Windsor Hills Resort - Kissimmee, FL Vacation Rentals

Compare 12 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 12 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

Popular
Dog-friendly Hot tub Internet
Mickey's Magical Escape 3D Tour
3 Bedroom | 3 Bath | Sleeps 6

Mickey's Magical Escape - Kissimmee, FL

From $99
Mickey's Magic at Windsor Hills Resort 3D Tour
3 Bedroom | 3 Bath | Sleeps 8

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

From $119
Almaton Luxury - 205 3D Tour
3 Bedroom | 2 Bath | Sleeps 6 (4 Adults Max)

Almaton Luxury - 205 - Kissimmee, FL

From $95
Mickey’s Hideaway 3D Tour
2 Bedroom | 2 Bath | Sleeps 6

Mickey’s Hideaway - Kissimmee, FL

From $65
Almaton Magic 3D Tour
3 Bedroom | 2 Bath | Sleeps 8

Almaton Magic - Kissimmee, FL

From $114

View 7 more homes

Recent Windsor Hills Resort - Kissimmee, FL vacation rental reviews

My family spent the last week of the year in this property and we had a blast! Everything is new and the resort pool was great as well. The only downside was getting access to the apartment - took a little longer than expected but not a big deal. We enjoyed our stay overall.
Luis L. | Jan 2022
Love this place! So spacious, comfortable, and fun for the whole family. Love the beautiful new tile and pool lights! The pics on website need an update bc it looks so much nicer once you arrive.
Sheryl G. | Jan 2022
This home looks exactly as pictured and the ambiance is superb. Security presence made me feel extremely safe. My family enjoyed all the resort’s amenities as well as the ones right at the condo. I really appreciated being near shopping centers, gas stations, restaurants, and of course Disney. It was so refreshing to actually relax and enjoy everything this home offered that i didn't want to leave. I will most definitely book this home again in the future. This listing deserves a 5 diamond rating..
Lashenia S. | Dec 2021

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