
Villa holiday rentals in Windsor Hills
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Top-rated villa rentals in Windsor Hills
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Family Dream Vacation Villa w 6br + pool & Resort
The perfect family vacation destination! Champions Gate is just outside Orlando and a quick drive to Disney and other theme parks. Want to enjoy the Florida sunshine without having to leave the neighborhood? Enjoy your own private pool or take a walk to the Oasis Clubhouse or 2nd clubhouse where you can enjoy amazing resort amenities for free! Villa Features: Pool/Spa, GameRoom, VideoGames, Baby friendly. Clubhouses: Pools, Slides, LazyRiver, SplashPad, Gym, Restaurant, Bar, Tennis, Volleyball

150 Inch 4K Movie Theater Pool & Spa sleeps 16
"Just 3 miles from Disney up to 16 guests! Unwind in the pool & jacuzzi. A private cutting-edge Movie Theater, featuring a 150-inch screen, 4K projector, and immersive surround sound. Relive your favorite movie moments like never before! Stream on Roku, game on PS5, and enjoy high-speed Wi-Fi for endless fun. The well-equipped kitchen is perfect for large families and with 6 bedrooms and 4 en-suite baths, privacy is guaranteed. A Star Wars and a Disney-themed rooms so the kids will feel at home.

Luxurious Pool Villa, Minutes From Disney World
Enjoy the big private pool after a long day at the themes park with family. Sun bath in a spacious pool deck all day or get a back massage by our spa. The villa had a gentle light system combined with the main cold color tone to create a feeling of comfort and relaxation. Your kids will love the Mickey twin beds and the game room very much. Our villa located within 5-15minutes of majors shopping center/outlets, restaurants, bars, water park, and themes park. We had everything, just missing you!

*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!

*Private Resort Oasis: Golf-Front, Pool/Spa/Cinema
The perfect balance of STYLISH DESIGN, LUXURIOUS COMFORT, & ENDLESS ENTERTAINMENT, beautifully situated with stunning views in the sprawling 3.5 square mile Reunion Resort. You will have your own private pool, spillover spa, STAR WARS cinema-game room with pinball, classic arcade games, and karaoke, MARVEL kids room with tube slide and double bunks, the latest Xbox Series S, a sprawling 2000 ft2 pool deck, fire pit, and even a HARRY POTTER cupboard hidden under the stairs, minutes to Disney.

3mi to Disney Star Wars Galaxy Edge 7BDRM Villa
Embark on a galactic adventure in our Star Wars-themed 7-bedroom, 4.5-bathroom villa just 3 miles to Disney. Close to Celebration, Old Town & downtown Orlando, this retreat features a fully equipped kitchen, private pool & patio. Each room transports you to iconic Star Wars locations like Tatooine, Mos Eisley Cantina, Jabba's Palace, Dagobah, Death Star, Coruscant, Millennium Falcon & Bespin. The community offers resort amenities including pools, trails, gym, mini golf, tennis & basketball.

Sunny Family Retreat ~ Peaceful Pool ~ Game Room
Unwind in this sunny 4 Bedroom 3 Bath house nestled in a serene family-friendly neighborhood. This prime location allows quick access to nearby restaurants and shops while being just a short drive away from Disney World, Universal, Legoland, and more. The lively pool deck and entertaining game room offer various relaxing and fun amenities. ✔ 4 Comfortable Bedrooms ✔ 3 Large Bathrooms ✔ Fully Equipped Kitchen ✔ Swimming Pool ✔ Game Room ✔ Six TVs w/ Roku ✔ Sun Loungers Learn more below!

8 BR Villa, Private Pool, Theater, Min to Disney!
Big and Beautiful Themed Vacation Villa in premium gated Encore Resort. Spacious main floor for entertaining large groups - bring the family and friends! Enjoy the included resort amenities a minute's walk from the front door. Or, relax around your private pool and custom summer kitchen. Enjoy big-screen movies and sound in the theater in premium loungers, and play classic arcade games! 10-15 min from Disney, one of the closest villa resorts. Tons of shopping and dining nearby!

