Windsor Hills, FL

Orlando

An aerial view of a residential area with numerous houses, roads, and several lakes.
A tree with hanging moss and green leaves against a clear blue sky.
A city skyline reflected in a calm lake with modern buildings and trees along the shore.
A palm tree with a brown trunk and red foliage, surrounded by green leaves and red flowers.
Orlando skyline with fireworks, theme park rides, and a castle.

Windsor Hills Hotel Deals

🌴Beautiful home in Windsor Hills Resort -Disney 2.5 miles 🌴

🌴Beautiful home in Windsor Hills Resort -Disney 2.5 miles 🌴

Kissimmee FL
Book a stay at this family-friendly vacation home in Kissimmee. Enjoy free WiFi, private pools, and a fitness center. Popular attractions ESPN Wide World of ...
9.8/10 Exceptional! (200 reviews)
"Great space for family!"

Reviewed on 8 August 2026

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🌴Beautiful home in Windsor Hills Resort -Disney 2.5 miles 🌴
6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ

6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ

Kissimmee FL
Book a stay at this family-friendly vacation home in Kissimmee. Enjoy private pools, a fitness center, and a garden. Our guests praise the helpful staff in our ...
9.4/10 Exceptional! (272 reviews)
"Great location! Neighborhood is cute. Main pool area is amazing. Host was very nice and responded quickly. House has everything you need and was clean."

Reviewed on 30 August 2026

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6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
Newly Totally Renovated-Video Game Room-Private Pool

Newly Totally Renovated-Video Game Room-Private Pool

Kissimmee FL
Stay at this vacation home in Kissimmee. Enjoy private pools, a fitness center, and laundry facilities. Popular attractions ESPN Wide World of Sports Complex ...
9.6/10 Exceptional! (105 reviews)
"Enjoyed our stay! Kids enjoyed the pool. Home was close to Disney. Owners very responsive to any questions we had. Home was clean and comfortable for our family of 5."

Reviewed on 9 August 2026

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Newly Totally Renovated-Video Game Room-Private Pool
Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community

Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community

Kissimmee FL
Book a stay at this family-friendly vacation home in Kissimmee. Enjoy free WiFi, private pools, and a garden. Popular attractions Disney's Animal Kingdom® Theme ...
9.6/10 Exceptional! (88 reviews)
"Great Home, Great location, Great Amenities, close to shops. Host respond take awhile. We didn’t get the pool cleaned. Overall great vacation"

Reviewed on 16 August 2026

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Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community
Villa 2655 - Updated Home w/ Arcade Rm! 3 mi from Disney, Pool Heat, BBQ & PS5

Villa 2655 - Updated Home w/ Arcade Rm! 3 mi from Disney, Pool Heat, BBQ & PS5

Kissimmee FL
Book a stay at this family-friendly vacation home in Kissimmee. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Disney's Animal Kingdom® ...
9.8/10 Exceptional! (83 reviews)
"Truly enjoyed our stay. Great spacious house and very clean. The only suggestion would be a bigger Keurig machine. You’re very close to all the restaurants and you have a Publix, Walmart, and Target nearby. Highly recommend staying here. If you have a disability would not recommend this house. Toilets ..."

Reviewed on 24 July 2026

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Villa 2655 - Updated Home w/ Arcade Rm! 3 mi from Disney, Pool Heat, BBQ & PS5
Tequilla Sunrise at Windsor Hills

Tequilla Sunrise at Windsor Hills

Kissimmee FL
Book a stay at this family-friendly vacation home in Kissimmee. Enjoy free WiFi, private pools, and a fitness center. Popular attractions ESPN Wide World of ...
9.6/10 Exceptional! (76 reviews)
"Clean house, prompt and friendly host."

Reviewed on 26 July 2026

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Tequilla Sunrise at Windsor Hills
See all 1,769 properties in Windsor Hills
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Where to stay in Windsor Hills

Find the best Windsor Hills areas and neighborhoods for the activities you enjoy most.
The entrance to the Hollywood Studios area with a large sign and distinctive architecture.
Photo by Gary Burke
Open Photo by Gary Burke

Bay Lake

A noteworthy feature of Bay Lake is its exciting theme parks. While you're in town, be sure to stop and check out Epcot® and Walt Disney World® Resort.

The entrance to Aquatica with colorful signage and a water slide.

International Drive District

Visitors to International Drive District rave about its breathtaking beach views, exciting theme parks, and popular shops. You might also want to make some time to see Orange County Convention Center or The Orlando Eye while you're exploring the neighborhood.

A golf course with bunkers, water hazards, and a large lake.

Reunion

The waterparks and pristine golf courses are top of the list for many visitors to Reunion. A stop by Reunion Resort Golf Course or Jack Nicklaus Course might round out your trip.

A roller coaster at Universal Orlando Resort, featuring a tall palm tree and a clear blue sky.
Photo by Peter Sutton
Open Photo by Peter Sutton

Florida Center

While visiting Florida Center, you might make a stop by sights like Universal Orlando Resort and Universal Studios Florida.

A large Ferris wheel with blue lighting, surrounded by a parking lot and buildings.

Champions Gate

Abundant dining options and pristine golf courses are well-reviewed features of Champions Gate. Make a stop by top sights like ChampionsGate Golf Club while you're exploring the area.

Windsor Hills, FL

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