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Windsor Hills, Four Corners, Florida, United States of America

Windsor Hills vacation rentals

We found 2,347 vacation rentals — enter your dates for availability

Discover a selection of 2,500 vacation rentals in Windsor Hills, Kissimmee that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $85 per night, and houses and condos are popular options for a stay in Windsor Hills. Either way, you'll find a rental for everyone's needs.
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Find spaces that suit your style

Houses

View 1,728 Houses

Condos/Apartments

View 461 Condos/Apartments

Villas

View 561 Villas

Studios

View 87 Studios

Townhouses

View 323 Townhouses

Resorts

View 153 Resorts

Find the best place to stay — Windsor Hills

Newly renovated townhome near theme parks w/complimentary splash pool heat!

Sleeps 7 · 3 Bedrooms · 3 Bathrooms
$151 avg/night

Windsor Hills Resort - Pool View and 2 miles from Disney World!

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
$105 avg/night

Resort Style Living 2 miles from Disney World

Sleeps 8 · 3 Bedrooms · 3 Bathrooms
$85 avg/night
(50)

3 BR * 2 Miles to Disney, pool, spa, water park, game room, free WiFi and more

Sleeps 8 · 3 Bedrooms · 3 Bathrooms
$110 avg/night
(129)

Safety Fenced Pool & Spa Villa House — 10 minutes to DisneyWorld!

Sleeps 11 · 5 Bedrooms · 5 Bathrooms
$189 avg/night
(119)

Remodeled 2021 Gated Windsor Hills Resort - 2 Miles 2 World Drive - No Carpets

Sleeps 4 · 2 Bedrooms · 2 Bathrooms
$103 avg/night
(102)

Search 2,347 vacation rentals

Top rated rentals — Windsor Hills
Stayed Sep 2021

Thank you!

This place is great for little ones. The furniture isnt the best but everything else is amazing! It's super close to Walmart and disney, and everyone is super friendly. The kids loved Frank at the gate! Thank you for having us, we needed this little ...

Amanda P.
Amanda P.
Stayed Sep 2021

Amazing Stay

Everything about the experience was immaculate and smooth. The house was furnished fully as advertised, had some very nice touches such as themed rooms and baths, kids also spend alot of time in the game room playing air hockey and billiard. Lastly...

Thomas N.
Thomas N.
Stayed Aug 2021

Perfect

I traveled to Orlando with my kids. The house was perfect for us. Plenty of space. It was so clean and perfectly decorated. It was the perfect location. The neighborhood was super secure. Everything was perfect. I really enjoyed my stay, hope to come...

Krystal C.
Krystal C.
Stayed Aug 2021

Vacation Stay

Great location, and the property was well suited for our needs. Our 2 year old loved the Mickey room and the split floor plan worked worked well. It was nice to have the small pool in addition to the large clubhouse pool. Overall, we enjoyed the st...

Scott W.
Scott W.
Stayed Aug 2021

Perfect family place

Took our kids on a trip we had planned for years. No plans, just knew we wanted Florida. This was the perfect spot to go any direction we needed. Also a private small pool or large community too. Very clean and definitely perfect for us. Would DEFINI...

Angie B.
Angie B.
Stayed Aug 2021

Fabulous!!

If you are searching for a rental THIS IS THE PLACE! We had such a great time. The game room is great for tweens and teens. If we weren't at the parks, they were in the game room. The house itself was immaculate. We stay in lots of vacation rental ho...

Selina B.
Selina B.
Stayed Jul 2021

Wonderful, would visit again

The Windsor Hills resort had a great salt water pool with the deepest being 4'10" so perfect for us to walk or swim around alongside our kids. There were two waterslides and a water playground for our kids to enjoy. There was a workout facility, arca...

Ireli B.
Ireli B.
Stayed Jul 2021

Amazing

Paul was great. He will respond to all my emails fairly quickly . Answered all my questions. We definitely enjoyed our time in Orlando. The house was just perfect. It was nice to come home and the pool was just the perfect temperature. Close to a lo...

diana d.
diana d.

Laurel

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How many vacation rentals are available around Windsor Hills, Kissimmee?

Our 2021 property listings offer a large selection of 2,347 vacation rentals around Windsor Hills. From 1,728 house rentals to 461 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Windsor Hills?

Yes, of course. Vrbo has 1,728 Houses in Windsor Hills. Our other popular types of vacation rentals in Windsor Hills include:

  • Condos/Apartments: 461 rentals available
  • Villas: 561 rentals available
  • Studios: 87 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Townhouses and more.

Can I find a vacation rental with pool in Windsor Hills?

Yes, you can select your preferred vacation rental with pool among our 2,207 vacation rentals with pool available in Windsor Hills. Please use our search bar to access the selection of vacation rentals available.