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

Windsor Hills Resort vacation rentals

We found 1,032 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 pool and pool. Prices start at C$ 110 per night, and house rentals and villa rentals 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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Houses

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Villas

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Condos/Apartments

View 254 Condos/Apartments

Townhouses

View 167 Townhouses

Studios

View 38 Studios

Find the best place to stay — Windsor Hills Resort

Chip & Dale's Treehouse

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
C$ 149 avg/night
(113)

Whipple's Townhouse

Sleeps 8 · 3 Bedrooms · 3 Bathrooms
C$ 207 avg/night
(176)

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
C$ 154 avg/night
(16)

Figment's Imagination

Sleeps 8 · 3 Bedrooms · 2 Bathrooms
C$ 167 avg/night
(175)

Retreat Villa

Sleeps 8 · 3 Bedrooms · 2 Bathrooms
C$ 226 avg/night
(101)

WINDSOR HILLS

Sleeps 6 · 2 Bedrooms · 2 Bathrooms
C$ 115 avg/night
(83)

Search 1,032 vacation rentals

Top rated rentals — Windsor Hills Resort
Stayed Jul 2022

Great condo!

The condo was very nice spacious and comfortable for 6 of us. Everything was decorated beautifully. The pool area was crowded but we didn’t really use the pool since we had other activities planned. It was close to many attractions, stores and rest...

Peggy N.
Peggy N.
Stayed Jul 2022

Florida condo

This was perfect for our family. We spent 5 days in Dianey and 3 in universal. The condo was close to both parks and plenty of grocery shopping and food options. It was nice having the option to hang in the backyard with a private pool or hit the pub...

Jennifer C.
Jennifer C.
Stayed Jul 2022

Our Best Week Ever!

This beautiful home was just as advertised....very clean, plenty of kitchen utensils, pool towels and game room toys. Nice, working flat screen TVs in every room, ALL THE REMOTES HAD BATTERIES AND WORKED! We have deaf family members and had an issue ...

Kathleen G.
Kathleen G.
Stayed Jul 2022

Will stay again!

This property had everything we needed. Our kids loved the pool on the patio. All the rooms had night lights, kitchen had pot holders and a pizza cutter! (I know this is super simple but it makes a big difference) rooms were clean, comfortable beds/b...

Kendra H.
Kendra H.
Stayed Jul 2022

Great place at a great price

It was a wonderful stay located near anything you may need or want to do. Our trip was just to have a relaxing pool side wkend and that it was. The arcade / pool table was a lot of fun as well. The master bed was very comfy and plenty of towels for t...

Molly C.
Molly C.
Stayed Jul 2022

Yet another great stay at Windsor Hills!

Any time we are in Orlando, we always check for properties in Windsor Hills. This was the first time we have stayed in this particular townhouse, and it did not disappoint! There was ample space in the 3 bedrooms for 4 adults and 1 teen (and could co...

Richard C.
Richard C.
Stayed Jul 2022

Satterwhite Family July 2022

I must say I was skeptical reading the other reviews. I even told my husband I think I made a mistake. But I must say when we arrived we were truly amazed! The condo was beautiful and clean. Our king bed slept so comfortable all week. Our girls loved...

Tarsha S.
Tarsha S.
Stayed Jul 2022

Great place—great communication—would recommend!

Great location and close to the Disney parks. We loved the pool area! Wonderful and quick communication with property manager & owner. The only complaint (& I use that word loosely bc it didn’t put a damper on our stay) but the beds in this unit coul...

Amy M.
Amy M.
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How many vacation rentals are available around Windsor Hills Resort?

Our 2022 vacation rental listings offer a large selection of 1,032 house rentals around Windsor Hills Resort. From 778 house rentals to 224 villa rentals, find unique vacation rental for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Windsor Hills Resort is on Vrbo.

Can I rent Houses near Windsor Hills Resort?

Yes, of course. Vrbo Canada has 778 Houses near Windsor Hills Resort. Our other popular types of vacation rentals near Windsor Hills Resort include:

  • Villas: 224 lodging choices
  • Condos/Apartments: 254 lodging choices
  • Townhouses: 167 lodging choices

But you can also enjoy a great stay in one of our other vacation homes 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 1,003 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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