If you’ve landed here, chances are you have been searching for the best vacation rental resort near Disney World — and probably came across Windsor Hills Resort and Windsor Island Resort. Aside from sharing the name “Windsor” there is no relationship between the two. And at first glance, they look similar — both offer gated security, a clubhouse, pools, waterslides, and vacation homes with private pools.
If you’re planning a big (and likely expensive!) family vacation, it’s important to dig into real guest experiences and reviews across TripAdvisor, Facebook, and Google. And when you do, a clear pattern emerges:
👉 Windsor Hills is the proven, guest-friendly resort that delivers smooth vacations.
👉 Windsor Island still struggles with its far distance from the major attractions, long gate lines, party noise, and strict towing policies that have frustrated travelers.
Location: 10 Minutes to Disney Vs. 35 or More Minutes.
Windsor Hills is just off US-192 — about 2 miles from Disney’s Animal Kingdom and minutes from the big Welcome To Disney World sign. You can leave after breakfast and still make rope drop. Grocery delivery, restaurants, and stores are all within five minutes. Mid-day theme park break back at your Windsor Hills rental? No problem, it’s easy to do and guests do it all the time!
Windsor Island on the other hand is located a county away, farther south in Davenport. On a map, it’s “only a bit further away,” but once you hit stoplights, school zones, traffic, and construction, it easily turns into 30–60 minutes or more to Disney parking lots and as much as 90 minutes to Universal.
Winner: 🏆 Windsor Hills — close, convenient, and easy. (So close that it actually appears on the Disney World app map!)
Gate & Check-In: Windsor Hills Smooth, Windsor Island… Not So Much.
At Windsor Hills, the 24-hour staffed gate is efficient — they’ve been handling high-volume traffic for almost two decades. Check-ins are quick with a gate and management team that knows how to move cars and guests through with a smile and a “welcome home”.
Windsor Island reviews, though, tell a different story. Guests repeatedly mention massive gate backups — sometimes 30–45 minutes just to enter, especially at peak check-in times. One review even called it “Disney-level lines before you even get to Disney.”
Winner: Windsor Hills — no vacation should start with a traffic jam, and no one should have to wait in a 30 minute line to get home after a day at the parks!
Guest Experiences: Noise, Parties & Towing Headaches.
Because Windsor Island markets itself heavily to large groups, it’s developed a reputation for being party-friendly — not a good thing. Guest reviews have complained about loud music, late-night gatherings, and poor enforcement of quiet hours.
Even worse, Windsor Island’s HOA has adopted aggressive towing policies. Many guests report waking up to find their car gone over minor parking mis-steps — overnight street parking, visitors not properly registered, etc. It’s turned into a recurring theme in online reviews. Waking up to a missing rental car would be a vacation-ender.
Windsor Hills Resort, on the other hand, has carefully developed family-oriented, reasonably managed rules over decades of experience and with an extremely hands-on owner base. The community has strong security, clear parking rules, and a well-balanced mix of families and return visitors who respect the resort vibe. In other words, more of a “welcome home” feel!
Winner: Windsor Hills — peaceful, predictable, and guest-friendly.
Amenities: Reliability Beats “New” Factor
Both resorts have resort-style pools and slides, but Windsor Hills’ facilities are fully established and consistently refurbished. Just grab your wristband at the clubhouse and go!
At Windsor Island, guests have reported sporadic closures and maintenance issues with their pools and water features, in addition to “nickel and diming” for many things guests thought would be included in their stay.
Winner: Windsor Hills — polished and proven.
Guest Reputation: The Power of a Decade of Reviews
Windsor Hills has almost two decades of five-star reviews and repeat guests. Families know what they’re getting, and first-timers feel confident booking.
Windsor Island, on the other hand, is still building its reputation — and early feedback clearly shows that. Between gate line chaos, towing issues, being frustratingly far from the major theme parks, and noise complaints, the honeymoon phase wore off quickly for many visitors.
Winner: Windsor Hills — stability built over time.
Value & Peace of Mind
Nightly rates at both resorts can be comparable in some cases, but in general do tend to skew a touch higher at Windsor Hills — and for good reason. Only one gives you predictable quality and 2 decades of being the vacation rental leader of the Walt Disney World area. Windsor Hills rentals are constantly being updated, with themed kids’ rooms, private pools, and game areas. Windsor Hills owners are known for being responsive, hands-on and very communicative with their guests.
Winner: Windsor Hills — better value, better reviews… and better sleep.
🏁 Final Verdict
When you stack them side-by-side, it’s not even close:
| Category | Winner |
|---|---|
| Distance to Disney | Windsor Hills |
| Gate & Entry | Windsor Hills |
| Noise & Parking Issues | Windsor Hills |
| Guest Reviews | Windsor Hills |
| Value for Families | Windsor Hills |
✨ Choose Windsor Hills for your next Disney trip — where vacations start smoother, stay quieter, and end happier. Don’t gamble on “new and trendy.” Always check reviews online, and go with the trusted favorite that’s been making family vacations magical for over 15 years.