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

Windsor Hills Resort vacation rentals

We found 1,077 vacation rentals — enter your dates for availability

Discover a selection of 1,000 vacation rentals in Windsor Hills Resort, 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 private pools and swimming pools. Prices start at $75 per night, and houses and villas are popular options for a stay in Windsor Hills Resort. Either way, you'll find a rental for everyone's needs.
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Find spaces that suit your style

Houses

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Villas

View 199 Villas

Condos/Apartments

View 258 Condos/Apartments

Townhouses

View 216 Townhouses

Studios

View 42 Studios

Find the best place to stay — Windsor Hills Resort

Top floor on Disney's doorstep - Great location

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
$108 avg/night
(110)

Resort Style Living 2 miles from Disney World

Sleeps 8 · 3 Bedrooms · 3 Bathrooms
$113 avg/night
(56)

1.5 miles from Disney! Enjoy HUGE Water Slides, Game Room, and Movie Theater.

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
$119 avg/night
(11)

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

Sleeps 8 · 3 Bedrooms · 3 Bathrooms
$115 avg/night
(143)

2 Bd - 2 Ba Condo 1 1/2 Miles From Disney World Entrance

Sleeps 6 · 2 Bedrooms · 2 Bathrooms
$75 avg/night
(80)

Family owned!!! CLEAN! 130+ stunning reviews! Updated kitchen and bathrooms!

Sleeps 8 · 3 Bedrooms · 2 Bathrooms
$129 avg/night
(172)

Search 1,077 vacation rentals

Top rated rentals — Windsor Hills Resort
Stayed Jun 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 Jun 2022

Disney Vacation

Perfect rental for our week at Disney. Close to the parks, restaurants, and Walmart for essentials. Was exactly as pictured and the pool is a nice perk after a long day. Really enjoyed having a bathroom for each bedroom as well. Great rental, great t...

Sonya S.
Sonya S.
Stayed Jun 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 Jun 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 Jun 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

Gorgeous Condo close to Disney

My family had a wonderful time visiting the Orlando area. This condo was beautiful inside and out. Super clean and had everything we needed. Close to the Disney parks and restaurants. The pool area was truly incredible. My kids really enjoyed this va...

Kristina P.
Kristina P.
Stayed May 2022

Awesome place to stay

What an enjoyable experience for my family of 6 that stayed there over for my granddaughter's 7th birthday. super close to Walt Disney and Sea World had the best time of our lives. the pool in the townhouse was awesome to have as the kids could go wh...

Dawn R.
Dawn R.
Stayed May 2022

Fantastic community

This was a beautiful very well kept neighborhood. The house we chose was perfect for our stay. It was very clean and the perfect amount of space for the 8 of us to be comfortable. The owner was very nice and always easy to get ahold of if needed. We ...

Laura H.
Laura H.

Pensacola

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

Our 2022 property listings offer a large selection of 1,077 vacation rentals around Windsor Hills Resort. From 819 house rentals to 199 villa 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 near Windsor Hills Resort?

Yes, of course. Vrbo has 819 Houses near Windsor Hills Resort. Our other popular types of vacation rentals near Windsor Hills Resort include:

  • Villas: 199 rentals available
  • Condos/Apartments: 258 rentals available
  • Townhouses: 216 rentals available

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

Can I find a vacation rental with pool near Windsor Hills Resort?

Yes, you can select your preferred vacation rental with pool among our 1,051 vacation rentals with pool available near Windsor Hills Resort. Please use our search bar to access the selection of vacation rentals available.

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