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Top hotels in Windsor Hills

Minutes Away from Theme Parks! 3-Bed Townhome, 6 minutes to Disney World!

Minutes Away from Theme Parks! 3-Bed Townhome, 6 minutes to Disney World!

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 ...
"My wife and I had a very enjoyable stay. We were very impressed with the level of cleanliness!"

Reviewed on Oct 30, 2026

Opens in a new windowMinutes Away from Theme Parks! 3-Bed Townhome, 6 minutes to Disney World!
Vacation in the Sun! Spacious 3 Bedroom, 6 minutes from Disney World!

Vacation in the Sun! Spacious 3 Bedroom, 6 minutes from Disney World!

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 barbecue grills are available ...
"The trip and home itself was perfect. Only problem we had was starting at about 11pm every night we were there it was constant loud banging and thumping like someone waiting til late at night to do work inside of their home and we really had a hard time sleeping. I came up with that conclusion because ..."

Reviewed on Nov 3, 2026

Opens in a new windowVacation in the Sun! Spacious 3 Bedroom, 6 minutes from Disney World!
TOP-RATED Windsor Hills Resort Villa ♥ THEATER/GAME ROOM, Pool ♥ 4 Mi to Disney

TOP-RATED Windsor Hills Resort Villa ♥ THEATER/GAME ROOM, Pool ♥ 4 Mi to Disney

Kissimmee FL
This vacation home features a gym and a hot tub. Families will appreciate the playground and barbecue grills. A garden and laundry facilities are also ...
"We had plenty of space and bathrooms for everyone to be ready about the same time! Super nice. The resort pool, food, and views were excellent. We stayed a whole day just enjoying the resort on our trip."

Reviewed on Oct 27, 2026

Opens in a new windowTOP-RATED Windsor Hills Resort Villa ♥ THEATER/GAME ROOM, Pool ♥ 4 Mi to Disney
Kissimmee Resort Villa, 4 Bed / 4 Bath En-Suite, Heated South Pool & AC Arcade

Kissimmee Resort Villa, 4 Bed / 4 Bath En-Suite, Heated South Pool & AC Arcade

Kissimmee FL
This villa features an outdoor pool and a gym. Families will appreciate the arcade/game room and barbecue grills. A hot tub and laundry facilities are also ...
"Not our first time staying in the community, but first time at this house. Loved it! Cozy, great layout, spacious. All of the amenities that you could ever need. One slight drawback was that my husband and I found the master suite bed to be uncomfortable, we ended up doing a next day Amazon purchase ..."

Reviewed on Nov 7, 2026

Opens in a new windowKissimmee Resort Villa, 4 Bed / 4 Bath En-Suite, Heated South Pool & AC Arcade
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
This vacation home features an outdoor pool and a hot tub. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available ...
"Very nice property in a gated community. Instructions for check-in were accurate and easy to follow. Host was responsive to messages and property manager was easy to get ahold of with any concerns. Good location to all the premiere attractions and dining options."

Reviewed on Oct 24, 2026

Opens in a new windowFun for kids and parents 6BR/4BA with private pool & hot tub in resort community
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.
"Everything was wonderful. It was very clean.The host had everything ready for us. It does need some furniture upgrades but overall I would stay here again. Thank you for making our trip a wonderful memory."

Reviewed on Oct 11, 2026

Opens in a new windowDream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 8
Newly Totally Renovated-Video Game Room-Private Pool

Newly Totally Renovated-Video Game Room-Private Pool

Kissimmee FL
This vacation home features an outdoor pool and a gym. A hot tub and laundry facilities are also provided.
Opens in a new windowNewly Totally Renovated-Video Game Room-Private Pool
Hidden Gem Resort Community Close to DISNEY!; 3BR/2BA w/ Water Park.

Hidden Gem Resort Community Close to DISNEY!; 3BR/2BA w/ Water Park.

Kissimmee FL
This condo 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 laundry ...
Opens in a new windowHidden Gem Resort Community Close to DISNEY!; 3BR/2BA w/ Water Park.
Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear

Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear

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 barbecue grills are available ...
Opens in a new windowTop-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear
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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.

Recent Windsor Hills hotel reviews by fellow wanderers

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