7 Ways to Drive Repeat Direct Bookings

Drive Repeat Direct Bookings

By The Hospitable Team

You’ve just had a great review from a vacation rental guest, you’ve built up a good relationship, and they even said they’ll come back to your rentals next year. Great! 

But how can you make sure they come back to you directly, so you don’t have to pay OTA fees over and over for the same guests? Especially when you’ve already done the hard work of building that good rapport and offering them a great stay?

The answer: Building a direct repeat booking strategy that really works.

It’s the best way to secure repeat guests and higher profits—by saving on OTA fees, improving guest loyalty, and boosting occupancy rates. 

And, you can make this process of securing repeat direct bookings by using dedicated automation software—so you can master a direct booking strategy without spending hours in front of a computer.

Here’s how.

Table of Contents 

       0. Why repeat bookings are so important in the first place

7 Ways to Drive Repeat Direct STR Bookings

Hospitable.com automates nearly 100% of your guest messaging.

And now, we’re building an end-to-end direct booking solution so you can extend your exceptional hospitality to direct guests.

Why repeat bookings are so important

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Repeat direct bookings can boost profits and increase business resilience

As you’ve likely discovered, direct bookings can be an excellent additional revenue stream for your business, and complement bookings from your various OTA distribution channels—and repeat guests are the best way to drive direct bookings.

Enabling repeat bookings via your own website also helps to: 

  • Boost profits by sidestepping OTA fees
  • Increase business resilience by offering bookings away from OTA algorithm changes
  • Build customer loyalty and foster good relationships with guests
  • Add professionalism and reliability to your brand
  • Increase ownership of your own business away from OTAs

Some vacation rental businesses will rely especially heavily on repeat guests, such as drive-to leisure destinations that families visit every year or season, or rentals used by corporate travelers who return to the same conferences year after year.

7 ways to drive repeat direct STR bookings (and beat OTA fees)

direct STR booking

It’s clear: Winning repeat direct bookings is fantastic for your business.

But there’s no denying that OTAs offer useful services, including showing calendar availability, payment processing, guest messaging, review requests, and email marketing—as well as some level of insurance and screening.

A good direct booking strategy will cover all these and more, so that when your guests book again, you both experience all the benefits of world-class OTAs.

Here’s how to prepare for direct, repeat bookings so you can successfully sidestep OTA platform fees—for more profit and less stress.

1. Build a great direct booking website

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You can embed Hospitable’s booking widget into your site to take direct reservations and sync with the OTAs

It almost goes without saying; you can’t take direct bookings (repeat or otherwise) without a functional direct booking website. Good direct booking website must-haves include: 

  • A domain name that is descriptive and easy to find (e.g. SallysVacationRentalsFlorida.com)
  • Strong branding, including colors, fonts, images, and amenities that appeal to your guests
  • A wide range of great photos and easy-to-read, detailed, and informative listings
  • A booking widget that shows your rentals, a calendar of availability, and clear rates
  • Connection to a payment processor that takes secure payments (such as Stripe)
  • A guest communication tool that contacts guests with booking confirmation and crucial info about their stay
  • An about page that explains who you are, your expertise, and why guests should book with you
  • Reviews from past guests who love your rentals via a widget or plugin (such as Revyoos.com)

Platforms such as WordPress, Wix, and Squarespace are a great place to start, and can offer domain name registration, hosting, design tools, booking and payment processor connections, and enable plug-ins for social media and reviews.

Pro tip. Hospitable.com Direct makes it even easier to build a great direct booking website and has all of Hospitable’s guest communication and automation tools built in—so you can reap the benefits of direct bookings without spending hours on set-up, or having to become a website expert overnight.

2. Give guests a five-star experience they want to repeat

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Giving guests an experience they can’t wait to repeat is the first step in ensuring return bookings

You can incentivize guests to book again by exceeding their expectations during their stay in the first place.

Some tried and tested methods to give guests a great experience include: 

