandon Huetteman, Hospitable’s Accountant in Residence. Together, they are sharing how tax professionals think about STR planning, structure, and common red flags, all before things get complicated.

We’ll cover:

- How STR activity is generally treated from a tax perspective;
- The STR “loophole”, how it’s commonly misunderstood, and the red flags hosts should be aware of;
- Business structure considerations, including the role of LLCs;
- How experienced investors approach tax planning and compliance.

The session begins with a guided discussion, followed by ample time for moderated Q&A.

About:

Amanda Han and Matt MacFarland are founders of Keystone CPA, where they advise real estate investors on tax strategy, structuring, and long-term planning. As both CPAs and investors, they focus on helping hosts and investors keep more of what they earn through thoughtful entity setup and tax planning. They are co-authors of the bestselling book "Tax Strategies for the Savvy Real Estate Investor", and frequent speakers and contributors across the real estate investing community.

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

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Hosting Smarter: Using Airbnb’s Tools to Stand Out - Hospitable Conference 2026

Want more Airbnb visibility in 2026? This session covers what actually moves the needle.

Tara (Airbnb Senior Market Manager) shares 2026 travel trends plus practical, host-friendly strategies to stand out in Airbnb search—focused on the biggest drivers of ranking: price, quality, and popularity. You’ll also see where to find Airbnb’s performance/insights tools (including listing issues, opportunities, and booking conversion metrics), and how Hospitable plans to surface key optimization actions in one dashboard.

What you’ll learn:
• 2026 travel trends: nature (“touch grass”), event-driven demand, and Gen Z value sensitivity
• How Airbnb search prioritizes: price, quality, popularity (and variety)
• How to use Airbnb’s “Compare your price” map tool
• Quality signals: photos, reviews, guest experience, cancellations, customer service
• Guest Favorites: what it is, how it’s earned, and why it matters
• Where to find the Listing Issues + Opportunities dashboards
• Availability tactics: booking window, lead time, minimum nights (and how to adjust in Hospitable)
• Booking conversion metrics: impressions → views → bookings + benchmarking

Speakers:
Tara — Airbnb
Miles — Hospitable

Links & resources:
• Hospitable: https://hospitable.com/
• Hospitable Community (post-session questions): https://community.hospitable.com/hospitable-workshop-days-51/day-2-hosting-smarter-using-airbnb-s-tools-to-stand-out-1078?tid=1078&fid=51

#AirbnbHost #VacationRental #ShortTermRental #Hospitable #AirbnbTips

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

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Power-Up Workshop: Metrics

In this live Power-Up Workshop focused on Metrics, the Hospitable team demonstrated how to unlock the full value of your performance data and understand what’s available on each subscription plan.

In this practical, step-by-step session, you’ll learn how to:

- Navigate the Metrics dashboard. Understand where to find all your key performance insights and how each section helps you make informed decisions.
- View and compare important performance metrics. Track trends in occupancy, revenue, booking windows, nightly rates, and more - across individual listings or your full portfolio.
- Understand feature availability by plan. See which Metrics views, filters, and insights are included in your current plan and what becomes available when upgrading.

By the end, you’ll be equipped to confidently analyze your business performance, identify opportunities, and use data-driven insights to optimize your strategy - no guesswork required.

Timestamps:
0:00 - Introduction
2:00 - Agenda
3:40 - Metrics dashboards demo
17:56 - Access by plan
20:45 - Q&A

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Short-term and mid-term rental hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

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Owner Management Power-Up Workshop

The Hospitable team did a live Power-Up Workshop focused on Owner Management, covering everything you need to confidently manage owners, commissions, and payouts in Hospitable.

In this practical, step-by-step session, you’ll learn how to:

- Create and manage owners. Add owners to your account and organize properties for seamless collaboration.
- Set up commissions and payouts. Automate your earnings distribution with flexible commission settings and transparent owner payout workflows.
- Generate and share owner statements. Keep everyone informed with clear, professional financial summaries.
- Share the Owner Portal. Give your owners on-demand visibility into performance, bookings, and income.

By the end, you’ll have everything in place to run owner management like a pro - saving time, reducing errors, and building trust with your partners.

Timestamps:
0:00 - Introduction
1:40 - Agenda
4:15 - Owner Management Demo
29:01 - Accounting for Property Managers
43:55 - Q&A

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

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Power-Up Workshop: Listing Management

Explore our latest tools for creating, editing, and syncing listings across multiple channels — all within Hospitable.

In this step-by-step session, you’ll learn how to:

- Create new listings directly in Hospitable with ease, from setup to publishing.
- Manage listings across channels — keep Airbnb, Booking.com, and Vrbo perfectly aligned.
- Use new configuration tools to customize content, availability, and rates without leaving the platform.
- Simplify your workflows so your listings stay consistent, optimized, and ready to perform.

Whether you’re launching your first property or managing a growing portfolio, this session will show you how Hospitable’s new listing management features save time, reduce errors, and help your business scale smoothly.

Timestamps:
0:00 - Introduction
5:43 - What is listing management
8:50 - Why you need to manage your listings
21:35 - Listing management demo
38:12 - Upcoming listing management features
41:00 - Q&A

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

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Dynamic Pricing Power-Up Workshop

Manually setting nightly rates—or sticking with static pricing—could mean leaving money on the table. Hospitable’s Dynamic Pricing takes the guesswork out, so you can boost earnings while saving time.

In this live workshop, our team guides you through how to get the most out of Dynamic Pricing and answers your questions along the way.

What you’ll learn:
- How to preview rates up to 180 days in advance and stay ahead of market trends
- Using Dynamic Minimum Stays, custom Rule-Sets, and a Far Future Premium to fine-tune your strategy
- Leveraging real-time market data with Hospitable’s proprietary pricing engine
- Seamlessly managing everything in your Hospitable calendar

Why it matters:
Hosts using Dynamic Pricing are already seeing results - an average 20% higher occupancy and 14.5% RevPAN increase across more than 7,000 properties.

Whether you’re new to Dynamic Pricing or looking to refine your approach, this interactive session will give you practical, revenue-driving strategies you can apply immediately.

