Windsor Cay looks like a dream; it has brand-new homes near Disney, and short-term rentals have been approved. But buying here without a plan is how smart people lose money fast.
From overestimating rental income to underestimating setup costs, the most common mistakes aren’t obvious until it’s too late.
This guide breaks down the 10 biggest mistakes buyers make when investing in Windsor Cay Resort and how to avoid falling into the same traps. If you want real ROI, not just real estate, start here.
1. Buying Without Understanding the Local Short-Term Rental Market
Most people make big mistakes when buying a vacation home because they assume all short-term rental (STR) zones work the same. But just because a community allows vacation rentals doesn’t mean your investment will perform the way you expect.
In Windsor Cay Resort, success depends on more than just location. Yes, it’s minutes from Disney, but performance hinges on things like:
- Seasonal demand patterns (summer vs. off-season)
- School break travel peaks
- Local competition from nearby resorts (like ChampionsGate and Solterra)
- Your ability to price competitively and stay visible on platforms like Airbnb and VRBO
One of the biggest Windsor Cay investment risks is buying purely based on emotion, like falling in love with a model home or amenities, without running the numbers. A stunning vacation home doesn’t automatically equal high occupancy or profit.
2. Underestimating Setup Costs After Closing
Let’s get this straight: the price you see on the builder’s brochure is not the total cost of owning an Airbnb-ready home. One of the most expensive Windsor Cay investment risks? Thinking you’re done after closing.
You’re not.
The house is just the beginning.
Windsor Cay homes are delivered completely unfurnished. That means:
- No beds
- No dining tables
- No curtains
- No silverware
- Not even toilet paper holders
If you plan to turn your new property into a high-performing short-term rental, your vacation rental setup needs to include:
- Quality mattresses and blackout curtains (guests care)
- Full kitchen supplies down to the wine opener
- Smart TVs in every room
- A reliable Wi-Fi setup (yes, people will leave bad reviews over this)
- Pool safety features, smart locks, noise monitoring, and other essentials
And don’t forget: professional photography, a designer who understands Airbnb property prep, and time to get everything delivered, assembled, and guest-ready.
3. Assuming Every Floor Plan Performs the Same on Airbnb
Just because two homes have 8 bedrooms doesn’t mean they’ll bring in the same income. That’s a rookie assumption that kills Airbnb’s ROI faster than you’d think.
Yes, Windsor Cay offers multiple floor plans with similar square footage and bedroom count. But here’s what most buyers don’t realize:
- Layout matters. Guests prefer open kitchens, larger common areas, and at least two living spaces (especially for big groups).
- Bedroom configuration matters. Think: king beds for adults, bunk rooms for kids, and no sofa beds unless you want guest complaints.
- Orientation matters. South-facing pools rent better. Homes with rear privacy (no back-to-back neighbors) perform better, too.
- Distance from the clubhouse matters. Too close? You get noise. Too far? Guests might skip amenities altogether.
Even your photos make a difference. Two identical homes, one professionally styled and shot, the other not, will earn completely different booking rates.
4. Overlooking HOA, CDD, and Ongoing Costs
One of the biggest mistakes when buying a vacation home is ignoring the fine print, specifically the recurring costs that hit you every single month, whether your property is booked or not.
In Windsor Cay, you’ll be paying both HOA and CDD fees, and they’re not pocket change. Add in utilities, pool service, pest control, lawn care, internet, and insurance, and suddenly your “passive income property” is bleeding cash during the low season.
The truth is, neglecting long-term maintenance costs and community fees is how investors end up stressed, not successful. If you don’t factor these in from day one, the numbers will eat you alive later.
5. Skipping Professional Design for Your Airbnb Listing
Here’s the cold truth: guests scroll past boring. If your listing looks like it was furnished in a rush with whatever was on sale at IKEA that week, don’t be surprised when your calendar stays empty.
This is one of the most overlooked and most expensive mistakes buyers make. They spend $700K on a Windsor Cay home, then cheap out on the interiors. Big mistake.
In a market flooded with themed rentals near Disney, your place has to pop. Think bold statement walls, themed kids’ rooms, Instagrammable details, and lighting that flatters every photo.
Homes with great vacation rental appeal get booked first and at higher rates. Period.
Want the best bookings? Follow solid Airbnb design tips: hire a stylist who knows the STR market, stage with intention, and invest in a professional photographer. You’re not furnishing for comfort—you’re furnishing for clicks, saves, and shares.
Because the average doesn’t sell on Airbnb. But memorable? Memorable prints money.
6. Thinking You Can Self-Manage Remotely Without Systems
So you think you’ll just “try managing it yourself” from across the country?
Self-managing sounds doable until it isn’t. Most first-time investors don’t realize that short-term rental management is 24/7. Not 9–5. Not whenever-you-feel-like-it.
Windsor Cay guests expect hotel-level service. If you can’t deliver it fast, they will leave a bad review that tanks your future bookings.
Hiring a local, full-service property manager may seem like a cost, but it’s actually protection for your time, your sanity, and your ROI.
Want true passive income? Systematize or outsource. Anything less is just gambling with your reputation.
7. Not Asking the Right Questions About Pulte’s Build Process
Here’s one of the sneakiest mistakes when buying a vacation home: trusting the builder knows what’s best for your investment. Spoiler alert, they don’t.
Pulte Homes builds beautiful properties in Windsor Cay. No doubt. But they’re not your investment advisor, and they’re definitely not your Airbnb strategist.
If you don’t ask the right questions about what’s included, what costs extra, when delays might happen, or how walkthroughs are handled, you’re walking in blind.
This is where experienced Pulte buyer advice comes in handy. Because once your contract is signed, you’re in their system, and it moves fast.
Ask now, or pay later. Those are your two choices.
8. Overestimating Rental Income Without a Real Strategy
You toured the model, you ran numbers in your head, and you’re feeling confident. Stop right there.
This is where too many buyers shoot themselves in the foot by assuming their Windsor Cay home will magically generate $6,000 a month from day one.
It won’t.
Airbnb income expectations need to be grounded in real data, not dreams. What you earn depends on:
- Reviews (which take time to build)
- Seasonality (you will have slow months)
Listing quality (photos, description, and pricing strategy)
9. Forgetting to Prepare for Exit Strategy
You might think you’re buying this Windsor Cay home “for the long haul,” but plans change.
What if STR laws shift? What if your family stops visiting? What if a recession hits?
A smart exit plan for your vacation home is baked in before you close. Because when the time comes to sell, you’ll be glad you bought a home with options, not one that only worked during one chapter of your life.
10. Not Working with a Realtor Who Specializes in Windsor Cay + STR
Let’s be blunt: the best way to avoid costly mistakes when buying a vacation home is to work with someone who’s actually done this.
Not just someone who sells homes, someone who’s owned them, hosted guests, dealt with reviews, booked calendar gaps, handled leaks, and knows exactly how Windsor Cay works from the Pulte process to Airbnb prep to guest-proofing your rental.
Don’t Let Your Dream Investment Become a Regret
Windsor Cay has big potential, but only if you avoid the costly traps most buyers fall into.
If you’re ready to invest with clarity, confidence, and a strategy that actually works, let’s talk.
I’ll help you make smarter moves before you spend a single dollar too fast.