  • Automating smart check-in and check-out – Make arrival and departure easy, secure, and stress-free by enabling smart locks (and sending the unique keycode to guests in advance).
  • Establishing great communication – Set up a messaging flow that builds excellent rapport right from the start, including check-ups throughout the stay. Hospitable.com’s automated messaging tools make this even easier, saving you hours compared to typing manual replies.
  • Tailoring your rentals to a specific ideal guest – “Niching down” may sound counterintuitive, but making sure your rentals respond precisely to a specific guest profile (such as fast WiFi and work station for a digital nomad, or a cozy hot tub for honeymooning couples) will offer an unrivaled experience.
  • Offering personalized gifts on arrival – Give guests a great first impression by leaving a handwritten note, welcome hamper, or (for example) plant-based treats if one of them is vegan.
  • Providing great in-room amenities – Make guests’ stay stress-free and welcoming by providing in-room supplies such as luxury or eco-friendly soap, local coffee, or popular snacks.
  • Responding promptly to messages and questions – Guests like to feel safe and listened to, and want responses fast if questions arise. Hospitable uses AI technology to respond to comment queries automatically, so you can reply quickly even if you’re not online.
  • Offering local recommendations and guides – Providing restaurant tips or insider knowledge on the best local attractions boosts your authority and is extra helpful for guests.
  • Providing excellent housekeeping – Using automated task scheduling tools can help to coordinate housekeeping and make sure your properties are always sparkling clean.
  • Keeping on top of maintenance and repairs – Make sure your rentals are always in top condition by scheduling regular checks on appliances, building work, and furnishings.
  • Asking for reviews and offering good reviews in returnAutomating review requests and promising to give good reviews helps build rapport and gives guests a chance to offer feedback.

3. Master your messaging flow to build strong relationships

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Establishing good communication with your guests is key to ensuring repeat bookings

We mentioned “great communication” in the list above, but guest messaging and communication are so important that they merit a bit more detail here. 

Long before you start emailing guests after their stay, you need to build up a good rapport first. This will impress guests, and make them feel cared for right from the start. 

Using tools such as Hospitable’s automated, pre-scheduled messaging function, and AI feature to answer common questions instantly, makes this even easier. You can pre-write messages and send them in small, digestible chunks at appropriate intervals.

We recommend the following STR message flow for the best guest experience


  • Complete, useful, and accurate listing descriptions that speak directly to your ideal guest
  • Well-maintained FAQs in your listings and on your site
  • Fast responses (within minutes) to questions and guest inquiries
  • Booking confirmation promptly after booking, with thanks and a notice of when guests can expect to hear from you (e.g. “I’ll be in touch a week before with more details”)
  • Questions to learn more about your guests so you can tailor the vacation experience to their needs and preferences
  • Guidebooks or local insights to help guests plan their itinerary or what to bring
  • Detailed arrival and check-in instructions
  • Message on the morning of check-in with confirmation, reminder of check-in details, and any other must-know information


  • Morning of arrival message containing the door code and WiFi password
  • Day after arrival check-up to ask for feedback, answer any questions, and give yourself a chance to iron out any early issues
  • Check-out reminder and thanks


  • Review request and further reminders if required
  • Invitation to book again directly through your website
  • Reminder to book again, especially timed to make sense (e.g. 60-90 days after, or 10 months after, when they may be preparing for another annual stay)
  • Follow-up messages via email to continue the relationship and invite repeat bookings (see below!)

Using Hospitable’s Direct website building service means that you can take direct repeat bookings, with all of its automated messaging capabilities included as standard. 

This makes the above flow far less time-consuming and far more effective (by scheduling messages to send at the exact right time).

4. Compile an email database for future messaging

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Capturing guests’ email addresses and communicating via email helps boost repeat business

Did your guests originally find you via an OTA such as Airbnb or Vrbo? Great! But it’s now up to you to make sure all of their future bookings are made through you directly.

As well as following the above tips, another major way to do this is by capturing their details when they book for the first time (especially email addresses) and adding these to your own database—which Hospitable can do automatically for you when a guest provides their email address.

Once you have your guests’ email addresses and consent (for example, GDPR laws in Europe mean you must have express permission to email guests with marketing updates), you can send guests regular news, deals, and discounts, to entice them to book again.

You could compile and store email addresses on an Excel spreadsheet, or invest in a popular email marketing platform (with even more powerful features) such as:

  • MailChimp
  • ActiveCampaign
  • MailerLite
  • HubSpot
  • AWeber

Each of these offers a variety of functions at various price points, depending on the number of email addresses you have and the capabilities you need for your business.

5. Continue good relationships with previous guests

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Updates on behind-the-scenes details such as how you’re getting your rentals ready for a new season can keep you visible to guests

A successful email marketing strategy will also go beyond simple sales tactics such as sending discounts or deals.

Sending regular emails with news, updates, or behind-the-scenes content—such as how you’re decorating for Christmas, getting ready for summer, or excited about a local event—will keep your place front of mind. (See point 6 below for even more update ideas!)

You can also time messages with key events, such as their birthday or anniversary, or seasonal holidays, for an even more personal touch.

Most email platforms will also let you schedule reminders to book annually, which may work especially well for families who come regularly for their summer vacation, or business guests who travel for yearly conferences. They’ll feel as though you’re emailing them directly, and that you truly appreciate them.