Timestamps:
0:00 - Introduction to Smart Pricing
10:00 - Smart Pricing Demo
28:45 - Preview Smart Pricing
32:30 - Q&A

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

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Airbnb Power-Up Workshop

The Airbnb team and Hospitable’s own Andrew Schorr ran a hands-on virtual session designed to help your listings shine.

You’ll learn:
- The latest improvements from the Airbnb team
- How to boost your listing performance
- All the latest updates Hospitable has rolled out to make managing Airbnb easier than ever

Whether you’re just getting started or looking to optimize, this workshop will give you actionable insights to drive more bookings.

👉 Don’t miss it—your listings (and calendar) will thank you.

Timestamps:

0:00 - Introduction
1:19 - Tips for success on Airbnb (according to Airbnb)
3:17 - Quality as a success lever
5:28 - Factors that drive quality
10:14 - Improve listing appeal
17:33 - Competitive pricing
25:37 - Learning from listing issues
27:23 - Increasing availability
28:11 - Cancellation policies
30:29 - Applying discounts
31:12 - Airbnb fee changes
36:40 - Q&A

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

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Scaling to Success: Insider Strategies from 20 Listing Hosts hosted by Hospitable

Watch a power-packed, interactive host panel where experienced short-term rental entrepreneurs reveal the exact playbook they used to grow from a single property to 20+ listings. In this dynamic Q&A session, our panelists will dived deep into:

- Market Mastery: How to identify and evaluate high-yield markets before investing
- Design That Converts: Tips for creating standout listings that drive bookings (and Instagram buzz)
- Operations 101: Streamlined processes and tech tools to manage dozens of properties without burnout
- Team Building Timing: Recognizing the right moment—and roles—to start hiring support
- Max-Rate Monetization: Proven tactics to command peak pricing while consistently earning 5-star reviews
- AI Integration: Leveraging artificial intelligence to automate guest communications, dynamic pricing, and operational tasks—knowing when to implement AI tools and how to balance automation with a personal host touch

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

Watch video

How to Rank Higher, Book Smarter, and Attract Your Ideal Guest

In this hands-on workshop, we are demystifying the algorithm, teaching you how to audit your listing like a pro, and walking you through defining your Ideal Guest Profile (IGP) using a smart AI agent built by Hospitable.

You’ll learn exactly how to tailor your:

- Photos
- Listing headline
- Description
- “About this space” section
- Amenities list
…to magnetically attract the guests who are most likely to book—and rave.

Every host will walk away with:

- A fully generated Ideal Guest Profile based on your own guest reviews
- 10 AI-powered headline optimizations to boost visibility and conversions
- Tactical edits to turn your listing into a booking machine
- This isn’t theory. It’s a practical, ROI-focused overhaul of your listing using the data you already have.

Before the webinar: Have at least a free account of ChatGPT as this will be required to use the Hospitable AI Agent.

Timestamps:
0:00 - Introduction
6:04 - Ranking factor 1: Booking Conversion Rate
9:39 - Ranking factor 2: Click-Through Rate
11:15 - Ranking factor 3: Competitive Pricing
13:48 - Ranking factor 4: Guest Reviews & Ratings
15:17 - Breaking down a review request
26:14 - Ranking factor 5: Instant Book
28:21 - Ranking factor 6: Response Rate & Speed
29:24 - Property Knowledge Hub
32:20 - Ranking factor 7: Acceptance & Cancellation Rate
33:54 - Ranking factor 8: Listing Content Quality
37:04 - Ranking factor 9: Calendar Availability
39:17 - Ranking factor 10: New Listing Boost
39:52 - Live listing improvement
53:23 - Q&A

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

Watch video

Booking.com Power-Up Workshop

The Booking.com team and Hospitable’s own Andrew Schorr did a hands-on virtual session designed to help your listings shine.

✨ Highlights from the session:

- The latest improvements from the Booking.com team
- How to boost your listing performance
- All the latest updates Hospitable has rolled out to make managing Booking.com easier than ever

Whether you’re just getting started or looking to optimize, this workshop will give you actionable insights to drive more bookings.

Timestamps:
0:00 - Introduction
1:16 - Listing with Booking.com
16:02 - Creating a listing from Hospitable
18:02 - Managing and updating listings
24:00 - What we are building next
28:20 - Q&A

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

Watch video

Guest Portal Power-Up Workshop

In this Hospitable Power-Up Workshop, we took a deep dive into one of Hospitable’s most powerful tools for short-term rental guest experience: the Guest Portal.

Timestamps:
0:00 - Introduction
2:30 - A Better Guest Experience
8:18 - The New Guest Portal Demo
29:10 - Guest's View of the Portal
37:38 - Managing Guest Tasks
46:15 - Q&A

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

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Insights in the US Short-Term Rental Market for 2025

Welcome to this pre-recorded Hospitable webinar, where we team up with PriceLabs to deliver an in-depth look at short-term rental market trends across the US in 2024 and 2025.

🎙 Hosted by Miles from Hospitable and featuring Kyle Driskell, Senior Solutions Consultant at PriceLabs, this session is packed with actionable data and strategic insights on:

✅ Occupancy trends
✅ ADR (Average Daily Rate)
✅ RevPAR (Revenue per Available Room)
✅ Booking window compression
✅ Length of stay (LOS) shifts
✅ Urban vs. Rural market dynamics
✅ Preparing for major events like the 2026 FIFA World Cup

📍Case studies include:
• San Diego, CA: High summer occupancy & Comic-Con impact
• Joshua Tree, CA: Seasonality & shorter rural stays

🎯 Whether you’re a seasoned host, property manager, or exploring dynamic pricing, Kyle breaks down complex data to help you apply key takeaways to your specific market and property type.

💡 Learn why booking behavior is shifting, what to expect as we close out 2025, and how to position your listing for major revenue opportunities.

📬 Questions or want to explore PriceLabs?
👉 [email protected]

🔗 Useful Links:
Hospitable: https://hospitable.com
PriceLabs: https://pricelabs.co

👍 Like this video if you find it helpful, and don’t forget to subscribe for more short-term rental tips and webinars!

