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Windsor Hills Resort, Kissimmee, Florida, United States of America

Windsor Hills Resort holiday rentals

We found 1,090 holiday rentals — enter your dates for availability

Discover a selection of 1,000 holiday home rentals in Windsor Hills Resort, Kissimmee that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Stayz holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at AU$ 183 per night, and holiday houses and flats & apartments are popular options for a stay in Windsor Hills Resort. Either way, you'll find holiday accommodation for everyone's needs.
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Find spaces that suit your style

Houses

View 821 Houses

Condos/Apartments

View 269 Condos/Apartments

Villas

View 202 Villas

Townhouses

View 216 Townhouses

Studios

View 55 Studios

Find the best place to stay — Windsor Hills Resort

Chip & Dale's Treehouse

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
AU$ 228 avg/night
(110)

WindsorHills Orlando TownHome

Sleeps 8 · 3 Bedrooms · 3 Bathrooms
AU$ 215 avg/night
(57)

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
AU$ 220 avg/night
(11)

Whipple's Townhouse

Sleeps 8 · 3 Bedrooms · 3 Bathrooms
AU$ 209 avg/night
(170)

WINDSOR HILLS

Sleeps 6 · 2 Bedrooms · 2 Bathrooms
AU$ 226 avg/night
(81)

Figment's Imagination

Sleeps 8 · 3 Bedrooms · 2 Bathrooms
AU$ 263 avg/night
(172)

Search 1,090 holiday rentals

Top rated rentals — Windsor Hills Resort
Stayed June 2022

Will never use a hotel again this was awesome

The house was wonderful and beautiful this was my first time renting a home for vacation instead of a hotel and I’m hooked the experience was amazing I loved that all the kids and us parents all had our own rooms and bathrooms and the pool really fil...

Christopher A.
Christopher A.
Stayed June 2022

Second stay

We stayed at this same property last year for a volleyball tournament. We loved it the first year and the few problems (mainly, broken dishwasher) we had this year were addressed immediately by the owner. The space is great and location is perfect ...

Jenny T.
Jenny T.
Stayed June 2022

Great Value for a Quiet Condo with an Amazing Pool

If you are looking for a two bedroom condo perfect for two parents and two children, this is it! The two bathrooms were spacious as well as the walk-in closets. The kitchen had everything you need. The screened-in porch was a great place to apply sun...

Rebecca M.
Rebecca M.
Stayed June 2022

Amazing

This property is amazing !!! It’s clean the beds are amazing best sleep I’ve had in years the pool is amazing , just a 3 minute walk to the club house . Oh he kids named it the Minnie house we stayed 7 days and it was not enough time . Home owner is ...

LORI W.
LORI W.
Stayed June 2022

Perfect Stay!

I am so glad that we decided to stay off the Disney property. This was a wonderful base location for our Disney trip. We originally thought we would be traveling with a dog and a couple of additional family members. In the end, it was just me, my hus...

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Louisiana

Stayed June 2022

Great stay

Great stay at this property. Really fabulous location, great pool and the property was really clean. My only issue was with the lock on the front door, not that great. However we made it work. Also the carpets could do with an upgrade. Thanks agai...

Claire M.
Claire M.
Stayed May 2022

Must stay

This home was clean, and cozy. We felt safe and secure at this location. They provided all the basics necessities during our stay. My kids love it and so did we. The only issue I had was at time for check in, I didnt know how to access the house. I s...

Lori L.
Lori L.
Stayed May 2022

Amazing place I would stay again

Amazing place I would stay again It was a beautiful place it was exactly what I thought and what it said it would be the only thing it would’ve been nice to know was that we had to go to the welcome center to get the wristbands to get into the pool n...

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How many holiday accommodation are available around Windsor Hills Resort?

Our 2022 accommodation listings offer a large selection of 1,090 holiday rentals around Windsor Hills Resort. From 821 holiday houses to 269 flats & apartments, find unique holiday homes for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

Can I rent Houses near Windsor Hills Resort?

Yes, of course. Stayz has 821 Houses near Windsor Hills Resort. Our other popular types of holiday homes near Windsor Hills Resort include:

  • Condos/Apartments: 269 holiday houses
  • Villas: 202 holiday houses
  • Townhouses: 216 holiday houses

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

Can I find a holiday accommodation with pool near Windsor Hills Resort?

Yes, you can select your prefered holiday accommodation with pool among our 1,055 holiday rentals with pool available near Windsor Hills Resort. Please use our search bar to access the selection of rentals available.

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