
Vacation rentals in Windsor Hills
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Top-rated vacation rentals in Windsor Hills
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Game & Theater Room, Castle Bunks, Pool & Spa
Vacation at Windsor’s Best located in Windsor Hills Resort just 2 miles from Walt Disney World. This one-story 4 bed, 4 bath vacation villa has everything you need for a wonderful getaway with family or friends. Situated on an elevated corner lot, this spacious villa with it's private pool and spillover spa offers a beautiful view overlooking the resort community. Plus, guests have access to the family-friendly Windsor Hills Resort amenities, including the water park, playgrounds, gym and more.

Disney Escape at Windsor Hills
This is a fantastic family vacation townhouse located just four miles from Walt Disney World! Inside, you'll find a full kitchen with a breakfast bar, a dining table for six, and a living area with a TV for streaming all your favorite channels! Right outside, take a refreshing swim in your private pool. Guests will be able to enjoy a wide variety of resort-style amenities close by including a community clubhouse with a game room, Olympic-size pool, children's waterpark, putting green, and more!

5 miles to Disney- Private Pool - Arcade Games
Just 4 miles from Disney, our luxury townhome is your family’s perfect escape! With a private splash pool, brand-new 65” Smart TV, and family-friendly gear (stroller, pack n’ play, high chair), you’ll have everything needed for a carefree stay. Located across from Windsor Hills Resort’s clubhouse, enjoy resort perks like a pool, splash pad, fitness center, and theater! Sleeps 8 comfortably with 3 en-suite bedrooms, including a themed Disney beach kids’ room. Fun, comfort, and convenience await!

*Brand New!* Minutes to Disney + Free Resort!
Closest FREE resort to Disney Parks! Hibiscus Hideaway is a 6 bedroom 4 bathroom luxury villa that sleeps 14. Completely renovated in October 2022! * Kitchen is loaded & all baby gear provided. * Custom game room with A/C, LED panel lighting & ROCK CLIMBING WALL! * New Roku smart TVs & NEST tech throughout. * Outdoor space includes your own private pool, hot tub, overhead lighting, NEW BBQ grill & 10' custom-built farmhouse table to seat the whole family! Every detail has been thought of!

Toy Story Retreat Near Disney in Windsor Hills
Experience the magic of Disney at your very own “Toy Story Retreat.” - 3 bedrooms and 2 bathrooms with Disney-inspired design - Family-friendly atmosphere in a newly remodeled condo - Full access to Windsor Hills Clubhouse amenities - Ground-floor unit with greenspace views - Free WiFi and basic cable included - Just minutes from Walt Disney World® Resort It's important that the title is as close to 50 characters. You should use some of the other characteristics of the listing.

🏖 Resort Condo | 🎢 2mi -> Disney | 💦 Waterpark Fun
Welcome to Mickasita @ Windsor Hill's! Our condo is the ideal family vacation spot, conveniently located just minutes away from Disney World and all your desired attractions. During your stay, our whole-condo dehumidifier will maintain a comfortable and healthy level of humidity. Recently upgraded, our condo is sparkling clean and offers many resort amenities with the convenience of a home. You'll find new beds with fresh linens, flat-screen TVs, high-speed internet, a gym, and more.

Mr. Clean's Cozy Disney Home w/ Luxury Finishes
• Newest house in the #1 resort community in the Disney Area, Windsor Hills • ALL Mattresses & Pillows are encased in waterproof SANITIZED covers. • 2 FUN children themed rooms (Star Wars, & Frozen) • Onsite, driveway parking for 3 vehicles • FREE pool heat + BBQ with ALL rentals • Fully equipped + stocked kitchen; including Keurig machine • Self check-in with digital lock • Super FAST Wi-Fi wireless internet speed at +1,000 Mbps!! • Property is managed directly by owner

Windsor Orlando Private Arcades,Theater,Pool-Spa
Orlando, Disney, Arcade, Movie Theater, Massage Chair, Pool, Hot Tub, 2 King Beds, Kids Bunk Bed, Kissimmee. Upgraded games room IN the private home, theater for evenings home and your private lanai with pool and hot tub. Choose from including Pump It Up dance, Sponge Bob Racing, NASCAR racing, Legends 3, Pac-Man's Arcade Party, an 80-inch TV, and an Xbox 360. Watch your favorite movies on the 92-Inch projection screen, surround sound, and stadium style seating.