#ShortTermRentals #DynamicPricing #Hospitable #PriceLabs #VacationRentals #STRMarketing #FIFAWorldCup2026 #AirbnbTips #RevPAR #OccupancyTrends #RevenueManagement

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

Watch video

Direct Booking Power-Up Workshop

We held a hands-on workshop designed to help you get the most out of Hospitable’s Direct Booking tools, including actionable strategies to grow your revenue.

✨ Highlights from the session:

- A guided tour of Hospitable’s Direct Booking site builder.
- See how easy it is to create a stunning, guest-ready website in minutes.
- How to configure payment processing, guest vetting, and automated messaging to build trust and streamline operations.
- Set up custom policies, upsells, and promo codes to enhance your guests’ experience (and your margins!).
- Tips on connecting a custom domain, optimizing your listing for SEO, and integrating analytics tools.
- Marketing strategies to drive traffic to your site and turn first-time guests into loyal bookers.

🔗 Whether you’re just launching your direct site or want to maximize what you already have, this session will give you the confidence and clarity to own your guest journey.

Timestamps:
0:00 - Introduction
2:32 - Direct Premium plans
7:40 - Creating a Direct booking website
13:20 - Setting your booking policies
15:09 - Google Vacation Rentals
18:15 - Supercharging your Direct bookings
20:22 - Tips for getting Direct bookings
37:05 - Q&A

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

Watch video

Scale Without Stress: Automate Noise & Smoke Monitoring in Your STR with Alertify & Hospitable

🎥 In this on-demand webinar, Miles from Hospitable sits down with Melissa from Alertify to tackle one of the biggest challenges in short-term rentals: how to scale efficiently without burning out.

💡 Learn how to:
- Automate guest messaging and communication with Hospitable’s AI-powered PMS
- Prevent noise complaints, parties, and costly damages using Alertify’s monitoring tools
- Customize property-level thresholds, alerts, and guest messaging sequences
- Automatically send guest alerts and generate incident reports to protect your bottom line
- Screen guests in advance using Welcome Link to prevent fraud and high-risk bookings

🔧 Whether you’re managing one property or 50, this session dives deep into how the right tech stack can help you stay lean, save time, and run your business proactively—not reactively.

🚨 BONUS: Get 20% off your Alertify system with the code HospitableFriends20 — plus access Welcome Link FREE for the first year!

👉 Learn more or book a demo with Alertify here: alertify.io/book-a-demo/

—

👍 Like this video? Subscribe to our channel for more webinars, product tips, and host success stories from the Hospitable community.

#shorttermrentals #propertymanagement #Hospitable #Alertify #STRtools #vacationrentalautomation #guestexperience #noisemonitoring #airbnbhost #automateyourbusiness

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

Watch video

Hospitable and Zapier Power-Up Workshop

We dove deep into Hospitable’s new Zapier integration - and the possibilities are game-changing for short-term rental operators at every level of tech-savviness.

✨ Highlights from the session:
- Overview of Zapier and how it enables you to connect Hospitable with 8,000+ apps—without writing a single line of code.
- A walkthrough of our new Zapier triggers (reservations, messages, reviews, and properties) and actions (send messages, reply to reviews, etc.)
- Live demo: How to automatically log reservation data into Google Sheets—no manual entry needed.
- Advanced automations from @Sean McGregor of NoCodeSTR:
- Automate SMS messages, guest onboarding, and cleaner notifications.
- Set up smart filters using AI to reply to guest messages or handle review workflows.
- Trigger branded review follow-ups and Google review requests using Zapier AI and Airtable.
- Creative use cases for marketing: auto-send birthday discounts, post Canva-style reviews to social, and nurture 5-star guests into direct bookers.
- Real talk on tech stack: how Sean runs 67 properties for under $150/month using Hospitable + Zapier + Airtable + OpenPhone + more.

💬 Bonus: Robust Q&A covering WhatsApp support, Make.com vs Zapier, collecting guest data for marketing, and more.

🔗 Whether you’re automating your first task or scaling to 100+ listings, this workshop has practical gems you can implement right away.

============================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/47WgnFD

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in.

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

Watch video

Market Pulse: US Short-Term Rental Trends

Short-term rental data experts Key Data joined us for this live session, which looked back at 2024 US market trends and ahead to what we might see in Q1 2025.

Learn more about the current market dynamics, how they may impact YOUR rental performance, and what you can do to react.

Timestamps:
0:00 - Introduction
1:56 - Agenda
3:36 - Key Performance Indicators
15:40 - Homeowner Communication
16:35 - Stay Length Data
19:57 - Booking Window Data
23:57 - Booking Sources Data
27:36 - Key Takeaways
30:35 - How Keydata Differs from Airdna
32:00 - Q&A

Watch video

Summer Safety Tips for Your STR with Breezeway and Hospitable

During the warmer months of the year, ensuring the safety and comfort of your guests becomes even more crucial. We are excited to have Justin Ford, Director of Short-Term Rental Safety & Certification Programs at Breezeway, with us. With his extensive expertise in short-term rental safety, Justin will provide invaluable insights and practical tips to help you maintain a safe and enjoyable environment for your guests, protect you from litigation, and actually grow your short-term rental bookings.

From outdoor safety measures to emergency preparedness, this webinar will equip you with the knowledge to protect your property and enhance your guests’ experience during the summer season.

Timestamps:
0:00 - Introduction
6:53 - Short-Term Rentals Injury Statistics
9:16 - Vacation Brain and Other Dangers
13:47 - Firepit Risks and Safety
22:16 - Grilling Risks and Safety
32:27 - Examples of Possible Safety Issues in an STR
39:12 - Smoke Alarms in Short-Term Rentals
46:02 - Garage Risks and Safety
48:21 - Short-Term Rental Safety Codes
50:04 - Safety as a Marketing Advantage
53:20 - Breezeway Safety for Short-Term Rentals
56:35 - Breezeway Safety Course

Watch video

Market Pulse: A Snapshot of the Short-Term Rental Market with Key Data

Discover the latest insights into the North American Short-Term Rental market with experts from Key Data and Hospitable. This engaging webinar is designed to help hosts stay ahead of current market dynamics and optimize their rental strategies.

