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Windsor Hills, Kissimmee, Florida, United States of America

Windsor Hills holiday rentals

We found 2,455 holiday rentals — enter your dates for availability

Discover a selection of 2,500 holiday home rentals in Windsor Hills 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$ 173 per night, and holiday houses and flats & apartments are popular options for a stay in Windsor Hills. Either way, you'll find holiday accommodation for everyone's needs.
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Find the best place to stay — Windsor Hills

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

Sleeps 12 · 6 Bedrooms · 4 Bathrooms
AU$ 487 avg/night
(31)

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

Sleeps 8 · 4 Bedrooms · 4 Bathrooms
AU$ 531 avg/night
(19)

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

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
AU$ 209 avg/night
(11)

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

Sleeps 6 · 2 Bedrooms · 2 Bathrooms
AU$ 218 avg/night
(48)

🌴WindsorHills*Disney 2.5 miles*3b/3b*5-star Resort *end unit*updated🌴

Sleeps 8 · 3 Bedrooms · 3 Bathrooms
AU$ 274 avg/night
(79)

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

Sleeps 12 · 6 Bedrooms · 4 Bathrooms
AU$ 572 avg/night
(48)

Search 2,455 holiday rentals

Top rated rentals — Windsor Hills
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

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

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 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.
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How many holiday accommodation are available around Windsor Hills?

Our 2021 accommodation listings offer a large selection of 2,455 holiday rentals around Windsor Hills. From 1,844 holiday houses to 465 flats & apartments, find unique holiday homes for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Windsor Hills is on Stayz.