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Windsor at Westside, Kissimmee, Florida, United States of America

Windsor at Westside holiday homes

We found 986 holiday rentals — enter your dates for availability

Discover a selection of 1,000 holiday homes in Windsor at Westside that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Bookabach holiday homes have the best amenities for hanging out with the people that matter most, including private pool and pool. Prices start at NZ$ 372 per night, and holiday houses and villas are popular options for a stay in Windsor at Westside. Either way, you'll find accommodation for everyone's needs.
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Find the best place to stay — Windsor at Westside

❤️❤️Steps to Clubhouse,Spacious Villa with Pool/Spa, NEW Design **Lake Front**

Sleeps 20 · 8 Bedrooms · 6 Bathrooms
NZ$ 635 avg/night
(24)

NEW LUXURY Villa- across the street from the club house. Minutes to Disney.

Sleeps 16 · 8 Bedrooms · 6 Bathrooms
NZ$ 683 avg/night
(20)

😎Popular Luxury Resort Home, Private Pool, 10 Minutes From Disney!☀️

Sleeps 14 · 6 Bedrooms · 4 Bathrooms
NZ$ 490 avg/night
(79)

New Luxury Villa, with Private Pool, Hot Tub, Pool Table, 10 Minutes to Disney!

Sleeps 17 · 8 Bedrooms · 6 Bathrooms
NZ$ 610 avg/night
(87)

Beautiful House with Private Lakeview Pool, Hot Tub, Pool Table, Foosball, Wifi!

Sleeps 24 · 9 Bedrooms · 6 Bathrooms
NZ$ 715 avg/night
(43)

Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/Spa/WiFI

Sleeps 18 · 7 Bedrooms · 5 Bathrooms
NZ$ 622 avg/night
(41)

Search 986 holiday rentals

Top rated rentals — Windsor at Westside
Stayed May 2021

Beautiful house in the perfect location

This house has everything that your large group will need, plus it is very close to the parks and plenty of restaurant options. I had a large group of 11 adults staying here and there were plenty of places to spread out to, so that we did not feel li...

Clay M.
Clay M.

Charlotte, NC

Stayed May 2021

Disney vacation

Great proximity to all disney parks. Great 9 bedroom 6 bathroom home. It was great for our first family trip. Frank answered all our questions and Jeeves helped us with the few requests we had. Gated entry was in the process of renovation, so it caus...

Rhodalyn R.
Rhodalyn R.
Stayed Apr 2021

Great Vacation Home

House was perfect! Have 15 people in total with kids. The house was extremely clean and had everything needed during our stay. Location is close to all parks and near all stores for any items needed. The only thing is that the wifi is slow. But to be...

Luisana C.
Luisana C.
Stayed Apr 2021

Orlando getaway

This house had plenty of space for our 2 families that shared the house. I highly recommend paying to heat the pool and spa, even though it was hot during our trip it made for fun night swims. The King size beds were comfortable. The game room was no...

Amanda W.
Amanda W.
Stayed Apr 2021

Amazing home away from home ❤

Let me start off by saying Me & my Family are already planning our next trip to Florida and have already said we want this Same House, we had everything we needed and more. The kids loved the pool & hot tub never left it. Cleanliness was 💯 If your l...

Christin S.
Christin S.
Stayed Apr 2021

Family vacation 2021

This condo was located in a gated community and just what we were looking for 2 families. It was plenty big and clean. It is close to Disney and Universal is about 30 minutes away. We had paid a fee to have the pool heated and it was great for night ...

Raina M.
Raina M.
Stayed Apr 2021

Perfect Home for a Family Gathering

We had a property owner on a different location cancel on us 2 days before arrival! These owners bent over backward to help us out and let us stay last minute. Our vacation was saved! We had plenty of room to play and enjoy our stay with our cousins....

Shlori D.
Shlori D.
Stayed Apr 2021

Just what we needed!

This house is gorgeous! Extremely well stocked with all we needed to hunker down and prepare yummy meals. The beds were super comfy and the lanai is the perfect place to gather and chat or just sit quietly and read a book. Pat and her management team...

Sandie D.
Sandie D.

Vineyard Haven

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How many holiday homes are available around Windsor at Westside?

Our 2021 holiday accommodation listings offer a large selection of 986 holiday rentals around Windsor at Westside. From 975 holiday houses to 337 villas, find unique holiday house for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.