
Windsor at Westside vacation rentals
We found 988 vacation rentals — enter your dates for availability
Vacation rentals with weekly discounts - Windsor at Westside
Showing deals for:Oct 31 - Nov 7
Image gallery for 5Star Resort/Clean and Safe/Mins to Parks/WaterPark/Arcade/Bar/Gym/Golf/AC/WiFi

9.69.6 out of 10 rating
Exceptional
(47 reviews)
5Star Resort/Clean and Safe/Mins to Parks/WaterPark/Arcade/Bar/Gym/Golf/AC/WiFi
Kissimmee, FL
5% off
Price is $578
$578
$4,047 for 7 nights
$4,047 for 7 nights
All fees included
Image gallery for 9Br/6Ba luxurious Pool House with lake view from 280/nt, Close To Disney

8.28.2 out of 10 rating
Very Good
(18 reviews)
9Br/6Ba luxurious Pool House with lake view from 280/nt, Close To Disney
Kissimmee, FL
28% off
Price is $359
$359
$2,512 for 7 nights
$2,512 for 7 nights
All fees included
Image gallery for Cost-effective! 8bd/6ba pool house with lake view, close to Disney

9.09.0 out of 10 rating
Wonderful
(18 reviews)
Cost-effective! 8bd/6ba pool house with lake view, close to Disney
Kissimmee, FL
28% off
Price is $302
$302
$2,112 for 7 nights
$2,112 for 7 nights
All fees included
Image gallery for Fully Renovated! 5/4.5, Heated Pool, 9 mi. to Disney, Lazy River and Waterpark!

1010 out of 10 rating
Exceptional
(6 reviews)
Fully Renovated! 5/4.5, Heated Pool, 9 mi. to Disney, Lazy River and Waterpark!
Kissimmee, FL
8% off
Price is $293
$293
$2,049 for 7 nights
$2,049 for 7 nights
All fees included
Image gallery for Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/Spa/WiFI

8.48.4 out of 10 rating
Very Good
(65 reviews)
Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/Spa/WiFI
Kissimmee, FL
7% off
Price is $255
$255
$1,784 for 7 nights
$1,784 for 7 nights
All fees included
Image gallery for 🏝🏝🏝 Luxury Windsor Villa! Newly Furnished and Upgraded, Near Disney

9.69.6 out of 10 rating
Exceptional
(85 reviews)
🏝🏝🏝 Luxury Windsor Villa! Newly Furnished and Upgraded, Near Disney
Kissimmee, FL
8% off
Price is $416
$416
$2,914 for 7 nights
$2,914 for 7 nights
All fees included
Image gallery for Windsor Luxury 9Bd Villa South-facing Pool/Spa BBQ Game Room/3min Walk to club

9.29.2 out of 10 rating
Wonderful
(77 reviews)
Windsor Luxury 9Bd Villa South-facing Pool/Spa BBQ Game Room/3min Walk to club
Kissimmee, FL
8% off
Price is $380
$380
$2,661 for 7 nights
$2,661 for 7 nights
All fees included
Image gallery for Magical Theme Rooms, Water Park, Arcade, Sleep 18!

1010 out of 10 rating
Exceptional
(9 reviews)
Magical Theme Rooms, Water Park, Arcade, Sleep 18!
Kissimmee, FL
9% off
Price is $374
$374
$2,616 for 7 nights
$2,616 for 7 nights
All fees included
Image gallery for 8br/6ba pool villa with lake view, Near Disney

9.09.0 out of 10 rating
Wonderful
(11 reviews)
8br/6ba pool villa with lake view, Near Disney
Kissimmee, FL
28% off
Price is $322
$322
$2,251 for 7 nights
$2,251 for 7 nights
All fees included
Image gallery for Family Fun! ☀️ Private Heated Pool & Spa 4mi to Disney! 🦩

9.69.6 out of 10 rating
Exceptional
(18 reviews)
Family Fun! ☀️ Private Heated Pool & Spa 4mi to Disney! 🦩
Kissimmee, FL
8% off
Price is $536
$536
$3,752 for 7 nights
$3,752 for 7 nights
All fees included
Image gallery for Closest Units to Clubhouse/Waterpark - Beautiful Townhome 20 Minutes from Disney

9.89.8 out of 10 rating
Exceptional
(6 reviews)
Closest Units to Clubhouse/Waterpark - Beautiful Townhome 20 Minutes from Disney
Kissimmee, FL
9% off
Price is $209
$209
$1,465 for 7 nights
$1,465 for 7 nights
All fees included
Image gallery for NEW LUXURY LAKE FRONT VILLA. Hot Tub, Pool, Games Room, Windsor at Westside

