Remote Management of Vacation Rentals: Customer Case Study

customer case study

By The Hospitable Team

Welcome to’s series of host case studies, where we take a deep dive into the unique experiences of our valued hosts. Through these inspiring success stories, we aim to showcase tips that can help you to succeed with your short-term rental business and better leverage your Hospitable subscription.

Taylor Adams,, Follow on Instagram

Boston, MA. With short-term rental properties in Tennessee, Texas, and Vermont 🇺🇸

Properties managed?
3 properties, managed remotely.

Favorite Hospitable feature?
Messaging automation - I love that I can send out emails about orphan nights (individual unbooked nights sandwiched between other bookings) to potential guests and increase our revenue without having to look at the calendar and manually message each guest.

The world of short-term rentals offers numerous opportunities for those seeking financial freedom. In this case study, we’ll explore how Taylor Adams and her husband, based in Boston, MA, made a strategic shift from long-term rentals to owning and managing a flourishing short-term rental business. Learn how they rely on and other automation tools to streamline operations, scale their business, and enjoy a work-optional lifestyle. This has given them the amazing opportunity to spend time with their 2-year-old and create the life they always imagined!

Meet Taylor

Taylor began her real-estate journey in 2018 with a house hack (house hacking means finding ways to generate income from your home such as renting units to others) just outside of Boston. Her passion for financial freedom began there and led her and her husband to expand their portfolio with long-term rental properties. 

They began investing out of state in long-term rental properties due to Boston being a high-cost-of-living area. Fast forward to 2020, the world shut down, Taylor was 4 months pregnant, and it was a turning point.

They decided to sell their entire long-term rental portfolio and invest in short-term rental properties. Now, the couple manages multiple properties in Gatlinburg, TN, Crystal Beach, TX, and Vermont (a recent addition to their property portfolio), all while enjoying a work-optional lifestyle.

The Challenge

 Managing a short-term rental business remotely without a team can be challenging. The biggest hurdles for Taylor and her husband were the learning curve of entering new markets, avoiding double bookings across multiple platforms, and streamlining communication with guests.

The Solution

To overcome these challenges, Taylor turned to Hospitable, a powerful all-in-one vacation rental management software. Our platform’s automation capabilities allowed them to manage their properties more efficiently and drive additional revenue.

Messaging Automation

Taylor’s favorite feature is Guest Experience. It enables her to automate messages to guests in her own voice. She can even automatically send emails to guests about individual nights between bookings (orphan nights) that would lose her revenue and ask potential guests if they would like to extend their stay to cover them (find out how you can do it too here). Far easier than manually messaging each guest.

By creating messaging specific to guests (instead of just automating a check-in/out message), Taylor and her husband can drive in more revenue.

Double-Booking Protection

Hospitable also helps Taylor avoid double bookings by seamlessly syncing calendars across multiple platforms, such as Airbnb and VRBO. Meaning that she can list in more places without spending more time managing those channels.

Additional Automation Tools

As well as using Hospitable to automate her messaging and calendar management, Taylor uses our integration with PriceLabs to set and update her pricing automatically. This dynamic pricing tool helps Taylor and her husband stay on top of trending pricing and adjust rates based on events or market demand.

Taylor and her husband plan to grow their short-term rental portfolio by adding five more properties this year. They will continue leveraging Hospitable to streamline their business and explore new features to enhance their operations further.

Property on laptop

Taylor’s journey from long-term rentals to a thriving short-term rental entrepreneur demonstrates the power of strategic thinking and leveraging automation tools like Hospitable. By embracing these technologies, Taylor and her husband have achieved a work-optional lifestyle, allowing them to focus on what matters most—spending quality time with their family. will facilitate your business growth.

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