2584 - 6 Bedroom w/ Pool and Water Park Included
Welcome to Your Ultimate Vacation Escape at Windsor Hills Resort! This charming vacation home in Windsor Hills Resort offers six spacious bedrooms and is perfect for the entire family. Located in one of the finest gated communities in the area, Windsor Hills Resort features 24-hour security, ensuring only permitted guests have access to the neighborhood. We’re just a short distance from Disney parks, shopping, dining, and many of Orlando’s top attractions.

Disney fireworks new house - 5 minutes to Disney
Welcome to our beautifully decorated 2-store Townhouse only 6 miles away from the Disney Parks and many other attractions. You will have the entirely house for yourself and your family while enjoying your vacation in Florida. We have sought to equip our home to a high standard and to anticipate your needs for a luxurious stay. We truly believe that our home is special based on 4 main reasons: Location, Security, Decoration and Comfort.

DISNEY, WATER park, Private POOL, Comfort by A3G
Your dream getaway, starts In this 3beds 3 baths vacation home away from home! With private pool, Located in the amazing 5 stars resort at WINDSOR HILLS, only 3 miles away from all the wonders and magic of Disney. For Endless entertainment just walk to the Clubhouse and encounter the beautiful typhoon style pool, jacuzzi, brand new water park, arcade, fitness center, volleyball and basquetbol courts, kids playground and much more

Lovely vacation condo close to Disney & Universal!
Family friendly 3 bedroom 2 bath condo on first level (handicap accessible) at Windsor Hills Resort. Gated access with private parking. Go straight to the condo with Lockbox access code. 7 minute drive to all Disney parks. As a guest you have access to the beautiful pool, hot tub, Water Park, gym, movie theater, Community Center at no extra cost. Everything is open and available.
Popular amenities for Windsor Hills, Four Corners vacation rentals
Stay near Windsor Hills's top sights
Windsor Hills, Four Corners home rentals

4 bedroom, south facing pool 3 miles to Disney

Paradise Cove at Windsor Hills Resorts

10 min to Disney| Themed | Sauna | Pool | Golf Sim

Themed villa wt Pvt Pool near Disney|Gameroom, BBQ

Windsor Hills Resort Home Disney Free Pool Heat

4 minutes to Disney - Sleeps 14, Arcade, Pool

ReDesigned | Windsor Hills | Location | Water Park

Fantastic home just 3 miles from Disney World!
Other great vacation rentals in Windsor Hills

Windsor Hills Resort| 8 min to Disney| Priv Pool

free waterpark-2 king suites-minutes to parks

Disney Pool Villa | Windsor Hills | Sleeps 8

Luxury Mickey Themed Townhome in Windsor Hills Res

Themed Family Pool Home 10 Min to Disney Game Room

Once upon a galaxy: Star Wars/fairytale retreat

Your Sun, Fun and Everything Relaxation Retreat!

Luxurious home 2 miles from Disney - Windsor Hills
When is the best time to visit Windsor Hills?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$47,490 GYD | G$48,536 GYD | G$52,093 GYD | G$52,302 GYD | G$46,863 GYD | G$48,327 GYD | G$51,256 GYD | G$46,863 GYD | G$42,469 GYD | G$47,281 GYD | G$49,164 GYD | G$52,511 GYD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Quick stats about vacation rentals in Windsor Hills

Total vacation rentals
Explore 680 vacation rentals in Windsor Hills

Nightly prices starting at
Windsor Hills vacation rentals start at G$10,460 GYD per night before taxes and fees

Verified guest reviews
Over 13,040 verified reviews to help you choose

Family-friendly vacation rentals
620 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Vacation rentals with a pool
670 properties feature pools

Rentals with dedicated workspaces
400 properties have a dedicated workspace

Wi-Fi availability
650 of Windsor Hills vacation rentals include wi-fi access

Popular amenities for guests
Guests love Self check-in, Gym, and BBQ grill across Windsor Hills rentals

4.7 Average rating
Windsor Hills stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Fitness-friendly rentals Windsor Hills
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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Walt Disney World Resort Golf
- Magic Kingdom Park
- Disney's Animal Kingdom Theme Park
- Old Town
- Epcot
- ESPN Wide World of Sports
- Kia Center
- Reunion Resort Golf Courses - Palmer & Watson
- Universal's Volcano Bay
- Discovery Cove
- Aquatica
- Island H2O Water Park
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- Universal's Islands of Adventure
- Ventura Country Club
- Shingle Creek Golf Club




