Windsor Hills, FL
Orlando
Visit Windsor Hills
Things to do
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
￥4,846
per adult
92% of travellers recommend
Universal Orlando Resort Express Passes
￥20,048
per traveler
80% of travellers recommend
Universal Orlando Resort Theme Park Tickets
￥20,883
per adult
78% of travellers recommend
Walt Disney World® Resort Theme Park Tickets
￥20,929
per adult
Windsor Hills Hotel Deals
Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear
Kissimmee FL
Book a stay at this family-friendly vacation home in Kissimmee. Enjoy free WiFi, private pools, and a fitness center. Our guests praise the pool and the helpful ...
10/10 Exceptional! (388 reviews)
"Quick to respond, beautiful property, amazing family vacation, would definitely return"
Reviewed on Sep 24, 2026
Minutes Away from Theme Parks! 3-Bed Townhome, 6 minutes to Disney World!
Kissimmee FL
Book a stay at this family-friendly vacation home in Kissimmee. Enjoy free WiFi, private pools, and a fitness center. Our guests praise the helpful staff in ...
10/10 Exceptional! (217 reviews)
"This townhouse was the perfect place to stay! Kids loved the pools and access to arcade games, adults loved the comfortable beds. Kitchen was stocked with everything needed. Location was close to restaurants and shopping. We will be back!"
Reviewed on Oct 8, 2026
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! (108 reviews)
"The property was beautiful, nice and roomy, communication was great, the pool in the back yard kept the kids entertained. There were a couple things brought up to the owners about the kids room, they quickly sent over the property management team. Overall we couldn't ask for a better stay!"
Reviewed on Oct 11, 2026
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! (90 reviews)
"The place was great. Close to both Disney and Universal. A few things were broken when we got there, but we were so busy it was no big deal. Also they left half a roll of toilet paper in each bathroom and that was it and 2 trash bags for the whole week when you have to double bag the trash. But other ..."
Reviewed on Sep 26, 2026
EPIC! Themed-Arcade-Theatre-Pool Table-Pool&Spa-3mi>Disney
Kissimmee FL
Book a stay at this family-friendly vacation home in Kissimmee. Enjoy free WiFi, private pools, and a water park. Popular attractions Disney's Animal Kingdom® ...
10/10 Exceptional! (12 reviews)
Absolutely magical stay at The Southern Isles!
"We just got back from 18 nights at The Southern Isles in Windsor Hills and it completely exceeded our expectations. From the moment we walked in, we knew we'd made a great choice. This place is loaded — six bedrooms, and the theming alone makes it worth booking: our kids were thrilled with the Frozen ..."
Reviewed on Aug 29, 2026
Windsor Hills Town Home! So Close You Can Feel the Magic!
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 ...
6.8/10 (35 reviews)
"The townhouse was pretty clean. It was a great budget get away for a weekend. Would stay again."
Reviewed on Sep 7, 2026
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.
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.
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 neighborhood.
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.
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.
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.