Timestamps:
0:00 - Introduction
3:30 - Short-Term Rental Data for the US Market
7:10 - Adjusting Your Rates Based on Demand
8:40 - Average Daily Rates Global and US Data
10:49 - Revenue per Available Rental Unit (RevPAR)
12:35 - Short-Term Rental Homeowner Communication About Trends
13:26 - Average Length of Stay
15:25 - Booking Windows Metric
17:32 - Understanding Booking Sources
19:00 - Short-Term Rental Reports to Watch
21:00 - Key Takeaways
22:55 - Key Data - Hospitable Integration
26:24 - Tracking short-Term Rental Market Saturation
27:55 - Why Is RevPAR Important?
30:00 - Key Data Pricing
31:16 - Competitor Comparison Data
35:17 - Key Data vs AirDNA
38:55 - Key Data Revenue Manager
43:10 - Key Data Markets

Watch video

Hospitable x The Host Co: Increasing Revenue Beyond Average Daily Rate

This webinar invites Annie Sloan of The Host Co to share her insights with Hospitable Hosts on upselling and showcase this latest integration.

Annie Sloan is Co-Founder and CEO of The Host Co, the hospitality platform connecting local amenities to short-term rentals - from massage and chef to fresh flowers, bike rentals and beyond.

Timestamps:
0:00 - Introduction
4:17 - Upselling for short-term rentals
7:05 - The benefits of vacation rental upsells
11:58 - Automating AirBnB upsells
14:13 - The Host Co demo
27:28 - Hospitable integration

Watch video

Tax Savings for Short-Term Rental Hosts

This webinar invites tax-saving experts Amanda Han and Matt MacFarland from Keystone CPA to share their insights with Hospitable hosts on correctly filing tax returns for their short-term rentals and ensuring they are not overpaying.

Timestamps:
0:00 - Introduction
5:42 - 1099K challenges faced by STR hosts
13:01 - Reporting expenses
15:00 - Best record-keeping practices
17:58 - Software recommendations for record-keeping
19:35 - Active vs passive income
24:17 - Tracking time spent on property management
25:51 - Tax loophole benefits for managers non-owners
27:00 - Cancellation reporting on declared income
28:24 - Consolidating income and expenses for tax reporting
30:05 - The common taxation mistake STR property owners make
31:24 - Short-term rental loophole
32:30 - Transaction threshold for 1099K
33:33 - Tax returns remittance to owners
34:58 - Hotel business rule
37:00 - Filing general expenses with multiple properties
40:02 - Having your name on title to write off the mortgage for the AirBnB
41:00 - Writing off a solar grid
42:09 - Property depreciation
43:07 - Bonus tax depreciation
45:31 - Documenting the time spent on your STR
48:14 - Doing cost segregation right
51:10 - Expensing depreciation vs appreciation on sale
55:14 - Bonus depreciation after the 1st year
56:23 - Deducting your personal expenses as business expenses
58:40 - Ideal structure for managing multiple STRs

Watch video

Adding Amenities to Increase Vacation Rental Bookings and 5-Star Reviews

This webinar invites experts from Mount (https://rentmount.com/), Minoan (https://minoanexperience.com/), and HostGPO (https://hostgpo.com/) to share their views, tips, and ideas on amenities. This panel discussion has been put together to help Hospitable Hosts discover ways to grow their short-term rental bookings and garner more 5-star reviews.

We discuss everything from the must-have amenities considered standard by guests to the luxury additions that can offer an unexpected surprise to a guest’s stay. We’ll also go beyond amenities in the property and discuss how experiences can also boost business without being labor-intensive for the host.

Timestamps:
0:00 - Introduction
5:08 - The importance of amenities for short-term rentals & must-have essentials
12:32 - Examples of local experiences to help boost the overall guest experience
17:13 - Knowing and catering to your target audience
19:06 - How to pick the right amenities for your target audience
23:40 - How to maintain amenities
28:50 - How to use amenities to increase short-term rental bookings
30:40 - The most popular amenities on AirBnB - do you need them?
34:30 - Generating AirBnB vacation rental revenue from amenities
37:47 - Masterclass guest recap
44:00 - Great coffee options as an amenity
46:30 - Should you charge separately for the amenities?
49:00 - Can Minoan help with a property that's already set
51:41 - How to get started with Mount
53:01 - Amenities insurance
55:45 - Key takeaways

Watch video

How to Screen Your AirBnB Vacation Rental Guests with Autohost

Airbnb vetting and coverage are not enough to protect you and your property. In this webinar with Autohost, we will discuss how Autohost's guest screening and other 3rd party products and software can help protect you, whether you are taking bookings on platforms like Airbnb or via a direct booking website.

This session will include a live Q&A segment for the audience to ask their questions.

#airbnb #shorttermrentals #vacationrentals #directbooking #bookdirect #propertymanagement

--------------------

Timestamps
0:00 - Intro & Welcome
3:54 - Extra Protection for The AirBnB Guest Vetting Process
8:15 - Cancelling a Potentially Problematic AirBnB Guest
11:07 - How to Protect Your AirBnB Vacation Rental from Damages and Fraud
13:56 - Screening Your Vacation Rental Guests with Autohost
16:04 - Protecting Your Short-Term Rental With a Hotel's Professionalism
20:56 - More Guest Screening Capabilities
24:19 - More Details on the Guest Screening Options for Vacation Rental Hosts
28:18 - Preventing Problematic AirBnB Guests with Instant Book
30:20 - Dynamic Vacation Rental Contracts with Autohost
31:16 - Vacation Rental Insurance and Guest Vetting
34:22 - Vacation Rental Protection with Autohost and Hospitable Integration
37:08 - How to Choose AirBnB Vacation Rental Insurance
40:56 - Screening Vacation Rental Guests Outside US with Autohost

Watch video

How to Decorate and Photograph Your AirBnB Vacation Rental with HostGPO

This webinar invites STR expert Jeff Iloulian from HostGPO (the buying group for hosts like you!) to share his insights with Hospitable hosts on how to create listings that stand out on direct booking websites and online travel agencies (OTAs) like Airbnb.