9.29.2 out of 10 rating
Wonderful
(36 reviews)
NEW LUXURY LAKE FRONT VILLA. Hot Tub, Pool, Games Room, Windsor at Westside
Kissimmee, FL
8% off
Price is $486
$486
$3,405 for 7 nights
$3,405 for 7 nights
All fees included
Image gallery for Cost-effective!!! 9Br/6Ba Pool Villa with lake view,Near Disney

8.68.6 out of 10 rating
Excellent
(13 reviews)
Cost-effective!!! 9Br/6Ba Pool Villa with lake view,Near Disney
Kissimmee, FL
27% off
Price is $361
$361
$2,525 for 7 nights
$2,525 for 7 nights
All fees included
Image gallery for Stunning 5bd Retreat, Pool, BBQ & Game Room, Just 20min From Disney

9.29.2 out of 10 rating
Wonderful
(39 reviews)
Stunning 5bd Retreat, Pool, BBQ & Game Room, Just 20min From Disney
Kissimmee, FL
8% off
Price is $219
$219
$1,530 for 7 nights
$1,530 for 7 nights
All fees included
Image gallery for Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney

1010 out of 10 rating
Exceptional
(37 reviews)
Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
Kissimmee, FL
8% off
Price is $199
$199
$1,392 for 7 nights
$1,392 for 7 nights
All fees included
Image gallery for Amazing Themes | Luxury Villa | FREE Arcade & Theater

9.09.0 out of 10 rating
Wonderful
(8 reviews)
Amazing Themes | Luxury Villa | FREE Arcade & Theater
Kissimmee, FL
7% off
Price is $537
$537
$3,758 for 7 nights
$3,758 for 7 nights
All fees included
Image gallery for NEW OPENING! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~

9.29.2 out of 10 rating
Wonderful
(11 reviews)
NEW OPENING! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
Kissimmee, FL
8% off
Price is $222
$222
$1,557 for 7 nights
$1,557 for 7 nights
All fees included
Image gallery for Beautiful 6-bedroom house, themed rooms, game room, wi-fi, minutes from Disney

9.09.0 out of 10 rating
Wonderful
(24 reviews)
Beautiful 6-bedroom house, themed rooms, game room, wi-fi, minutes from Disney
Kissimmee, FL
8% off
Price is $438
$438
$3,068 for 7 nights
$3,068 for 7 nights
All fees included
Image gallery for New Opening! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~

9.09.0 out of 10 rating
Wonderful
(6 reviews)
New Opening! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
Kissimmee, FL
8% off
Price is $222
$222
$1,557 for 7 nights
$1,557 for 7 nights
All fees included
Image gallery for High cost performance!!! New 9 Br/6 Ba Pool Villa, Close To Disney

9.09.0 out of 10 rating
Wonderful
(70 reviews)
High cost performance!!! New 9 Br/6 Ba Pool Villa, Close To Disney
Kissimmee, FL
27% off
Price is $359
$359
$2,510 for 7 nights
$2,510 for 7 nights
All fees included
Image gallery for 5Star Resort/Contctless Checkin/Mins to Parks/WaterPark/Arcade/Bar/Gym/AC/WiFi

8.68.6 out of 10 rating
Excellent
(27 reviews)
5Star Resort/Contctless Checkin/Mins to Parks/WaterPark/Arcade/Bar/Gym/AC/WiFi
Kissimmee, FL
6% off
Price is $493
$493
$3,449 for 7 nights
$3,449 for 7 nights
All fees included
Image gallery for High cost performance!!! 9Br/6Ba Pool Villa, Close To Disney

8.68.6 out of 10 rating
Excellent
(7 reviews)
High cost performance!!! 9Br/6Ba Pool Villa, Close To Disney
Kissimmee, FL
27% off
Price is $355
$355
$2,482 for 7 nights
$2,482 for 7 nights
All fees included
Image gallery for Resort-style Lazy River! 9Br/6Ba lake view Pool House, Close to Disney

8.68.6 out of 10 rating
Excellent
(10 reviews)
Resort-style Lazy River! 9Br/6Ba lake view Pool House, Close to Disney
Kissimmee, FL
25% off
Price is $378
$378
$2,644 for 7 nights
$2,644 for 7 nights
All fees included
Image gallery for 8br/6ba pool villa, Close to Disney,Resort-style heated Pool and Lazy River

