If you’ve ever found yourself lying awake wondering if your vacation rental is worth the effort, you’re not alone.
I’ve been there. I’ve helped dozens of owners in ChampionsGate face that same question: Do I keep managing this property, or is it time to sell?
And let me tell you, there’s no one-size-fits-all answer. But there is a smart path forward — and it starts with getting honest about where you are now and what you actually want next.
Let’s walk through it together.
The Realities of Managing a Vacation Rental in ChampionsGate
When I bought my first short-term rental, I was excited. The photos, the bookings, the income potential — it felt like a dream. But once the messages started rolling in, the AC broke during a guest's stay, and the cleanings got missed... that dream got real, fast.
ChampionsGate is still one of the top-performing short-term rental markets near Disney, but it’s also competitive. Managing a property here means:
Constant guest communication (even at 10 pm)
Staying ahead of pricing and occupancy trends
Coordinating cleanings, maintenance, and supplies
Keeping up with shifting local regulations
For some owners, it becomes a full-time job — and not the passive income stream they imagined. If that’s where you are right now, know this: you're not failing. You’re just hitting the crossroads.
Why Some Owners Decide to Keep Going (and Win Bigger)
Let’s start with the upside. If your ChampionsGate home is in good shape, getting bookings, and bringing in a decent return, there’s a lot to work with.
Here’s when it makes sense to keep managing (with the right support):
✅ You have a solid guest history and 5-star reviews
✅ You’re cash-flow positive and open to investing a bit more in upgrades
✅ You believe in the market and want to hold long-term
✅ You’re just feeling burned out, not checked out
The truth is, some of the best-performing properties I manage through FunStay Homes didn’t start that way. The owners were overwhelmed and ready to throw in the towel.
But after we stepped in, repositioned the listing, adjusted pricing, and implemented local support, those same homes became income machines.
If you’re not ready to sell, that’s okay. Sometimes you just need the right team behind you.
When It Might Be Time to Sell Instead
But what if the numbers just aren’t working? Or you’re over the stress entirely?
Here are signs it might be time to exit:
You’re consistently underbooked despite efforts
Maintenance and guest issues are draining your time or budget
You live out of state, and it’s becoming too much to manage remotely
You want to free up equity to reinvest elsewhere or simplify life
In ChampionsGate, we’re still seeing strong buyer demand — especially from investors looking for turnkey short-term rentals. That means your home might be more valuable than you think, even if the bookings have slowed.
What to Weigh Before You Decide
1. Financial Outlook
Start by asking: How much is your home worth today? What’s your average annual return after expenses? Would selling unlocked capital be possible for you to use elsewhere?
Also, consider whether the home is aging and beginning to require more frequent or expensive repairs. Vacation homes don’t stay maintenance-free forever, and that long-deferred roof or HVAC update could be around the corner.
2. Emotional Readiness
Is this property still something you enjoy owning, or does it feel like a burden? Would letting bring relief or regret?
For some families, the home no longer serves its original purpose — maybe it was once a central gathering spot, but now the kids are grown and visits are fewer and farther between.
If the vacation home has started to feel more like an obligation than a retreat, that may signal it's time to reevaluate.
3. Market Trends
ChampionsGate remains a high-demand vacation market, but new developments and shifting regulations mean timing matters if you’re thinking about selling; doing so before inventory increases could help you stand out.
Not Ready to Sell? You’re Not Out of Options
This is where I step in—not just as a Realtor but also as the co-founder of FunStay Homes.
I started FunStay with a close friend because we were frustrated with property managers who didn’t treat our vacation rentals like real businesses. We wanted to create a solution that not only took care of the day-to-day but helped maximize returns, bookings, and guest satisfaction — and that’s what we’ve done.
Today, FunStay managesover 100 vacation homes across top Central Florida destinations, including ChampionsGate.
If you want to keep your rental income flowing but don’t have the time — or don’t live nearby — our local team has your back.
We’ll:
Add your property to Airbnb, VRBO, Booking.com, and our own growing direct booking site, FunStayHomes.com
Handle guest messages, cleanings, repairs, and dynamic pricing
Help your property shine online — and in real life
Whether you’re holding for a few more years or just need a break, FunStay gives you the freedom to keep earning without being on call.
Through FunStay Homes, I offer full-service vacation rental management specifically for ChampionsGate and other top Central Florida markets. Whether you're nearby or across the country, we help:
Handle bookings, pricing, and guest communication
Coordinate cleanings and on-the-ground support
Refresh your listing and drive more visibility
Maximize your income — without the overwhelm
You don’t have to sell to regain peace of mind. Sometimes, you just need a partner.
But If You Do Want to Sell, Here’s How to Do It Right
I don’t just manage vacation rentals — I help clients sell them too.
If you’re leaning toward listing, I’ll guide you through:
A realistic home valuation based on current STR performance
Pre-listing prep to appeal to both homeowners and investors
Professional marketing and buyer targeting strategies
Selling a vacation home isn’t like selling a primary residence. You need someone who understands short-term rental value, income potential, and how to market that to the right buyers. As a Realtor and STR investor, that’s exactly what I do.
My Take? There’s No Wrong Move — Only Smart Timing
I’ve seen ChampionsGate homeowners double their ROI by holding, and I’ve seen others walk away with six-figure equity gains through a well-timed sale.
What matters is your goals.
Are you trying to scale? Simplify? Get your time back? There’s no shame in either choice. But making the right call starts with understanding your numbers, your energy, and your long game.
Let’s Talk — No Pressure, Just Perspective
If you’re wondering whether to keep managing or finally sell, let’s chat. I’ll give you honest advice based on your property, your numbers, and what I’d do if I were in your shoes.
You don’t have to do this alone, and you don’t have to rush. Let’s figure out the next best move for your ChampionsGate vacation home.
Frequently Asked Questions
Yes! In fact, many investors are looking for turnkey STRs. I help sellers transfer listings and guest history to new owners smoothly.
That depends on your long-term goals and how underperforming it is. Sometimes a management change can fix it. Other times, selling is the smarter move.
I offer a free home valuation that factors in local comps and STR performance, not just traditional resale value.
It depends on your home’s condition, current rental performance, and market timing. I can run the numbers on both scenarios so you can make a smart, informed choice.
Absolutely. Most of my clients are out of state. We’ll handle everything from staging to showings or STR turnovers.
No problem. Whether you want to sell this year or not at all, I’m here to give honest insight and help you make the best move for your future.
