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Top hotels in Windsor Hills

Villa 7748 - Updated Home w/ Arcade Rm! 3 mi from Disney, Pool Heat, BBQ & PS5

Villa 7748 - Updated Home w/ Arcade Rm! 3 mi from Disney, Pool Heat, BBQ & PS5

Kissimmee
A water park and an outdoor pool are featured at this smoke-free vacation home. There's fun for all ages with a playground and an arcade/game room, and families ...
10 out of 10 experience! Definitely recommend this stay to everyone looking to visit Orlando. We stayed seven relaxing days. The house was fully equipped with anything and everything you would ever need for a vacation. House is close to parks and resort is super nice and well taken care of. Wendy, ...

Reviewed on Oct 18, 2025

Opens in a new windowVilla 7748 - Updated Home w/ Arcade Rm! 3 mi from Disney, Pool Heat, BBQ & PS5
Our DisneyDreamVilla - minutes to DisneyWorld!!!

Our DisneyDreamVilla - minutes to DisneyWorld!!!

Kissimmee
A water park and an outdoor pool are featured at this smoke-free villa. There's fun for all ages with a playground and an arcade/game room, and barbecue grills ...
Everything was as listed. Beautiful home with plenty of space for a family of 5 and room to spare. The home was spotless and well taken care of. We didn’t end up using the resort amenities but the water slides and splash area looked like fun for the kiddos. The pool area was perfect for relaxing ...

Reviewed on Nov 6, 2025

Opens in a new windowOur DisneyDreamVilla - minutes to DisneyWorld!!!
2 Bedroom, 2 Bath Condo 2 miles from Disney and 10 miles from Universal studios.

2 Bedroom, 2 Bath Condo 2 miles from Disney and 10 miles from Universal studios.

Kissimmee
A water park and an outdoor pool are featured at this smoke-free condo. There's fun for all ages with a playground and an arcade/game room, and families will ...
Although the it was clearly a little older it was well maintained and clean. Kitchen well stocked with utensils/cooking tools. Could use a cheese grater. Appliances all worked great and the unit temperature was easy to maintain. The furniture and beds were comfortable and clean.Be prepared to purchase ...

Reviewed on Oct 2, 2025

Opens in a new window2 Bedroom, 2 Bath Condo 2 miles from Disney and 10 miles from Universal studios.
Great 3 bed condo very close to pool and water park in Windsor Hills Resort

Great 3 bed condo very close to pool and water park in Windsor Hills Resort

Four Corners
A water park and a hot tub are featured at this smoke-free condo. A gym and laundry facilities are also provided.
Great resort feel with the comforts of home! We'll be back

Reviewed on Aug 9, 2025

Opens in a new windowGreat 3 bed condo very close to pool and water park in Windsor Hills Resort
🌴Beautiful home in Windsor Hills Resort -Disney 2.5 miles 🌴

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

Kissimmee
This vacation home features an outdoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite ...
Very nicely kept rental home. Beautiful neighborhood. Would definitely stay at this property again.

Reviewed on Oct 5, 2025

Opens in a new window🌴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
A water park and a hot tub are featured at this smoke-free vacation home. There's fun for all ages with a playground and an arcade/game room, and families will ...
Loved the stay. It's in a nice gated communnity with easy access. Cleanliness and home datedness were acceptable for the price point. Lots of restaurants and stores nearby. The home's swimming pool had a 30 daily surcharge if we wanted it heated. We declined the fee so it was kind of cold. The waterpark ...

Reviewed on Oct 29, 2025

Opens in a new window6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
4 Masters, wifi, private pool, Ultimate gameroom, resort community, 3mi to WDW

4 Masters, wifi, private pool, Ultimate gameroom, resort community, 3mi to WDW

Kissimmee
A hot tub is featured at this vacation home, along with laundry facilities.
The pictures don't do the house justice! It's even nicer in person. The house was clean and just the right size for our party of 7 people! Very convenient to all of the Disney attractions! Would definitely stay here again!

Reviewed on Oct 19, 2025

Opens in a new window4 Masters, wifi, private pool, Ultimate gameroom, resort community, 3mi to WDW
 Windsor Hills Private Luxury Pool House, Sleeps 13

Windsor Hills Private Luxury Pool House, Sleeps 13

Kissimmee
This villa features an outdoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry ...
Disney Vacation
House was just what we needed for our trip to Disney World; the strollers were wonderful to have and the pool was lovely for the kids.

Reviewed on May 23, 2025

Opens in a new window Windsor Hills Private Luxury Pool House, Sleeps 13
Magical Harry Potter Themed Condo

Magical Harry Potter Themed Condo

3 out of 5
Almaton Loop 2813, Kissimmee, FL
An outdoor pool is featured at this apartment, along with free self parking. WiFi in public areas is free. A garden is also provided.
Overall a great stay. Other people are loud at night in upstairs condos but that’s to be expected. The pool area was great. The store on property was very helpful and well priced. They also have good pizza. My only complaint would be no storage in kids room. We had 4 kids with no place to put ...

Reviewed on Apr 11, 2025

Opens in a new windowMagical Harry Potter Themed Condo
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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.

Windsor Hills Hotel Guide

Don’t keep your travel plans on repeat year after year. The same city with the same hotel every season will bore you and give you an itch to go looking for something new. Expand your geographical horizons to more than just those five blocks around your usual haunt.

Nowhere else can you find better deals on Windsor Hills area hotels. You’ll find the best prices on the quirky, the haunted, the old, the new, and the legendary. If you’re wondering what side of the pricing scale some of these hotels fall on, you need not to worry. Compare cheap hotels near Windsor Hills to find the perfect one to will fit your budget.

Leave the ordinary routine you’re set on behind and go. Go anywhere you want. Anywhere that makes you think, “I wonder what that’s like?” Part of Travelocity’s mission is to get you off-the-beaten path and the hotels near Windsor Hills are perfect for that. Find your new favorite watering hole on a quiet street. Discover a place to escape for the weekend with tasty local fare and unique sights. We want you to consider the places outside your normal comfort zone. Browse our selection and find the ideal hotel, in a place you’d like to explore.

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