8.48.4 out of 10 rating
Very Good
(5 reviews)
8br/6ba pool villa, Close to Disney,Resort-style heated Pool and Lazy River
Kissimmee, FL
27% off
Price is $339
$339
$2,375 for 7 nights
$2,375 for 7 nights
All fees included
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Find the best place to stay - Windsor at Westside
Showing deals for: Oct 31 - Nov 3Dream House Facing South with Lake View Next Disney World - Windsor at Westside
Sleeps 10 · 4 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
The current price is $221
$221
$663 for 3 nights
All fees included
Modern Spacious Villa with No Rear Neighbors! Game Room, BBQ Grill, Kid Themed Bedrooms, Free Wi-Fi!
Sleeps 14 · 5 bedrooms · 5 bathrooms
8.88.8 out of 10
Excellentexcellent
38 reviews(38 reviews)
The current price is $289
$289
$868 for 3 nights
All fees included
[New Opening] 5b4b BBQ&HeatPool. Themed Rooms; Next to Disney
Sleeps 12 · 5 bedrooms · 4+ bathrooms
6.66.6 out of 10
7 reviews(7 reviews)
The current price is $238
$238
$715 for 3 nights
All fees included
6BR Villa with Pool in Windsor at Westside Resort, Near Disney World
Sleeps 15 · 6 bedrooms · 4+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
72 reviews(72 reviews)
The current price is $306
$306
$918 for 3 nights
All fees included
Townhouse in Kissimmee Your perfect family getaway Fits up to 15 people! 4ba4be
Sleeps 14 · 5 bedrooms · 4+ bathrooms
8.08.0 out of 10
Very Goodvery good
17 reviews(17 reviews)
The current price is $248
$248
$744 for 3 nights
All fees included
Home 8 Bdrm at Windsor Westside with Top Amenities
Sleeps 18 · 8 bedrooms · 6 bathrooms
6.06.0 out of 10
1 review(1 review)
The current price is $392
$392
$1,176 for 3 nights
All fees included
Top rated rentals - Windsor at Westside
In a galaxy far- far away
1010 out of 10
Exceptionalexceptional
1 review(1 review)
The Star Wars theme was beautifully executed. Everything was a great experience. The heated pool was the cherry on top.
Aswin W.
Stayed Jun 2025
Great stay
1010 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
Perfect for families
David S.
Stayed Jun 2025
Incredible!
1010 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
We had an incredible stay! The townhouse was perfect. It was incredibly clean and had everything we needed. Having the pool made the mornings and evenings after visiting Disney all day just so nice and relaxing! We will definitely look to rent here again when we are back in Florida!
Cara R.
Stayed May 2025
Family Mini Vacay.
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Very spacious house, clean, very nice view of the lake.
Sarina M.
Stayed May 2025
Wonder Spring Break Week
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
The townhouse was accurately described and exceeded our expectations. Totally worth the additional fee to heat the private pool. Great location in the neighborhood as a corner unit with a grassy area making the space feel so much bigger and still private. Very comfortable mattresses on the beds made for restful sleep time after time spent at Universal Studios. Easy access to Disney World locations as well. Publix was only a few minutes away for us to stick up with groceries for the week. Totally worth the value to rent a cabana at the clubhouse-water park. Our grandsons had a wonderful time at the community pool and Lazy River as well as our private pool. Extra bonus board games for family fun in the evenings too!We will definitely keep this unit in mind for our next trip to the Orlando area!
Marybeth S.
Stayed Mar 2025
Wonderful place to stay
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Everything was good, the house is big and clean. The only thing is that if you need the pool to be heated you need to pay a very high price per day in advanced; and I only noticed this after I reserved and trying to get the payment didn’t work, so I gave up. We didn’t use the pool, that was a big decision point in booking.
Artemis !.
Stayed Feb 2025
Disney Family Vacay
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
We love Windsor at Westside resort so conveniently located near the parks. The host was so helpful during our stay. The house was beautiful, and the hot tub was a favorite. The themed rooms made it atheistically pleasing and the game room was a hit for the Teens. We will definitely stay here again!
Mykeva F.
Stayed Nov 2024
Great house - very clean and responsive host!
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
We were 2 families with 10 people. The house was very clean and the host responded to all our messages. Arrival was super easy. The boys loved the pool and game room. We don’t have any complaints!
Jamie W.
Stayed Nov 2024