You can also send guests incentives to book through you personally, with tailored deals or arrival gifts only available via direct booking (such as a glass of Champagne on arrival, for example), or extra treats if they successfully recommend your rentals to friends and family.

All of this helps guests to see you as a real person or friendly business—in contrast to a more faceless OTA—which will make them more likely to book with you directly.

6. Build rapport further (and spread the word beyond OTAs)

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Filming yourself behind the scenes can make great social media content

You can think beyond email marketing when it comes to establishing a good rapport with guests after their stay, keeping your business top-of-mind, and making guests excited to come back.

Social media is an excellent way to do this. Head to the platforms that your ideal guests will use, and create content tailored especially to them (this will also act as great marketing for new guests too, incidentally!).

As well as posting regular deals or seasonal offers, you can also simply share more about you, your business, and your expertise. This helps to build “buzz” and entice guests to book again and again.

This might include posts or videos featuring: 

  • Local events or ways to enjoy your local area (e.g. why guests should want to come back)
  • Recent news or updates, showcasing your authority and expertise as a host
  • New amenities or features, such as a new hot tub or coffee machine, or updated smart devices
  • Behind-the-scenes insights, such as how you turnaround rentals for guests, new decor, or how you’re preparing for a new season
  • Details of your local suppliers, such as tours of the coffee roastery that provides your beans
  • Views or must-see parts of your area, to remind guests of why they love visiting your rentals
  • Excellent guest reviews, to establish social proof and remind people why your rentals are great

7. Reassure guests with extra security

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Investing in security measures can help guests feel safer, leading them to book again

Accepting bookings without OTAs means you sidestep their algorithm vagaries and fees (good), but also means you open yourself up to more risk (less good!).

OTAs such as Airbnb might admit that their “guarantees” don’t amount to proper insurance, but at least they offer some kind of protection, and ID verification helps protect your rentals to some degree. 

When taking direct bookings, you need to make sure you’re still protected as you would be when taking bookings via an OTA.

Protecting your business and guests includes: 

  • Taking out an appropriate vacation rental-specialist insurance policy (such as Safely or Proper) that provides coverage in the event of damage or injury
  • Implementing guest screening that uses AI (such as Autohost.ai, which integrates with Hospitable) to avoid bad guests, fraud, or criminal activity
  • Using smart locks that only give access to authorized users, and change their codes after each check-out (such as Schlage, which integrates with Hospitable) to improve security

You can make these elements clear on your direct booking website, to make sure guests understand your policies and offer them reassurance that you’re a professional operator they can trust. 

In the same vein, you might have a page on your website (or a disclaimer in the footer) about your cancellation policies, ways that you ensure guest safety, how you process payments, and how you store data securely.

This is part of building up a vacation rental brand, presenting a reliable and trusted front to guests, and showing them they can book directly through you risk-free (making them far less likely to revert back to an OTA). 

Driving repeat direct bookings: Automation is your friend

Get a direct booking website within minutes!

Our system will ensure your calendars stay synced with OTAs, and your guests get the best experience.

Driving repeat direct bookings is key to continuing great relationships with guests, boosting profit, and sidestepping OTA fees and algorithm changes. 

And to do this successfully, you need a strategy that works including ensuring you have a functional website, of course, but it also means giving guests a stay they truly want to repeat—and doing so in a way that’s scalable, which requires automation.

When it comes to coordinating your operations with the ideal guest experience, switching to Hospitable.com can help. 

Not only does our Direct website feature make it even easier to create a functional, beautiful website that works, but it also offers excellent guest communication tools, automated messaging, email address collection, smart lock integrations, and review management, to make the process a thousand times easier.

Improve your guest experience and build great relationships and keep them strong, so you can secure repeat direct bookings again and again—for a thriving business that doesn’t rely on OTAs to prosper.

Hospitable.com automates nearly 100% of your guest messaging.

And now, we’re building an end-to-end direct booking solution so you can extend your exceptional hospitality to direct guests.
Creating a direct booking website

Essential Steps to Creating a Website that Drives Direct Bookings

From setting up a direct booking website, taking great photos, showing calendar availability, taking payments, and sending confirmation emails—never mind making sure visitors actually see your site in the first place—it can feel like there are so many moving parts you barely know where to begin. We get it. But pushing past the overwhelm can literally pay off.

str message flow

How to Build the Perfect STR Message Flow To Boost Guest Experience

Automated message flows make it easy for you to instantly respond to inquiries, greet your guests once the booking is confirmed, answer questions quickly, upsell amenities, and deliver a well-rounded experience. This article will walk you through the ideal message flow for a typical STR guest.

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