5BR Family Vacation Villa w/Free Pool Heat
Professional Hosts & Guest Favorite Home! Immaculate and well equipped Stargazer Villas vacation home at Windsor Island Resort now featuring Pickleball Court! This central Florida villa has heated pool included for your family to relax in after a busy day at the parks. Family friendly, featuring Star Wars, Harry Potter, & Encanto themed bedrooms, and a new Mario World game room! Stargazer Villas provides the perfect place to create unforgettable memories with your family.

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

4mi to Disney | Games | Private Pool
Get ready to make memories of a lifetime just over 3 miles to Disney when you stay at this newly renovated Star Wars and Lego-themed private pool villa. Located in Formosa Gardens Estates, a prestigious gated community, our home is professionally furnished with multigenerational families in mind and can comfortably sleep up to 15 guests. After a trip to the parks, enjoy a refreshing dip in the private pool and rest those tired feet in the spa (pool heat included!).

Pet Friendly Villa*Private Pool + Spa*Near Disney
✨ Looking for comfort, privacy, and fun near Disney? Our pet-friendly home is ready to welcome your family — including your furry friend — for amazing days under the Florida sun. Magic Kings House invites you to create magical moments with your loved ones, offering comfort and exclusivity at Windsor Palms, the resort most loved by guests. Every detail has been carefully prepared to make your vacation easy, relaxing, and filled with wonderful memories. 🌴🐶☀️
Popular amenities for villa rentals in Windsor Hills
Private villa rentals

Casita Kissimmee!Family Vacation Villa! 8minDisney

Funtastic Villa 6br4ba,pool, sleeps 14-Near Disney

Lakefront Private Pool Villa, 10min to Disney

Luxury Villa! /Game Room/ Pool Heater

South facing Modern villa in quiet gated estate

The Balmoral Manor: Luxurious & Bright 5BR Oasis

Pool Movies|Water Park|Movie Theater|Arcade|Themed

The Manatee Manor | 5 BR•Windsor Hills•Game Room
Luxury villa rentals

Blue Paradise 15BR 11BA, Sleeps 36, Theater/GameRm

Pickleball PoolsideMovies |WalkToWaterpark| Arcade

15min2parks! 9B, Pool/Spa/Theater/Karaoke/Vgames

Magical Disney House-Pool & Hot Tub,Free Waterpark

The Golden Bear Villa | Private Pool & Theater

NEW Unique 6BR,private pool,Full game room, + MORE

Epic Disney Villa • Hidden Arcade & Playroom!

Sleeps 24✦Free Pool Heat✦15 min to Disney✦Hot Tub
Villa rentals with a pool

7BR Disney Villa Escape Room+ Pool +Cinema+Game Rm

PlutosPad Villa

4 Suites Villa near Disney+ Hot Tub@ Magic Village

Luxury 4 Bedrooms, 3.5 Bathrooms with pool.

Amazing home 5 mins to Disney Orlando

Palm Villa | 6BR Disney Retreat + Heated Pool/Spa

Luxury 4BR Retreat | Pool & Spa + Game Room

WaterView 4 miles to Disney 3Br 2Ba Pool Home
When is the best time to visit Windsor Hills?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ₹20,467 | ₹20,028 | ₹22,224 | ₹23,278 | ₹20,380 | ₹20,292 | ₹22,927 | ₹20,643 | ₹19,062 | ₹20,204 | ₹20,643 | ₹22,927 |
| 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 villa rentals in Windsor Hills

Total holiday rentals
Explore 150 holiday rentals in Windsor Hills

Nightly prices starting at
Windsor Hills holiday rentals start at ₹8,784 per night before taxes and fees

Verified guest reviews
Over 3,000 verified reviews to help you choose

Family-friendly holiday rentals
140 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Holiday rentals with a pool
140 properties feature pools

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wifi availability
120 of Windsor Hills holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Windsor Hills rentals

4.8 Average rating
Windsor Hills stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Rentals with a washing machine and dryer Windsor Hills
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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Universal's Volcano Bay
- SeaWorld Orlando
- Disney Springs
- Discovery Cove
- Old Town Kissimmee
- Disney's Animal Kingdom Theme Park
- Magic Kingdom Park
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Reunion Resort Golf Courses - Palmer & Watson
- Walt Disney World Resort Golf
- Aquatica
- Island H2O Water Park
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- Kissimmee Lakefront Park
- Universal's Islands of Adventure
- Ventura Country Club