Windsor Hills

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.

Things to do


Top hotels in Windsor Hills

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
Stay at this family-friendly villa in Kissimmee. Enjoy free Wi-Fi, private pools and a fitness centre. Our guests praise the pool and the property condition ...
9.8/10 Exceptional! (177 reviews)
"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 7 Nov 2026

Kissimmee Resort Villa, 4 Bed / 4 Bath En-Suite, Heated South Pool & AC Arcade
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
Stay at this family-friendly holiday home in Kissimmee. Enjoy free Wi-Fi, private pools and a fitness centre. Our guests praise the helpful staff in their reviews. ...
10/10 Exceptional! (220 reviews)
"My wife and I had a very enjoyable stay. We were very impressed with the level of cleanliness!"

Reviewed on 30 Oct 2026

Minutes Away from Theme Parks! 3-Bed Townhome, 6 minutes to Disney World!
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
Stay at this family-friendly holiday home in Kissimmee. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Disney's Animal Kingdom® Theme Park ...
9.6/10 Exceptional! (92 reviews)
"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 24 Oct 2026

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

Newly Totally Renovated-Video Game Room-Private Pool

Kissimmee FL
Stay at this holiday home in Kissimmee. Enjoy private pools, a fitness centre and laundry facilities. Popular attractions ESPN Wide World of Sports Complex and ...
Newly 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
Stay at this family-friendly condo in Kissimmee. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions ESPN Wide World of Sports Complex and Disney's ...
Hidden Gem Resort Community Close to DISNEY!; 3BR/2BA w/ Water Park.
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
Stay at this family-friendly holiday home in Kissimmee. Enjoy free Wi-Fi, private pools and a fitness centre. Our guests praise the helpful staff in their reviews. ...
10/10 Exceptional! (130 reviews)
"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 3 Nov 2026

Vacation in the Sun! Spacious 3 Bedroom, 6 minutes from Disney World!
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 for the activities you enjoy most.

Bay Lake

Exciting theme parks plentiful wildlife and top sights from Epcot® to Walt Disney World® Resort – discover Bay Lake, a destination also famous for its entertainment.

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 Orange County Convention Center North while you're exploring the neighbourhood.

Florida Center

If you're spending some time in Florida Center, Universal Orlando Resort and Universal Studios Florida are top sights worth seeing.

Champions Gate

Ample dining options and top 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.

Reunion

The top golf courses and fun-filled water parks 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.



Windsor Hills

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