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Windsor Hills, Kissimmee, Florida, United States of America

Windsor Hills vacation rentals

We found 2,482 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 $91 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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Vacation homes for all, with space for all

Houses

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Condos/Apartments

View 473 Condos/Apartments

Villas

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Studios

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Townhouses

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Resorts

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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
$248 avg/night
(31)

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

Sleeps 8 · 4 Bedrooms · 4 Bathrooms
$299 avg/night
(18)

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

Sleeps 12 · 6 Bedrooms · 4 Bathrooms
$259 avg/night
(1)

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

Sleeps 12 · 6 Bedrooms · 4 Bathrooms
$255 avg/night
(48)

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

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
$115 avg/night
(13)

Disney, 5* - Just 2 stoplights from Disney! Home for those who seek the best!

Sleeps 12 · 6 Bedrooms · 4 Bathrooms
$220 avg/night
(57)

Search 2,482 vacation rentals

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

Great property!

This condo was a perfect place to stay. You are close enough to the Disney area to visit the parks in the day time and come back to enjoy the pool area at night. The rooms were stocked with all the essentials and pretty clean. We would definitely sta...

Julia Z.
Julia Z.
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

Best Vacation EVER

We loved our stay in this lovely peaceful home,The house is extremely well maintained, spotlessly clean and beautifully decorated. The kids loved their themed rooms! All beds were very comfortable too! . Just outside the kitchen is the amazing pool. ...

JACQUELINE U.
JACQUELINE U.
Stayed Apr 2021

Very welcoming

This house was everything that we wanted and more. Plenty of room for 5 adults and 4 kids. It was nice to have a fully stocked and functional kitchen. Not having to pack beach towels was also mind easing. The pictures are exactly what is posted on th...

Kellie S.
Kellie S.
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.
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How many vacation rentals are available around Windsor Hills?

Our 2021 property listings offer a large selection of 2,482 vacation rentals around Windsor Hills. From 1,856 house rentals to 473 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.