📌 Visit HostGPO’s website here - https://hostgpo.com/

📌 Looking for Jeff’s complete vacation rental checklist? Just click here - https://hostgpo.com/the-complete-vacation-rental-checklist/

#shortttermrentals #vacationrentals #howtohost #airbnb #vrbo #directbooking #bookdirect

--------------------

Timestamps
0:00 - Intro
4:43 - Creating Better Quality Vacation Rental Spaces with HostGPO
7:19 - Interior Design for AirBnB Vacation Rental Listing Success
10:10 - Cost-Efficient AirBnB Rental Interior Design
11:53 - Tips for AirBnB Vacation Rental Listing Success
13:19 - Local Aesthetic AirBnB Interior Design
13:45 - Sustainability in AirBnB Vacation Rental Interior Design
17:52 - What Is an Environmentally-Friendly Sustainable Stay on AirBnB
20:15 - How to Set Your AirBnB Vacation Rental Listing Up for Success
20:54 - Do You Need the AirBnB Guest Favorite Badge
30:58 - HostGPO Partner Brands
32:23 - How to Check the Ranking of Your AirBnB Listing
34:10 - Sustainable Stay ROI
36:13 - Short-Term vs Mid-Term Rental Listings
38:08 - Tips for AirBnB Listing Feature Photos
42:56 - How HostGPO Helps Vacation Rental Hosts
48:17 - Checking on Your Vacation Rental Business Competitors
49:56 - Tips for AirBnB Listing Photos Flow
52:38 - AirBnB Room Tour Feature - Good or Bad?
57:00 - Vacation Rental Industry Trends

Watch video

The Importance of Short-Term Rental Host Communities & Advocacy

This online workshop invites STR experts Theron Lewis of STRHero and David Krauss of Rent Responsibly to share their insights with Hospitable hosts on how to connect with other hosts, access resources, and lead short-term rental alliances.

--------------------

Rent Responsibly has a (near) comprehensive directory of Alliances here: https://www.rentresponsibly.org/alliances/

A to Z guide to help anyone with starting a successful alliance: https://www.rentresponsibly.org/diy-alliance/

For those trying to figure out what the heck to do with conflicting regs. This may help: https://www.rentresponsibly.org/how-to-figure-out-conflicting-vacation-rental-regulations/

Join Rent Responsibly to build the future of STRs (its free!): https://www.rentresponsibly.org/join/

Find out more about STRHero here: https://thestrregulationsguy.com/

--------------------

Timestamps
0:00 - Intro
9:35 - The Importance of Vacation Rental Host Communities for Advocacy
11:56 - When Should Short-Term Rental Hosts Get Involved in Advocacy
17:15 - Increase in Short-Term Rental Regulations and How to Affect Them
20:48 - How Short-Term Rental Hosts Can Start With Advocacy
29:24 - Starting an Alliance for Short-Term Rental Hosts
36:13 - Short-Term Rental Hosts' Hesitations about Advocacy
42:37 - Getting Involved with Regulatory Frameworks as a Vacation Rental Host
46:50 - Data vs Emotions in Short-Term Rental Advocacy
53:56 - What Short-Term Rental Hosts Can Achieve Through Advocacy
59:59 - Next Steps for Short-Term Rental Hosts to Get Involved with Their Communities

--------------------

If you enjoyed this event, why not join us for our other community events happening next week?

October 4th, 2023 at 9am PT - Hospitable Town Hall - Join the Hospitable.com team to hear about our company and product updates, and ask your questions! Add to calendar: https://calndr.link/event/y9iGxX3Pmp

October 4th, 2023 at 3pm PT - Hospitabuddies and Email Marketing - Join us for a collaborative community event with other Hospitable hosts. Explore Hospitable features, Q&A, and connect with your fellow hosts. Add to calendar: https://calndr.link/event/4meXNlISYI

#shorttermrentals #vacationrentals #STRadvocacy #airbnb #vrbo #bookdirect #STR #propertymanagement

Watch video

How to Increase Direct Booking Revenue with Dynamic Pricing for Short-Term Vacation Rentals

Got a question on how to price your direct booking property?

Richie Khandelwal, co-founder of PriceLabs, is here to help. Watch our direct pricing masterclass on August 30 at 7 am ET to get your questions answered.

#directbooking #bookdirect #shorttermrentals #vacationrentals #dynamicpricing

Timestamps
0:00 - Intro
4:58 - Data Parameters Used by PriceLabs for Dynamic Vacation Rental Pricing
8:14 - PriceLabs Pricing Model
9:25 - Tips for Pricing Your AirBnB Vacation Rental for Direct Booking
15:54 - How to Dynamically Price Your AirBnB Vacation Rental
19:48 - Market Conditions for the Optimal Vacation Rental Dynamic Pricing
21:15 - Using Local Market Intelligence for Vacation Rental Dynamic Pricing
25:35 - Mid-Term Booking Strategy and How PriceLabs Handles It
30:34 - Tips for Short-Term Rental Dynamic Pricing Strategy
31:09 - AirbBnb SmartPricing vs. PriceLabs
34:20 - PriceLabs vs Other 3rd Party Dynamic Pricing Tools
36:20 - How Does PriceLabs Set Pricing
38:58 - How Often Should You Check Your Vacation Rental Dynamic Pricing
40:23 - Pros and Cons of Aggressive Dynamic Pricing for AirBnB Vacation Rentals
43:54 - Setting Your Minimums for Vacation Rental Dynamic Pricing Strategy
45:23 - Short-Term Rental Pricing vs Mid-Term and Long-Term
48:29 - Last-Minute Dynamic Pricing Strategy for AirBnB Vacation Rentals
53:48 - Can You Trust Vacation Rental Pricing Engines' Forecasts
56:19 - Direct Booking Pricing for Vacation Rentals & Saving on Fees
1:00:40 - Positioning and Strategy for Price Negotiations for Vacation Rentals

Watch video

Financing your short-term rental in 2023

STR experts Daniel Ramirez and Adam Windham, Co-Founders of Host Financial, are joining us for this webinar to share their insights with Hospitable hosts on the best way to finance their vacation rentals endeavor. The webinar features a Q&A session after Daniel’s and Adams’s masterclass.

