
Villa holiday rentals in Windsor Hills
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Top-rated villa rentals in Windsor Hills
Guests agree: these villas are highly rated for location, cleanliness and more.

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 Golf-Front Oasis with 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.

Disney Dream Villa- 10 Minutes From Disney!
Get ready for the home of your dreams! Disney Villa is a spacious 5 bedroom, 3.5 bathroom home that is inspired by the magic of Disney, and is about 10 minutes from the parks! This home sleeps a whopping 10 people, perfect for large families! The home also has a living room, dining room, full kitchen, a game room, laundry area, and a private pool and lanai area. Guests have access to Windsor Palms' many on-site amenities. If you're looking to be close to the magic, this is the home for you!

Feel the Magic 9 min Disney, Pool & Pet friendly
⨠Looking for comfort, privacy, and fun near Disney? Our home features a private pool and spa, perfect for relaxing after the parks. Optional pool heating is available for $49 per night. Thoughtfully prepared for families, the house welcomes guests, including those traveling with pets, for easy Florida days. Magic Kings House invites you to create unforgettable moments at Windsor Palms, a favorite resort among guests. Every detail has been carefully arranged to provide a memorable stay.

8Bd 4K Movie Theater 155 Inch Screen Pool & Spa
A vacation home that takes your entertainment seriously! Thatâs our 8-bedroom villa in Emerald Island Resort at 3 miles from Disney⌠Ready to enjoy themed bedrooms, a premium private movie theater with a 155-inch screen, 4K projector, 5.1 surround sound, and a PS5 for gaming? Relive your favorite films in stunning quality, just like in the best movie theaters. Private Pool and Spa will make your vacation unforgettable! Weâre ready for families and groups, to offer fun, comfort, and luxury.

Mad Men Magic Kingdom House*FAB POOL*OutdoorMOVIE
AMAZING Pool Deck Extension cira 2023! Its the BIGGEST pool deck at the resort! Plus JAW DROPPING, Fancy, Fun, Fountain Jets w/ LED lighting, high-end glass tile & a Mickey Mosaic giving you an ULTIMATE luxury pool experience. This SALT WATER POOL/SPA will leave your skin feeling soft w/ no eye-sting & it has botanical qualities for your muscles after long days at the parks! Enjoy all this plus our unique OUTDOOR MOVIE EXPERIENCE & FIRE-PIT for the BEST vacay ever only 6 miles to Disney!

Cozy Themed Villa 6 BR | Close to Disney
đď¸âď¸đââď¸Stay just minutes from Disney in this spacious 6-bedroom home, perfect for a family getaway. It comfortably sleeps up to 14 guests and is designed for both kids and adults to enjoy. Located in Windsor Hills Resort â one of the closest communities to Disney World â youâll have quick and easy access to the parks. Enjoy themed bedrooms, a game room, and your own private patio and pool â great for relaxing after a fun day at Disney.đ´đđŠłđĽ˝đŠ´ â¤ď¸â¤ď¸We'd love to welcome you here!

Luxury Villa! /Game Room/ Pool Heater
Luxury Villa on a gated community in Kissimmee (Four Corners). Modern. Situated 10 min. from Disney theme parks. Well decorated and presented. Game Room, Mini Gym, Beautiful, large pool deck which is totally enclosed and secluded. There is a private Pool and Spa. Three Bedrooms and Bedroom one is separate from the main house but still enclosed in the building. This would be ideal for a young couple within the group as it has its own bathroom, small kitchen and also total privacy.

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! min from Disney, one of the closest villa resorts. Tons of shopping and dining nearby!

Zen Inspired Villa near Disney
A haven of tranquility. Here simplicity meets elegance in a minimalist design that integrates natural materials. Large spaces with abundant natural light that invite you to relax. Comfortable furniture and comfortable sheets. We have taken care of every detail to offer you a complete experience, from yoga/meditation mats, books and games for the little ones in the house to board games to share with the family. A private pool with a great view and lights complete the place.

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
Popular amenities for villa rentals in Windsor Hills
Private villa rentals

BEST HOUSE! Potter, CARS, Princesses, StarWars

Casita Kissimmee!Family Vacation Villa! 8minDisney

WHR Private 4 bd Villa, Gameroom/Pool/Spa, Disney!

Luxury Townhouse Near Disney | 3BR

Fabulous 4 bed South facing Lake view near Disney

Villa w/ Pool, Game Room, Hot Tub, Near Disney!

Remodeled Windsor Hills Villa w/ Pool & Game Room

Magical 5BR Themed Pool home + Game Room!
Luxury villa rentals

Storey Lake 10BR Villa Near Disney, Pool Waterpark

3mi to Disney Star Wars Galaxy Edge 7BDRM Villa

Supervilla at Championsgate | Waterpark | Themed

15min2parks/Lakeview/Vgames/Karaoke/Movie Rm/Pool

The Golden Bear Villa | Private Pool & Theater

Free Pool Heat! Disney Themes, Arcade, Sleeps 22

Epic Disney Villa ⢠Hidden Arcade & Playroom!

Brand New 9Bd Mansion Pool/ Spa At Windsor Island
Villa rentals with a pool

Amazing pool house - 10 MIN FROM DISNEY ORLANDO

4 Suites Villa near Disney+ Hot Tub@ Magic Village

Lakeview Villa| Heated Pool, BBQ & Near Disney

Mickey's Backyard Themed 6BR with Pool

The Balmoral Manor: Luxurious & Bright 5BR Oasis

The Manatee Manor | 5 BRâ˘Windsor Hillsâ˘Game Room

Luxury Villa | Pool, Spa, Game Room | Near Disney

Storybook Stay + Epic Outdoor Space - 7BR 4 Kings
When is the best time to visit Windsor Hills?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ÂŁ178 | ÂŁ186 | ÂŁ193 | ÂŁ194 | ÂŁ170 | ÂŁ169 | ÂŁ187 | ÂŁ167 | ÂŁ147 | ÂŁ164 | ÂŁ180 | ÂŁ211 |
| 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 140 holiday rentals in Windsor Hills

Nightly prices starting at
Windsor Hills holiday rentals start at ÂŁ81 per night before taxes and fees

Verified guest reviews
Over 3,180 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
130 properties feature pools

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
140 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 â averaging 4.8 out of 5!
Destinations to explore
- Pet-friendly rentals Windsor Hills
- Family-friendly rentals Windsor Hills
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- Rentals with a washing machine and dryer Windsor Hills
- House rentals Windsor Hills
- Apartment rentals Windsor Hills
- Rentals with a patio Windsor Hills
- Rentals with pools Windsor Hills
- Rentals with outdoor seating Windsor Hills
- Fitness-friendly rentals Windsor Hills
- Rentals with a cinema Windsor Hills
- Flat rentals Windsor Hills
- Rentals with a hot tub Windsor Hills
- Rentals with an EV charger Windsor Hills
- Villa rentals Four Corners
- Villa rentals Osceola County
- Villa rentals Florida
- Villa rentals United States
- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Orange County Convention Center
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Magic Kingdom Park
- Orlando / Kissimmee KOA
- Discovery Cove
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Southern Dunes Golf and Country Club
- University of Central Florida
- ChampionsGate Golf Club





