
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.

Near Disney Gated LakeView Pvt Heated Pool
LIMITED PROMOTION! FREE CLEANING FOR BOOKING 2 WKS OR MORE! LOWEST CLEANING FEE! Military dscnts. New Pool Heatr, Dolby ATMOS, 65" LED TV w/ Airplay. Remote office setup. Sunset Lakes a secure gated comnty ~12 min from Disney & other parks. Villa offers Lake View pvt pool, gorgeous sunset, Playroom, Fishing dock. Fully furnished, sparkling clean w/ 5 bds - 1 King, 2 Qns, 2 Twin beds w/ 3 baths, kitchen & lndry. Come & enjoy your next trip to Disney & leave everything to a fantastic experience!

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!

Luxury Fun Stay w/Pool/Spa/WaterPark
This stunning 5BR pool home is in the sought-after Champions Gate resort. Just 12 miles to Disney and 19 miles to Universal Studios, it's a short 9-min walk to the clubhouse, offering free access to the lazy river, fitness center, water park, movie theater, and more. With exceptional facilities, the villa comfortably accommodates up to 14 guests, making it perfect for family fun and gatherings. Enjoy a relaxing retreat near top restaurants, attractions, landmarks, and the famous Disney World!

Themed Resort Villa | Pool | Spa | Mins to Disney
The Magic Escape – a luxurious 4-bedroom, 3-bath home in the gated Windsor Palms resort, known for its cleanliness and thematic allure. Just a short drive from Disney World, this retreat has two master suites with en-suite bathrooms, a Mickey Mouse themed bedroom, and a Harry Potter themed bedroom. Enjoy a private, air-conditioned Star Wars movie theater and Marvel game room with shuffleboard and foosball. The private pool and spa, under an enclosed lanai, ensure your privacy and relaxation.

6BR Phenomenal Vacation Home- Free Spa/Pool Heat
Bring the family to this immaculate and well equipped Stargazer Villas vacation home, a guest favorite at Windsor Island Resort, which now features Pickleball! A quick drive to Disney & close to popular attractions, shopping and dining. This immaculately clean villa has a private free heated pool & spa to relax in after a busy day exploring the Orlando area. Family friendly featuring Mickey, Harry Potter, & Avengers themed bedrooms as well as two primary suites and a Star Wars game room!

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

Private South Pool & Nature View | 10m to Disney
Free pool heat! You and your family will absolutely fall in love with this stunning 4 bedroom 3 bathroom pool home backing onto a beautiful forest for complete privacy. The home is centrally located in the wonderful gated community of Sunset Lakes just a short drive from all of Orlando's world famous attractions! Disney World (4.7 miles), Sea World (13.2 miles), Universal Studios Florida, (18 miles). Not to mention dozens of fabulous restaurants within minutes!

Feel the Magic: 9 min Disney • Pool • Pet • Relax
✨ 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. 🌴🐶☀️

House by the Mouse: Something for Everyone!
Welcome to our completely remodeled solar four bedroom, three bath villa, less then four miles to Disney World, and only a short drive to Universal, Sea World, Lego Land, and other local attractions. Designed themed bedrooms include Harry Potter, Mickey and Minnie Mouse, Star Wars, and a romantic master bedroom that allows you to relax in comfort. The pool, spa, and the entire villa is just for you, no need to share with anyone else, so kick back and enjoy!

Luxury Villa in Windsor Hills Resort, 2 miles / 5
4 bed and 4 bath LUXURY VILLA located in the top rated WINDSOR HILLS RESORT, just 2 MILES / 5 MINUTES AWAY from Walt Disney World This Villa is newly renovated, immaculately clean, and has all you need for a fun and comfortable vacation. The Villa offers the ultimate game room, outdoor dinning, and a screened private pool & spa. All guests also have access to resort amenities. Lots of entertainment for all. * Security Deposit Required with reservation

Gorgeous 3 bed, 2 bath villa w/ pool and jacuzzi
Gorgeous 3 bedroom, 2-bathroom villa set on a 1/4 acre of land, with our own screened, private, heated swimming pool & Jacuzzi, and high speed internet. Situated in a quiet residential community on the sought after Sunridge Woods in Davenport, only 9 miles from Disney. Please note smoking or parties are NOT allowed in house premises. No pool heater available during May through October. **You also MUST be 21 or older to rent this property**
Popular amenities for Windsor Hills villa rentals
Private villa rentals

Casita Kissimmee!Family Vacation Villa! 8minDisney

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

6BR/5BA Disney Villa, Pool+Spa, Water Views, Movie Room

4 Bdrm Villa, 2 miles from Disneyworld at Windsor

South facing Modern villa in quiet gated estate

Beautiful 4 bedrooms with South/West facing pool

The Balmoral Manor: Luxurious & Bright 5BR Oasis

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

Sleeps 20✦Free Pool Heat✦15 min to Disney✦Hot Tub

4mi to Disney | Games | Private Pool

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

Poolside Movies | 3Min.Walk to Waterpark| Game Roo

Luxury Villa/15min2parks/Lakeview/Vgames/Theater

Magical Disney House-Pool & Hot Tub,Free Waterpark

The Golden Bear Villa | Private Pool & Theater

*Private Resort Oasis: Golf-Front, Pool/Spa/Cinema
Villa rentals with a pool

Windsor Hills, Disney/Universal, Pool/SPA, 5BR5BA

4 Miles to Disney - Pretty In Pink

4 Suites Villa near Disney+ Hot Tub@ Magic Village

Luxury 4 Bedrooms, 3.5 Bathrooms with pool.

Disney Fun Time 8BD 4K Movie Theater Jacuzzi Pool

Lakefront Private Pool Villa, 10min to Disney

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

Themed Family Pool Home 10 Min to Disney Game Room
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.ﺇ936 | ﺩ.ﺇ834 | ﺩ.ﺇ735 | ﺩ.ﺇ823 | ﺩ.ﺇ903 | ﺩ.ﺇ1,054 |
| 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.ﺇ404 per night before taxes and fees

Verified guest reviews
Over 3,110 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
80 properties have a dedicated workspace

Wi-Fi availability
150 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
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Universal's Volcano Bay
- Give Kids the World Village
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Aquatica
- Disney's Hollywood Studios
- Camping World Stadium
- ICON Park
- Island H2O Live!
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club




