
Villa vacation 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.

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!

Near Disney Gated LakeView Pvt Heated Pool
Lowest Cleaning fee! Free pool heating Oct 17-19! Military discnts. New Sofa, Dolby Home theatre, wall mnt 65" LED TV w/ Airplay. Dedicated Remote office. Sunset Lakes is a secure gated comnty ~12 min from Disney & other parks. Villa offers Lake View pvt pool, gorgeous sunset, Playroom, Fishing Rod/dock. Fully furnished & sparkling clean w/ 5 beds - 1 King, 2 Queens, 2 Twin beds with 3 baths, kitchen & laundry. Come & enjoy your next trip to Disney & leave everything to a fantastic experience!

❤NEW Gorgeous 5br/3.5ba|POOL| Game ROOM| Disney
Nestled in the peaceful 4 Corners community close to Disney & top rated attractions, Target, Publix & restaurants. Newly updated, inviting and modern 2 level, 5 bedroom/3.5 bath with comfortable luxurious beds! Equipped with a private pool (heat for an extra fee), game room, BBQ grill & free Nespresso. Out back is a mini golf putting green, corn hole and fire pit for the family to gather around under the warm vibe of string lights. A place for the family to retreat, relax, reset and have fun!

*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.

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!

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!

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!

Top Resort PoolHome Free Amenities 4 Miles2 Disney
Step into your own beachy paradise! Just 4 miles from Disney, this 4BR/3BA Florida villa is a masterpiece of beauty and comfort. Picture yourself enjoying the resort-style pool, beach volleyball, tiki bar, and more. Your private pool and game room add an extra touch of luxury. Don't miss out on the ultimate getaway—book now and let the magic unfold! Your dream escape is just a click away. Seize the moment and secure your reservation for an unforgettable experience in this tropical haven!

Beautiful 4 Bedroom Pool Villa Near Disney World
This sunny single story home has 4 beautiful bedrooms (2 master suites) and 3 full bathrooms with its own private screened pool. It is an ideal accommodation for 2 families to share, or one large family. This villa is located in the gated community, a small peaceful community set away from any main road traffic. The home is situated approximately 15 minutes from the Walt Disney World, and is conveniently located from all major Orlando attractions, nearby restaurants and shopping.

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 Windsor Hills villa rentals
Private villa rentals

Casita Kissimmee!Family Vacation Villa! 8minDisney

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

PlutosPad Villa

Luxury 4 Bedrooms, 3.5 Bathrooms with pool.

Lakefront Private Pool Villa, 10min to Disney

Fabulous 4 bed South facing Lake view near Disney

25%off/Close to Disney/Hot Tub/Private Pool/Fenced

The Balmoral Manor: Luxurious & Bright 5BR Oasis
Luxury villa rentals

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

3mi to Disney Star Wars Galaxy Edge 7BDRM Villa

Pickleball PoolsideMovies |WalkToWaterpark| Arcade

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

The Golden Bear Villa | Private Pool & Theater

"Disney Serenity": Luxe 8BR Villa/ Privacy/ Pool

Sleeps 24✦Free Pool Heat✦15 min to Disney✦Hot Tub

9BR Epic Memory Making Villa with Free Pool Heat!
Villa rentals with a pool

Free Pool Heat & BBQ|Disney Nearby|Resort|Waffles

The Keys Villa

Disc rate Spacious View4bdrm SplashPool & Yoga Rm

Amazing home 5 mins to Disney Orlando

Private Family Villa w/ Pool, Game Room, Resort

Mickey’s Backyard 6Bedroom Villa Resort- BBQ&Pool

Stunning spacious Villa/Ext S/W Facing Pool Deck

*Pet Friendly* Free Pool Heat - 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 | ﺩ.ﺇ856 | ﺩ.ﺇ837 | ﺩ.ﺇ929 | ﺩ.ﺇ973 | ﺩ.ﺇ852 | ﺩ.ﺇ848 | ﺩ.ﺇ959 | ﺩ.ﺇ863 | ﺩ.ﺇ797 | ﺩ.ﺇ845 | ﺩ.ﺇ863 | ﺩ.ﺇ959 |
| 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 vacation rentals
Explore 150 vacation rentals in Windsor Hills

Nightly prices starting at
Windsor Hills vacation rentals start at ﺩ.ﺇ367 per night before taxes and fees

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

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

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Vacation rentals with a pool
140 properties feature pools

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wi-Fi availability
120 of Windsor Hills vacation rentals include wi-fi 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!
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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
- Universal's Islands of Adventure
- Kissimmee Lakefront Park
- Ventura Country Club
- Shingle Creek Golf Club