
Windsor at Westside vacation rentals
We found 1,000 vacation rentals — enter your dates for availability
Vacation rentals with weekly discounts - Windsor at Westside
Showing deals for:Oct 17 - Oct 24
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
$2,136 for 7 nights
$2,136 for 7 nights
Price is $305
$305
All fees included
Image gallery for 6BR Villa with Pool in Windsor at Westside Resort, Near Disney World

9.69.6 out of 10 rating
Exceptional
(72 reviews)
6BR Villa with Pool in Windsor at Westside Resort, Near Disney World
Kissimmee, FL
11% off
$1,757 for 7 nights
$1,757 for 7 nights
Price is $251
$251
All fees included
Image gallery for Your next vacation home at Windsor at Westside, South Facing Pool/Spa, Game Rm

9.89.8 out of 10 rating
Exceptional
(30 reviews)
Your next vacation home at Windsor at Westside, South Facing Pool/Spa, Game Rm
Kissimmee, FL
5% off
$2,750 for 7 nights
$2,750 for 7 nights
Price is $393
$393
All fees included
Image gallery for Luxury Villa Pool/HotTub/Karaoke 7B Windsor Westside Resort,Disney,Kissimmee

9.69.6 out of 10 rating
Exceptional
(118 reviews)
Luxury Villa Pool/HotTub/Karaoke 7B Windsor Westside Resort,Disney,Kissimmee
Kissimmee, FL
8% off
$2,604 for 7 nights
$2,604 for 7 nights
Price is $372
$372
All fees included
Image gallery for Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/Spa/WiFI

8.68.6 out of 10 rating
Excellent
(64 reviews)
Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/Spa/WiFI
Kissimmee, FL
7% off
$2,255 for 7 nights
$2,255 for 7 nights
Price is $322
$322
All fees included
Image gallery for Luxury Villa!! 8Br/6Ba Resort-Villa-Pool-Near Disney, 10% weekly discount!!

9.89.8 out of 10 rating
Exceptional
(51 reviews)
Luxury Villa!! 8Br/6Ba Resort-Villa-Pool-Near Disney, 10% weekly discount!!
Kissimmee, FL
7% off
$2,339 for 7 nights
$2,339 for 7 nights
Price is $334
$334
All fees included
Image gallery for Modern home away from home, South Facing Pool/Spa, Game Rm

9.89.8 out of 10 rating
Exceptional
(69 reviews)
Modern home away from home, South Facing Pool/Spa, Game Rm
Kissimmee, FL
5% off
$2,544 for 7 nights
$2,544 for 7 nights
Price is $363
$363
All fees included
Image gallery for Magical Theme Rooms, Water Park, Arcade, Sleep 18!

1010 out of 10 rating
Exceptional
(8 reviews)
Magical Theme Rooms, Water Park, Arcade, Sleep 18!
Kissimmee, FL
9% off
$2,560 for 7 nights
$2,560 for 7 nights
Price is $366
$366
All fees included
Image gallery for RENOVATED VILLA@WINDSOR@WESTSIDE !! Private Pool&Spa, ❤Mins2Disney❤A/C game room

1010 out of 10 rating
Exceptional
(27 reviews)
RENOVATED VILLA@WINDSOR@WESTSIDE !! Private Pool&Spa, ❤Mins2Disney❤A/C game room
Kissimmee, FL
12% off
$3,019 for 7 nights
$3,019 for 7 nights
Price is $431
$431
All fees included
Image gallery for Sun, Fun & Weekly Savings! Family-Pet Retreat w/ Pool + 5★ Clubhouse!

9.89.8 out of 10 rating
Exceptional
(46 reviews)
Sun, Fun & Weekly Savings! Family-Pet Retreat w/ Pool + 5★ Clubhouse!
Kissimmee, FL
8% off
$3,499 for 7 nights
$3,499 for 7 nights
Price is $500
$500
All fees included
Image gallery for New Opening! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~

9.69.6 out of 10 rating
Exceptional
(5 reviews)
New Opening! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
Kissimmee, FL
8% off
$1,557 for 7 nights
$1,557 for 7 nights
Price is $222
$222
All fees included
Image gallery for Closest Units to Clubhouse/Waterpark - Beautiful Townhome 20 Minutes from Disney

9.69.6 out of 10 rating
Exceptional
(5 reviews)
Closest Units to Clubhouse/Waterpark - Beautiful Townhome 20 Minutes from Disney
Kissimmee, FL
9% off
$1,483 for 7 nights
$1,483 for 7 nights
Price is $212
$212
All fees included
Image gallery for NEW OPENING! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~