#shorttermrentals #str #vacationrentals #propertyinvestment #propertymanagement #financing

Timestamps
0:00 - Intro
4:34 - Financing Deals Offered by Host Financial
5:30 - Underwriting a Short-Term Rental vs a Long-Term Rental
6:35 - The Benefits of Investing in a Short-Term Rental
8:35 - Location-Based Strategy for Short-Term & Mid-Term Rentals
9:46 - Increased Competition & Short-Term Rental Market Conditions
12:20 - Metrics to Consider for Short-Term Rental Investment Decisions
15:47 - Diversification of Your Short-Term Rental Investment Portfolio
18:30 - Common Short-Term Rental Financing Mistakes
23:25 - Host Financial's Short-Term Rental Financing Requirements
25:22 - Loan Types Offered by Host Financial & Valuations
29:16 - Host Financial vs Standard Business Loan from a Bank
33:07 - Does Host Financial Work with Foreign Nationals for US Investments?
34:13 - Does Host Financial Work with Individuals or Companies?
36:00 - Does Host Financial Require Guarantors?
36:35 - Does Host Financial Operate as a Mortgage Broker?
38:55 - Scale-Up Challenges for Short-Term Rental Investors
40:56 - Does Host Financial Provide Financing for Arbitrage?
41:28 - Are Host Financial's Financing Programs Interest-Only?
42:38 - Host Financial's Average Rates
43:29 - Host Financial's Commercial Loans & Valuations
44:31 - Average Downpayments for Short-Term Rental Financing
45:04 - Does Host Financial Provide Fix & Flips Loans?
46:40 - Short-Term Rental Underwriting Requirements
50:33 - Does Host Financial Do DSCR Loans?
51:56 - How to Achieve Rapid Growth in the Short-Term Rental Market
57:19 - Getting Into the Short-Term Rental Investment Market

Watch video

Must-Know Tips for Mid-Term Rentals with WIIRE

Property investment specialists Grace Gudenkauf and Amelia McGeeis, Co-founders of WIIRE, are joining us for this webinar, all about the top investment and management strategies for MTRs and how women can support each other in the dynamic world of vacation rentals.

Website: https://www.womeninvestinrealestate.com
MTR Profit Academy: https://www.womeninvestinrealestate.c...
Use coupon code HOSPITABLE for 25% off!
Free Facebook Group: https://www.facebook.com/groups/wiire
WIIRE Instagram: @wiire.community
Amelia Instagram: @ameliajorei
Grace Instagram: @grace.investing

#midtermrentals #mtr #vacationrentals #propertyinvestment #propertymanagement #strategy #womensupportingeachother #womenforwomen #womeninvacationrentals

Timestamps
0:00 - Intro
4:14 - What Is a Mid-Term Rental?
5:02 - Switching From a Full-Time Job to Real Estate Investment
7:20 - BRRRR Strategy for Renta Properties
8:50 - How WIIRE Started
11:00 - Tips to Expand Your Rental Property Portfolio
15:09 - Using Hospitable to Manage Mid-Term Rental Properties
17:55 - Mid-Term Rental Guest Turnover
21:25 - Marketing Mid-Term Rental Properties and Finding Tenants
24:45 - Mid-Term Rental Market Development
26:19 - Switching Between Rental Strategies on One Property
31:52 - Tips on Furnishing a Mid-Term Rental Property
36:04 - Average Cashflow on a Mid-Term Rental Property
37:22 - Insurance Suitable for a Mid-Term Rental
39:00 - Offering Your Mid-Term Rental Property to Hospitals
40:28 - Arbitrage for Mid-Term Rental Properties
42:47 - How to Choose a Profitable Location for a Multi-Family Mid-Term Rental
44:12 - How Long Does It Take to Get Your First Mid-Term Rental Tenant?
46:20 - Understanding Demand and Competition in the Mid-Term Rental Market
48:15 - Adding Personal Touches to Your Mid-Term Rental
49:20 - How to Price a Mid-Term Rental Property
50:18 - Changes in Investment Strategy as Interest Rates Are on the Rise
51:20 - Managing Utilities for a Mid-Term Rental Property
52:19 - Creating Your First Mid-Term Lease Agreement
53:20 - Short-Term Rental Tenant Rights vs Mid-Term
55:15 - Creative Ways to Find Mid-Term Rental Tenants

Watch video

Growing from 1 to 250 properties with Avery Carl

STR expert Avery Carl is joining us for this webinar, all about growth and how to plan out for the long term with your short-term rental properties.

Timestamps
00:00 - Intro
00:07 - Introductions
5:40 - How did you get into short term rentals in the first place?
11:05 - How did you get over the initial hurdle of trying to buy a property and managing it remotely?
13:55 - How would you assess the value of a property?
20:15 - How has the STR market changed over the last 5 years?
25:06 - What does your team look like?
27:35 - Do you see any changes coming to the way people host, to set themselves apart from the competition?
33:49 - Which tools helped you start to expand the number of properties you managed?
44:05 - How were you able to get the capital to acquire so many properties?
48:47 - Are there any tips on identifying a good cleaner or a general contractor quickly upon entering a new market?
53:08 - What does a well performing short-term rental produce in net profit annually?
54:29 - If you’re looking at two (markets) how do you compare and choose?
55:50 - Including the pricing strategy around the used software.
56:38 - Outro STR expert Avery Carl is joining us for this webinar, all about growth and how to plan out for the long term with your short-term rental properties.

#shorttermrental #vacationrentals #dynamicpricing #propertyinvestment #propertymanagement

Watch video

The Future of Operations Automation with Turno

Do you want to learn more about the future of operations automation and how a service like Turno (turno.com) can help you with that?

Mike O’Connell, Head of Partnerships at Turno, and Stephan Bajaio, Chief Marketing Manager at Turno, share their expertise and insights with Hospitable hosts on how operations automation can help them manage their property easier and increase the bookings turnover.

Find out more about Hospitable's property management tools at www.hospitable.com

Sign up for our next Masterclass, "From 1 property to 250 in just 5 years: the secret to long term wealth" with STR expert Avery Carl, CEO and founder of The Short Term Shop, which will take place on June 29th. Register here - https://hospitable.zoom.us/webinar/re...

