Building a Vacation Rental Business You Actually Own

By Mike Chen, Founder of FunStay Florida

I manage over 100 vacation rental properties across Central Florida. A few years ago I realized that, for all that growth, I did not really own my business. I had built it on third-party platforms like Airbnb and Vrbo, and when those platforms changed or stopped working for me, I saw how exposed that left us.

The 100+ Door Lesson

Scaling FunStay Florida past 100 doors taught me something I did not expect. Managing properties and building a business are two different jobs.

For the first few years I was heads-down doing what most property managers do. Adding doors, keeping guests happy, handling maintenance, tweaking pricing. The portfolio kept growing and so did revenue. What I was not watching was how dependent I had become on the platforms underneath me.

Our entire online presence ran through a website vendor. The booking site, the guest communication flow, the brand experience for direct bookings. All of it lived on someone else's platform, and for a while that was fine. At 10 or 20 properties you do not notice the cracks. At 100 doors every crack is a problem. When the vendor's system had issues, we had issues across every property. When their support could not keep up, neither could we.

I started asking myself a hard question. If this vendor disappeared tomorrow, what would I actually own? The properties, sure. But the website? The guest data? The booking flow? The brand I had been building online? None of it was really mine. It all lived on rented ground.

The answer was uncomfortable, and it is when I started thinking less about adding doors and more about what I actually controlled.

Moving Off the Vendor

We eventually left our website vendor and built our own online presence. It was not a quick decision and it was not painless. Migrating 100+ listings, rebuilding the booking flow, setting up a site from scratch while still running day-to-day operations. It was a lot of work.

It also forced us to face something. We had been confusing using technology with owning our business.

The vendor handled a lot for us: calendar syncing, booking pages, some automation. For a while that felt like enough. Then things started breaking at scale. Double bookings that damaged our credibility. Communication gaps where owners did not know what was happening with their properties. Hours on the phone with support to fix problems that should have been handled automatically. We had traded control for convenience.

Choosing reliable technology matters more than almost anything else when you run properties at scale. What took me longer to see is that there is a difference between using a technology partner and building your entire business inside one. If everything you have built lives on a single vendor's platform, you are one pricing change or one bad support experience away from starting over. We know, because we lived it.

A PMS Is a Tool

After that experience I started seeing the same pattern everywhere in our industry.

A property management system handles reservations, automation and operations. A good PMS does that well, and it matters. But a PMS is not a marketing engine. It does not drive traffic to your website. It does not get you found on Google. It does not build your brand in your market or give a guest a reason to book with you instead of scrolling Airbnb.

I have talked to property managers who spent years perfecting their PMS setup: automated messages, pricing rules, every workflow tuned. All important work. When I asked what they were doing to drive direct bookings, build an email list, or rank when someone searches for vacation rentals in their area, the answer was usually nothing.

They had a perfectly tuned machine with nothing feeding it. Every booking came from Airbnb and Vrbo, and if those platforms changed the rules, the whole thing would stop. That is exactly where we were before we made the switch.

Don't Rely on OTAs

Airbnb, Vrbo, Booking.com. I am not telling anyone to walk away from them. They bring eyeballs and bookings, especially early on, and we still use them.

But if 90% of your revenue comes from platforms you do not control, think hard about what happens when those platforms change. They always do. Algorithms shift overnight for reasons nobody fully understands. Commission structures go up. Search rankings move. You can do everything right and still wake up to half the impressions you had last month.

The property managers I know who actually sleep well are the ones who built a direct booking channel alongside their OTA presence. They have their own website, one they actually own. They have brand recognition in their local market. They have repeat guests who come back year after year without a commission on every stay.

Direct bookings save on commissions, and at 100+ doors those savings add up fast. The bigger win is control. When someone books directly with you, that is your customer. You have their email. You can reach out next season. You can ask for a referral. You can build a relationship that gets stronger over time instead of resetting to zero with every new Airbnb search.

Own Your Audience

Back when we ran everything through our website vendor, I thought having a booking site was enough. It was not, because the site was not really ours, and neither was the audience.

Build your email list. Build your guest database. Put real effort into your own website traffic, your content, your search rankings, your reviews, your brand. All of that is yours. No vendor can take it away and no platform change can erase it.

I see property managers pour money into technology and then wonder why direct bookings stay flat. A booking engine does not bring guests to your website. Something else has to do that. SEO, content that ranks when someone searches for rentals in your market, and the reputation you built through years of consistent service and five-star reviews. That is what creates demand. The technology processes it.

At FunStay Florida, building our own audience on our own website changed the business. It took time, and it was less satisfying in the short term than optimizing an Airbnb listing. But across 100+ properties the effect has been real. Direct bookings are a growing share of our business every year, because we own those relationships and we own the website they come through.

The End Goal

Vendors change. Software companies get acquired. The website platform you rely on today might not exist in five years, or it might get expensive enough that the math stops working. I have been through that once and do not plan to go through it again.

Your brand, your customers, your data, your email list, your website, your Google rankings. Those should stay with you no matter what happens to any one vendor or platform.

Build more than a portfolio of vacation rentals. Build a vacation rental business you actually own. That means choosing good technology partners, and it means making sure the things that matter most, your website, your audience, your reputation, belong to you.

That is the lesson 100+ doors taught me. I wish I had learned it at 10.

About the Author

Mike Chen is the founder of FunStay Florida, a vacation rental management company with 100+ properties across Central Florida's resort communities, including Orlando, Kissimmee and Davenport. A licensed Florida Realtor and Airbnb Superhost, Mike built FunStay from a single property into a full-service management operation. He wrote this piece as a guest contributor to the HomeRunner blog from Hudson Creative Studio.