Switching from Hostaway earned Flip Flop Vacation Rentals 95% booking rate and 4.96-star average

Founded by an active-duty army member and his partners, Flip Flop Vacation Rentals began by self-managing their own investment properties in Florida. What started as a cost-saving measure quickly turned into a full-service operation.

Initially managing their business through Hostaway, they found the system limiting as their portfolio grew. Listing setup was time-consuming, accounting processes were clunky, and integrations — particularly with QuickBooks — failed to deliver on their promise.

These frustrations, combined with their plans to expand, prompted the team to reevaluate their tools. After testing Guesty, the decision was clear.

Guesty’s automation tools immediately made an impact. Flip Flop was able to streamline communications using auto-messages and replies, turning common guest inquiries into fast, templated responses. They even turned a potential pain point — early check-in and late check-out requests — into a new revenue opportunity.

Compared to Hostaway’s manual-heavy messaging system, Guesty’s templates and duplications made it easy to scale their communications while maintaining their signature responsiveness.

With 10 listings and a 95% booking rate, Flip Flop Vacation Rentals is focused on strategic growth. They’ve begun onboarding new owners, using Guesty’s Owners Portal to simplify reporting, document sharing, and communication.

Guesty’s analytics also play a key role in their internal decision-making. With visibility into revenue trends, booking channels, and guest behavior, the team has the insights they need to make smart growth decisions.

Another area where Guesty has delivered is in enabling repeat business.

Flip Flop Vacation Rentals plans to add 3–5 new properties by the end of the year, with an eye toward hiring dedicated maintenance and guest communication support once they scale further. Guesty’s flexible platform and the time it saves has given them room to grow without compromising on service.