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Windsor Hills, Kissimmee, Florida, United States of America

Windsor Hills vacation rentals

We found 2,466 vacation rentals — enter your dates for availability

Discover a selection of 2,500 vacation rentals in Windsor Hills 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 the perfect vacation rental - Windsor Hills

*ALL BRAND NEW* SOUTH POOL & Spa w/FREE HEAT-6Bed/4B RESORT-home/2.5Miles-DISNEY

Sleeps 12 · 6 Bedrooms · 4 Bathrooms
$252 avg/night
(30)

Magical 4 Bedroom Villa with Private Pool Minutes from Disney! Free Pool Heat!

Sleeps 8 · 4 Bedrooms · 4 Bathrooms
$299 avg/night
(19)

2 Massive Water Slides / Giant Kid's Splash Pad / Movie Theater / Fitness Center / Near Disney

Sleeps 12 · 6 Bedrooms · 4 Bathrooms
$238 avg/night
(1)

*"BE OUR GUESTS"/Private luxury pool &spa FREE HEAT/NEW/2.5 MILES to DISNEY

Sleeps 12 · 6 Bedrooms · 4 Bathrooms
$250 avg/night
(49)

3 bed / 2 bath ground floor condo 1 minute away from RESORT POOL AND CLUBHOUS

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
$115 avg/night
(11)

Fully Remodeled~Windsor Hills~2.5 Miles from Disney World Main Entrance

Sleeps 6 · 2 Bedrooms · 2 Bathrooms
$107 avg/night
(46)

Search 2,466 vacation rentals

Reviews are in, families love these Windsor Hills properties
Stayed Apr 2021

Beautiful home- perfect location to Disney

We had such a great time! Play will definitely becoming back to this house! Pool was perfect the spa worked- It was spacious clean everything you would want for a vacation place. It was spacious clean everything you would want for a vacation place. B...

Sheri p.
Sheri p.
Stayed Apr 2021

Better in Person!!

This house is amazing and the pictures don’t do it justice. As a homeowner, I admired the decor and layout of the home but as a vacationing family the house just made sense. We had plenty of room for 12 ppl. You didn’t get in each other’s space and t...

Aneya B.
Aneya B.
Stayed Apr 2021

Great family vacation!

We really enjoyed our stay! The home was very clean and well maintained. All necessities were provided in the home when we arrived. Pool was perfect temp. Communication with property owners and property management team was excellent. Community pool w...

Cory S.
Cory S.
Stayed Apr 2021

Perfect Home for Family Vacation

We just spent over a week in this wonderful home. It is perfect for a family vacation to Disney or other close by attractions. Windsor Hill has lots of amenities and the water park is very nice but our grand children really enjoyed coming home each d...

Kathy H.
Kathy H.
Stayed Apr 2021

Amazing location

Couldn’t recommend this house more. Perfect location, so close to all parks. The house was so clean and perfectly decorated for the kids. Best part was the community pool and splash park Felt like we were at a resort Had a few issues with an alarm b...

Megan G.
Megan G.
Stayed Apr 2021

Disney and Relaxation

The house was beautiful and we were able to host Easter dinner for family that was nearby. Everyone was able to enjoy the heated private pool and relax! Rick was very responsive in any questions I had and also checked in on us while we were there m...

Sami M.
Sami M.
Stayed Mar 2021

Highly Recommend... Would stay here again!

We had a group of 10 family members stay at this property and there was plenty of room for all of us! The little kids LOVED the themed bedrooms. We all loved the game room and swimming pool. The owners of the property always responded almost immediat...

Bobbi C.
Bobbi C.

Granville, Ohio

Stayed Mar 2021

Spring Break March 2021

The house and neighborhood were lovely. It made the trip that much better having all the conveniences of home. After a long day at the parks it was wonderful to come back and take a dip in the pool and relax in the hot tub. Also, this property offers...

Heather D.
Heather D.
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How many vacation rentals are available around Windsor Hills?

Our 2021 property listings offer a large selection of 2,466 vacation rentals around Windsor Hills. From 1,845 house rentals to 469 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.