List your Property
Windsor Hills Resort, Kissimmee, Florida, United States of America

Windsor Hills Resort holiday lettings

We found 1,146 holiday rentals — enter your dates for availability

Discover a selection of 1,000 holiday rentals in Windsor Hills Resort, Kissimmee that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including private pool and pool. Prices start at £ 118 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.
DynamicDestinationRefinements
AsyncDestinationUrgency
Find spaces that suit your style

Houses

View 849 Houses

Villas

View 235 Villas

Townhouses

View 186 Townhouses

Flats

View 297 Flats

Studios

View 69 Studios

Find the best place to stay — Windsor Hills Resort

Chip & Dale's Treehouse

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
£ 148 avg/night
(128)

Almaton Luxury 205 - Windsor Hills

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
£ 161 avg/night
(121)

Mickeys Dream Home

Sleeps 6 · 2 Bedrooms · 2 Bathrooms
£ 152 avg/night
(97)

Mickey's Hangout

Sleeps 6 · 2 Bedrooms · 2 Bathrooms
£ 159 avg/night
(113)

Sleeps 6 · 3 Bedrooms · 3 Bathrooms
£ 163 avg/night
(39)

2821Almon

3 Bedrooms · 2 Bathrooms
£ 199 avg/night

Search 1,146 holiday rentals

Top rated rentals — Windsor Hills Resort
Stayed Mar 2023

One day stay

The location was very nice, the townhouse was beautiful and felt very welcoming! The kids enjoyed the pool with the toys and inflatables provided. The owner was very easy to comunicate with and was responsive. The kids were able to use the clubhouse ...

Raquel S.
Raquel S.
Stayed Feb 2023

Great pool and location, very good basic unit for families

This was a great stay, the pool exceeded expectations and we were close to theme parks and necessities. The unit was exactly what we expected based on the photos. Clean and basic, there was significant wear on some furniture/surfaces but that's to be...

Christine B.
Christine B.
Stayed Feb 2023

Great Stay

This property worked amazing for our family of 5. Great location, awesome little water park. We didn't spend a lot of time here, but it was a great space to land after a busy day at the theme parks nearby. We enjoyed access to disney + and the other ...

Stacy J.
Stacy J.
Stayed Feb 2023

Home Away from Home

Our stay was amazing in every way. Sunil was very quick to respond to all of my questions via email before our arrival. Check in was the easiest I've ever experienced. The condo was very clean and comfortable. The king sized bed in the master bedroom...

Angela M.
Angela M.
Stayed Feb 2023

Great location!

We loved our stay! We went to Disney parks most of the time & it was great being able to swim after a long park day. It’s only a few miles from the parks & convenient to stores & restaurants. The townhouse was clean, the private heated pool was great...

Mary M.
Mary M.

Powder Springs, GA

Stayed Feb 2023

Great Family Friendly Vacation Home!!

This property was clean, conveniently located and truly felt like home! The host was extremely responsive from booking through to checkout. Checkin went smoothly and the property itself is beautiful. The unit we were in was modern and tastfully decor...

Amber C.
Amber C.
Stayed Feb 2023

3 bedroom townhouse

We truly enjoyed our stay at Windsor Hills. Our host was fantastic! She communicated promptly and was wonderful about relaying information we would need. The home was comfortable but could use some updates. We loved and enjoyed the pool. It’s small b...

Cynthia H.
Cynthia H.
Stayed Jan 2023

Nice, comfortable, convenient!

Very smooth process with check in. The property was perfect and close to Disney World. Loved that Walmart was close by. We’re from Hawaii and we don’t wear shoes/slippers in the house but quickly found out that the floors were clean but not clean eno...

Makamae T.
Makamae T.
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy

How many holiday rentals are available around Windsor Hills Resort?

Our 2023 accommodation listings offer a large selection of 1,146 holiday lettings around Windsor Hills Resort. From 849 houses to 235 villas, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

Can I rent Houses near Windsor Hills Resort?

Yes, of course. Vrbo UK has 849 Houses near Windsor Hills Resort. Our other popular types of holiday rentals near Windsor Hills Resort include:

  • Villas: 235 holiday lettings
  • Townhouses: 186 holiday lettings
  • Flats: 297 holiday lettings

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

Can I find a holiday accommodation with pool near Windsor Hills Resort?

Yes, you can select your preferred holiday accommodation with pool among our 1,118 holiday rentals with pool available near Windsor Hills Resort. Please use our search bar to access the selection of self catering accommodations available.

Holiday rental ideas

Top Filters

Destinations you may also like