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Top hotels in Windsor Hills

Amazing 6-bedroom Villa with Private Pool Minutes from Disney! 5 Star Theming!

Amazing 6-bedroom Villa with Private Pool Minutes from Disney! 5 Star Theming!

Kissimmee FL
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 ...
"Fun Disney themed home with special touches made the magic alive! Clean, spacious, AC was consistent and pool was on spot after some hot days at the park. Nice quiet neighborhood with no rear neighbors, has a view of a valley behind. Very close to Disney and Walmart/Target with lots of other convenience. ..."

Reviewed on Jul 23, 2026

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Opens in a new windowAmazing 6-bedroom Villa with Private Pool Minutes from Disney! 5 Star Theming!
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 FL
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 ...
"The rental was very family friendly. It was clean, beds was comfortable. It was big enough for our family to move around and navigate through the house with out bumping into each other. We loved the house and the hot tub was lovely. Host also is very responsive"

Reviewed on Aug 2, 2026

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Opens in a new windowVilla 7748 - Updated Home w/ Arcade Rm! 3 mi from Disney, Pool Heat, BBQ & PS5
Livin the Dream❤️Closest FREE Resort to Disney! 3 Kings

Livin the Dream❤️Closest FREE Resort to Disney! 3 Kings

Kissimmee FL
$502 nightly
The price is $560 total per night from Sep 7 to Sep 8
$560 total
Sep 7 - Sep 8
Total with taxes and fees
A water park and a hot tub are featured at this smoke-free vacation home. Families will appreciate the arcade/game room and onsite laundry facilities. Enjoy ...
"The place was advertised exactly as seen listed and host is super friendly and responsive. Highly recommend the stay here and the game room was super cool."

Reviewed on Jul 25, 2026

Opens in a new windowLivin the Dream❤️Closest FREE Resort to Disney! 3 Kings
🌴Beautiful home in Windsor Hills Resort -Disney 2.5 miles 🌴

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

Kissimmee FL
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 ...
"Amazing stay for almost 3 weeks July/aug. Windsor hills is a lovely secure area and the pool being so close was perfect for the kids. We didn’t need to use the small pool at the townhouse very much as we spent a couple of hours at the communal pool/water slides/table tennis etc. the house was bigger ..."

Reviewed on Aug 6, 2026

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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 FL
This vacation home features a gym and a hot tub. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite ...
"The house was as described in the listing. We had a party of 13 and everyone had a place to sleep and eat. Check-in and check-out were easy and we were close to everything we needed."

Reviewed on Aug 9, 2026

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Opens in a new window6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
Dream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 8

Dream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 8

Kissimmee FL
This condo features laundry facilities.
"The property, the home, the amenities and the staff were all excellent. Check in was a breeze and the communication with the host was quick, clear and positive. The home was everything it was described to be with some of the cutest decorative touches I’ve ever seen."

Reviewed on Jul 29, 2026

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Opens in a new windowDream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 8
C4 Family Vacation close to Disney Theme Park

C4 Family Vacation close to Disney Theme Park

Kissimmee FL
This apartment features laundry facilities.
"Everything was spotless and so welcoming!!! Definitely gonna stay here again. Easy process & great communication. The kids loved the room. Perfect for kids. Pool was so nice"

Reviewed on Aug 5, 2026

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Opens in a new windowC4 Family Vacation close to Disney Theme Park
Magical Memories in Windsor Hills Resort

Magical Memories in Windsor Hills Resort

Four Corners FL
This villa features an outdoor pool and a hot tub. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite ...
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Opens in a new windowMagical Memories in Windsor Hills Resort
Livin Great❤️3 King Suites, FREE Resort, Private South Pool

Livin Great❤️3 King Suites, FREE Resort, Private South Pool

Kissimmee FL
A water park and a hot tub are featured at this smoke-free vacation home. Families will appreciate the arcade/game room and onsite laundry facilities. A gym ...
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Opens in a new windowLivin Great❤️3 King Suites, FREE Resort, Private South Pool
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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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