Windsor Hills Resort - Kissimmee, FL Vacation Rentals

Compare 11 vacation rentals. Enter your trip dates to get started.
USA > Florida > Windsor Hills Resort - Kissimmee, FL

Make Windsor Hills Resort - Kissimmee, FL your next getaway—choose from 11 great vacation rentals

If you like the finer things in life and yearn for a sun-filled getaway but don't want to break the bank, our vacation rentals at Windsor Hills Resort are for you! From single-bedroom villas to our luxurious five-bedroom executive villas with access to a pool, spa, and a Jacuzzi, not to mention other resort-style amenities, this 24-hour gated community is worth a look when you're passing through family-friendly Kissimmee.

Windsor Hills Resort - Kissimmee, FL vacation rentals for every getaway

Dog-friendly Hot tub Internet
Mickey’s Hideaway 3D Tour
2 Bed | 2 Bath | Sleeps 6

Mickey’s Hideaway - Kissimmee, FL

From $120
Shangri-la at Windsor 3D Tour
3 Bed | 2 Bath | Sleeps 8

Shangri-la at Windsor - Kissimmee, FL

From $161
Mickey's Magic at Windsor Hills Resort 3D Tour
3 Bed | 3 Bath | Sleeps 8

Mickey's Magic at Windsor Hills Resort - Kissimmee, FL

From $142
Mickey's Magical Escape 3D Tour
3 Bed | 3 Bath | Sleeps 6

Mickey's Magical Escape - Kissimmee, FL

From $125
Chilla Villa 3D Tour
3 Bed | 3 Bath | Sleeps 6

Chilla Villa - Kissimmee, FL

From $124

View 6 more homes

Recent Windsor Hills Resort - Kissimmee, FL vacation rental reviews

Beautiful house in an awesome neighborhood just a few miles from Disney. We really enjoyed our stay.
Rachel D. | May 2022
Great location! Easy commute to all the attractions. Loved the private pool and community pool.
Michelle A. | May 2022
Clean and comfortable unit! Nice location with the pond behind the unit and pool just a short walk away but far enough to be away from the noise and people.
Chad H. | May 2022

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Where is Windsor Hills Resort?

Our Windsor Hills Resort vacation rentals are located just two miles from Disney World, so it's the perfect place to rest up after fun-filled days in the amusement park. The resort is also about 24 miles from the International Airport in Orlando, so you'll have an easy time reaching your vacation rental after your flight. An adventure into downtown Orlando is easy, as well - just follow I-4 E all the way there.

Things to Do at Windsor Hills Resort

One of Windsor Hills Resort's most alluring features is the double Olympic-size pool. Take a swim or recline on a lounger while the kids play in the toddler pool, fountains, and spiral water slide. Follow up with a soak in the hot tub while you take in the Florida scenery.

For family fun time, head to the castle-themed playground for a game of giant chess or have a turn on the merry-go-round and swings. There is a picnic and barbecue area for grilling while the clubhouse has billiards and a video arcade for indoor fun. The 48-seat movie theater is a great place to beat the heat and enjoy a free movie.

If you want to maintain your fitness regimen, you'll have ample opportunity. Perfect your swing at the tennis courts or Championship golf course, work on your swish on the basketball court, or master your cut shot on the volleyball court. Head to the fitness center for cardio equipment and weight training.

Villas at Windsor Hills Resort

The villas are a vacation unto themselves with 3,000 square feet of living space, AC, and flatscreen cable TVs in every room. The decor is luscious and upscale, boasting stylish furnishings, plush pillows, and silk accents throughout. The kids' rooms have their own bathrooms and are themed to capture imaginations and create lasting memories. The state-of-the-art kitchen has everything the chefs in your group need to make hearty, delicious meals. Other amenities include WiFi, a safe for your valuables, a Tiki Bar, and an on-site grocery store.

When you come to Florida for tropical breezes and golden sunshine, be sure to check out our Windsor Hills vacation rentals for a truly relaxing stay with convenience and comfort.

Photo Credit: Maurício Padovani via Flickr