Windsor Hills Resort - Kissimmee, FL Vacation Rentals

Compare 11 vacation rentals with savings up to 30% off this summer.
USA > Florida > Windsor Hills Resort - Kissimmee, FL

Make Windsor Hills Resort - Kissimmee, FL your next getaway

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
Almaton Luxury 205 - Windsor Hills
3 Bedroom | 2 Bath | Sleeps 6 (4 Adults Max)

Almaton Luxury 205 - Windsor Hills - Kissimmee, FL

$101 avg / night
Chilla Villa - Windsor Hills
3 Bedroom | 3 Bath | Sleeps 6

Chilla Villa - Windsor Hills - Kissimmee, FL

$120 avg / night
Almaton Loop Livin'
3 Bedroom | 2 Bath | Sleeps 7

Almaton Loop Livin' - Kissimmee, FL

$123 avg / night
Almaton Magic
3 Bedroom | 2 Bath | Sleeps 8

Almaton Magic - Kissimmee, FL

$117 avg / night
Family Fiesta - Windsor Hills
3 Bedroom | 2 Bath | Sleeps 8

Family Fiesta - Windsor Hills - Kissimmee, FL

$106 avg / night

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Recent Windsor Hills Resort - Kissimmee, FL vacation rental reviews

Very nice and spacious. The beds are comfortable! Everything I needed was right there in the condo. I will definitely stay there again!
jason g. | Jun 2023
We enjoyed our family vacation to the Orlando parks and outlet shopping. The condo could use some décor updating (my opinion) but we were grateful that it was clean and plenty spacious for our family of 5. The property management team was attentive when we requested extra pillow cases.
Molly M. | May 2023
Todo hermoso, seguro, variedad de actividades. Silencioso acogedor es sentirte en casa me encanto la experiencia lo recomiendo
KELLIE P. | May 2023
Windsor Hills Resort - Kissimmee, FL vacation rental FAQ

Yes. 11 of our Windsor Hills Resort - Kissimmee, FL vacation rentals have internet access, so you can stay connected throughout your trip.

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Some of the most popular amenities in our Windsor Hills Resort - Kissimmee, FL vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Windsor Hills Resort - Kissimmee, FL team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Windsor Hills Resort - Kissimmee, FL, log in to Trip Manager to see options available for your specific trip.

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