Are you interested in trying Turno for free? Hospitable customers connecting their accounts to Turno get their subscription for FREE. Find out more here: https://help.hospitable.com/en/articl...

Timestamps
00:00 - Intro
06:01 - What are the most common challenges that STR owners face when managing cleaning services of their properties?
12:55 - How can cleaning services automation help them solve these issues?
14:30 - Fun Game: Most ridiculous item found in a STR after a check-out
26:20 - When it comes to cleaners services, what are the recommendations on finding the right people?
33:50 - What are the short-term and the long-term benefits of automating hosting / property management operations?
42:39 - Audience Q&A
01:04:08 - Fun Game: Announcing the winner
01:09:26 - Outro

Watch video

How to build a vacation rental direct brand with StayFi

Do you want to learn more about creating a vacation rental direct brand and how a product like StayFi can help you?

Arthur Colker, Founder and CEO of StayFi, the #1 provider of WiFi marketing services for vacation rental companies, shares his experience on the best tips and tricks to ensure you get those valuable repeat bookings.

Find out more about Hospitable's property management tools at www.hospitable.com

Sign up for our next Masterclass, "The Future of Operations Automation” with Mike O’Connell, Head of Partnerships of Turno, which will take place on May 25. Register here - https://hospitable.zoom.us/webinar/register/WN_JBVJtngNTyyPzPHBmiWMRg

Are you interested in Hospitable's direct booking solutions? More info on our brand new product release rolling out now is here: https://hospitable.com/direct-booking/

Timestamps:

0:00 - Intro
4:06 - Why direct? Why should hosts be focusing on direct bookings?
7:28 - Why is it essential to create a brand image for direct bookings?
13:00 - What are some tips and tricks Hospitable Hosts can do to better their brand and increase direct bookings?
16:20 - How can a product like StayFI help STR hosts increase their direct bookings?
18:20 - Why is email marketing important in the STR business?
23:51 - What targets can you set when building your direct brand?
40:16 - Audience Q&A
52:56 - Outro

Watch video

Direct booking websites 101: How to build credibility

Chris and the I-PRAC team are kindly offering the Hospitable host audience a discount on their membership. Get 2 years of certification with I-PRAC for the price of 1.

------- Use the promo code HOSPITABLEDB101 at i-prac.com ------

Chris Maughan, STR Industry thought leader and owner of I-PRAC, International Property Rental Approval Certification shares expertise and insights with Hospitable hosts on creating trust and credibility with guests through their direct booking websites.

Find out more about Hospitable's property management tools at www.hospitable.com

Are you interested in Hospitable's direct booking solutions? More info on our brand new product release around the corner here - https://help.hospitable.com/en/articles/5845339-all-about-direct-bookings

Timestamps:

0:00 - Intro
04:50 Why to chose not to use any 3rd party OTAs and decided to use direct bookings from the start
24:30 Why is trust so important in the short-term rental industry?
33:00 Tips and tricks for building direct booking websites
26:45 What is trust marketing, and how can hosts use it to attract guests?
40:20 Audience Q&A
1:02:00 Outro

Watch video

How to get repeat direct bookings with Damian Sheridan

Do you want to learn how to get your guests eager to return for more and increase your repeat direct bookings for your short-term rental business? 👀

Damian Sheridan, Founder and Director of the Book Direct Show and the Scale Rental Show shares his experience on the best tips and tricks to ensure your getting those valuable repeat bookings.

Find out more about Hospitable's property management tools at www.hospitable.com
For more information on Damian’s fantastic work, you can visit his LinkedIn profile and if you’re interested in 5 Days of Unmissable Short-Term Rental Conferences & Events, check out the Short Stay Week in Barcelona from 15-19 May:

The Book Direct show - https://bookdirect.show/
The Scale Rental Show - https://scalerentals.show/
Damian Sheridan LinkedIn profile - https://www.linkedin.com/in/damiansheridan
The Short Stay Week - https://shortstayweek.com/

Sign up already for our next masterclass ""Direct booking websites 101: how to build credibility with the pioneer of trust, Chris Maughan" which will take place on 30 March. Register here - https://hospitable.zoom.us/webinar/register/WN_XRxwQYx_SZ6sjtRWyHsa1A

Are you interested in Hospitable's direct booking solutions? More info on our brand new product release around the corner here - https://hospitable.notion.site/hospitable/All-about-Direct-b358bebfb5604e5fb23ec95ecea6a670 -

Timestamps:

0:00 - Intro
4:06 - Why direct? Why should hosts be focusing on direct bookings?
7:40 - Damian's experience and how he got into direct bookings.
10:30 - repeat bookings vs net new guests
13:15 - How to use communication to increase repeat direct bookings
17:05 - Website design and SEO for direct bookings
21:30 - Advertising your property and growing your audience
23:23 - Loyalty rewards for repeat bookings and discounts for booking direct
28:00 - Challenges and risks for hosts starting with direct bookings
31:25 - Audience Q&A
52:56 - Outro

Watch video

How to avoid parties at your property with NoiseAware

Party hard 🎉🍻, but preferably not in your short-term rental 😉

Do you want to learn how to prevent incidents at your vacation rental properties? 👀

Patrick Arata, Senior Director of Customer Experience for NoiseAware shares the best insights on how to protect your properties without intruding on the privacy of their guests.

Find out more about Hospitable's property management tools at www.hospitable.com
For more information on NoiseAware's devices, go to: www.noiseaware.com

Timestamps:

0:00 - Intro
2:27 - Why should hosts install property management devices?
3:50 - Devices NoiseAware provides
6:18 - Should the guest or host be concerned about their privacy?
8:40 - What to do with the data from NoiseAware
10:50 - Indoor VS outdoor monitoring
12:48 - Setup and installation
14:20 - Occupancy tracking
16:00 - Network connection
17:05 - Audience Q&A
41:45 - Outro

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Hospitable Masterclass: Tips & Tricks for Short-Term Rental Investments with Tony J. Robinson

Our Hospitable Masterclass, "Tips & Tricks for Successful Short-Term Rental Investments", where Tony J. Robinson of Alpha Geek Capital shares his secrets on:

- How to analyze short-term rental investments
- How to establish long-term reliable partnerships
- Legal considerations when investing in rentals
- Investing in properties with heavy tourism
- Investing in out-of-state properties
- How to drive investment funding

and more!

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Hospitable Masterclass: Let’s talk about Trust: Guest Screening & Damage Protection

Check out this month's Hospitable Masterclass with Leo Walton, Co-founder and VP of Growth, SUPERHOG. Leo shares his valuable expertise on guest screening and damage prevention.

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Hospitable Masterclass: How to beautify your listings & attract more high-value bookings

In our next Hospitable Masterclass, "How to beautify your listings & attract more high-value bookings", Sarah Karakaian and Annette Grant of Thanks For Visiting share their secrets on expertly designing, staging and operating their short-term rental properties in order to attract more high-value bookings and augment revenue.

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Hospitable Masterclass: Mistakes to avoid when screening a short-term tenant

In our second Hospitable Masterclass, "Mistakes to avoid when screening a short-term tenant", Ela Mezhiborsky of Autohost shared her secrets for a successful guest screening. Ela is the Co-Founder and CPO of Autohost and handles the intersection of customer success and product development, setting priorities and driving the product roadmap. Before transitioning to SaaS, her career involved working in risk management, running her own digital marketing agency and managing a successful short-term rental business in Toronto.

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Hospitable Masterclass: How to boost your direct bookings: Tips & Tricks with Mark Simpson

Mark is the author of ‘The Book Direct Playbook’ and the founder of Boostly, an online association, and podcast, which aims to help hosts achieve more direct bookings. To date, Mark has worked with thousands of short-stay accommodation owners and helped them to skyrocket their direct bookings.

In this Masterclass, Mark will share how to:

Save thousands in commission costs
Stop wasting time learning complicated and outdated strategies
Build a hospitality business that is not reliant on third parties to be profitable
Take control of your destiny and attract your ideal guests to book directly through you

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Guest Portal Workshop: Set It Once, Earn From It Again and Again

In this workshop, we show you how successful hosts use Hospitable's Guest Portal to provide a polished experience from the moment a reservation is confirmed. You'll learn how to strategically place upsells like Early Check-In, Late Checkout, pet fees, and other add-ons where guests are most likely to take action.

We'll also cover simple automation strategies that ensure guests receive the right information at the right time, helping reduce support requests while increasing guest satisfaction and 5-star reviews.

You'll Learn
✅ Customize your Guest Portal with your branding

✅ Position Early Check-In, Late Checkout, and other upsells where guests naturally see them

✅ Automatically send Guest Portal messages throughout the guest journey

✅ Reduce repetitive guest questions with better organization and automation

✅ Create a polished guest experience that leads to happier guests and better reviews

Whether you manage one property or an entire portfolio, you'll leave with practical improvements you can implement immediately to save time, create a better guest experience, and generate more revenue from every stay.

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Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

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Get Your First Direct Booking

In this live workshop, we walk through exactly how to get your first direct booking using the tools you already have in Hospitable. You'll learn what to set up, what to avoid, and the small changes that make the biggest difference.

No complicated marketing funnels.

No expensive software.

No need to become an SEO expert overnight.

Just practical, actionable steps that you can implement immediately.

What You'll Learn:

✅ The fastest path to landing your first direct booking

✅ The biggest mistakes that keep hosts stuck waiting for "someday"

✅ Simple ways to let past and future guests know they can book directly

✅ How Hospitable's Direct Booking tools work together to make the process easier than you think

Whether your goal is one direct booking this month or building a long-term direct booking strategy, this workshop will give you the foundation to get started with confidence.

===========================
Find out more about Hospitable and get a 14-day free trial at https://hsptb.com/youtube

https://www.instagram.com/hospitable_com/
https://www.linkedin.com/company/hospitable/
https://www.facebook.com/hospitable
https://twitter.com/hospitable

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Type

Upcoming

(3)

Recurring

(1)

Past

(66)

UPCOMING EVENTS

Stop Answering the Same Guest Questions Every Day

What You'll Learn

✅ Build message templates that automatically personalize every conversation

✅ Use Smart Conditions to send the right message at the right time

✅ Save time with Custom Codes instead of manually updating messages

✅ Preview your guest journey before messages go live

✅ Create a messaging workflow that reduces repetitive questions and saves hours each week

By the end of the session, you’ll have a messaging system that saves time while delivering a consistent guest experience from booking through checkout.

Managing Your Owners, Statements, Invoices, and Payouts

Still spending hours pulling together spreadsheets, taking screenshots, and answering the same owner questions every month? There's a much easier (and far more professional) way.

We'll cover:

📊 Creating beautiful owner statements in minutes
💸 Managing payouts without the spreadsheet headache
🧾 Generating invoices for management fees and additional charges
📈 Giving owners the transparency they want while saving yourself hours every month
🤝 Tips for delivering a premium owner experience that helps you retain clients and grow your business

If you've ever thought, "There has to be a better way," this workshop is for you.

Join us and discover how to spend less time building reports and more time growing your portfolio. Your owners will appreciate the professionalism—and you'll appreciate getting your evenings back.

The 15-Minute Setup That Can Save You Thousands

No one starts hosting expecting a guest to throw a party, damage the property, or ignore the house rules... but every experienced host knows that sometimes, things happen.

The good news? One of the best ways to protect your business takes about 15 minutes to set up.

We'll cover:

📝 Creating and customizing your rental agreement
✍️ Automatically collecting electronic signatures before check-in
🛡️ Understanding guest verification and when to use it
⚖️ Reducing risk while setting clear expectations with every guest
⚡ Setting everything up in about 15 minutes

Join us and learn how a few minutes of preparation today could save you thousands tomorrow, while giving you greater peace of mind every time a new reservation comes in.

RECURRING EVENTS

Getting Started with Hospitable

Get up and running with Hospitable faster and learn the key workflows that successful hosts use every day.

Whether you're exploring Hospitable during your trial or you've recently signed up, this session will help you build a strong foundation and start seeing value sooner.

You'll learn how to:

Get your account set up
Connect your booking channels and review key settings
Automate guest communication and operational workflows
Avoid common setup mistakes
Make the most of Hospitable's tools, resources, and support