9.49.4 out of 10 rating
Exceptional
(9 reviews)
NEW OPENING! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
Kissimmee, FL
8% off
$1,557 for 7 nights
$1,557 for 7 nights
Price is $222
$222
All fees included
Image gallery for Luxury Family Resort Vacation Home

9.89.8 out of 10 rating
Exceptional
(9 reviews)
Luxury Family Resort Vacation Home
Kissimmee, FL
5% off
$1,574 for 7 nights
$1,574 for 7 nights
Price is $225
$225
All fees included
Image gallery for 24 HOUR FLASH SALE - 5 STAR DISNEY VACATION HOME

9.49.4 out of 10 rating
Exceptional
(57 reviews)
24 HOUR FLASH SALE - 5 STAR DISNEY VACATION HOME
Kissimmee, FL
8% off
$2,281 for 7 nights
$2,281 for 7 nights
Price is $326
$326
All fees included
Image gallery for Windsor Fairytale is a 7 Bed Condo w/ pull-out sofa minutes from Disney!

1010 out of 10 rating
Exceptional
(9 reviews)
Windsor Fairytale is a 7 Bed Condo w/ pull-out sofa minutes from Disney!
Kissimmee, FL
8% off
$2,282 for 7 nights
$2,282 for 7 nights
Price is $326
$326
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
$3,405 for 7 nights
$3,405 for 7 nights
Price is $486
$486
All fees included
Image gallery for Luxury 5 Beds Villa with Private Pool - Carefully Sanitized - 8843 GC

9.29.2 out of 10 rating
Wonderful
(39 reviews)
Luxury 5 Beds Villa with Private Pool - Carefully Sanitized - 8843 GC
Kissimmee, FL
6% off
$1,196 for 7 nights
$1,196 for 7 nights
Price is $171
$171
All fees included
Image gallery for Resort-Style Stay | Private Pool, Lazy River & Gym

8.88.8 out of 10 rating
Excellent
(6 reviews)
Resort-Style Stay | Private Pool, Lazy River & Gym
Kissimmee, Florida
8% off
$1,680 for 7 nights
$1,680 for 7 nights
Price is $240
$240
All fees included
Image gallery for Family Paradise Near Disney - Private Pool, Game Room, Themed Suites

8.08.0 out of 10 rating
Very Good
(5 reviews)
Family Paradise Near Disney - Private Pool, Game Room, Themed Suites
Kissimmee, FL
15% off
$1,539 for 7 nights
$1,539 for 7 nights
Price is $220
$220
All fees included
Image gallery for Villa w/ Heated pool & FREE Waterpark near Disney

8.08.0 out of 10 rating
Very Good
(6 reviews)
Villa w/ Heated pool & FREE Waterpark near Disney
Kissimmee, Florida
15% off
$2,061 for 7 nights
$2,061 for 7 nights
Price is $294
$294
All fees included
Image gallery for Townhouse in Kissimmee Your perfect family getaway Fits up to 15 people! 4ba4be

8.08.0 out of 10 rating
Very Good
(16 reviews)
Townhouse in Kissimmee Your perfect family getaway Fits up to 15 people! 4ba4be
Kissimmee, FL
12% off
$1,277 for 7 nights
$1,277 for 7 nights
Price is $182
$182
All fees included
Image gallery for 9035 Amazing 5BD Family Home!

8.68.6 out of 10 rating
Excellent
(14 reviews)
9035 Amazing 5BD Family Home!
Kissimmee, FL
7% off
$1,605 for 7 nights
$1,605 for 7 nights
Price is $229
$229
All fees included
Image gallery for Spacious 5-bedroom Town home Pvt Pool, BBQ & Free Water Park Access Near Disney

9.89.8 out of 10 rating
Exceptional
(11 reviews)
Spacious 5-bedroom Town home Pvt Pool, BBQ & Free Water Park Access Near Disney
Kissimmee, FL
15% off
$1,399 for 7 nights
$1,399 for 7 nights
Price is $200
$200
All fees included
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Find the best place to stay - Windsor at Westside
Cozy Family Villa 5BR Pool Spa Near Disney ,8
Sleeps 11 · 5 bedrooms · 4 bathrooms
5.05.0 out of 10
2 reviews(2 reviews)
5BR Home w/ Pool - Windsor at Westside (8890GC)
Sleeps 13 · 5 bedrooms · 4+ bathrooms
7.87.8 out of 10
Goodgood
52 reviews(52 reviews)
Windsor @ Westside 5 Bed, Private townhouse, Private Pool, Wonderful Amenities
Sleeps 10 · 5 bedrooms · 4+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
93 reviews(93 reviews)
Windsor at Westside Home with Private pool!!
Sleeps 10 · 5 bedrooms · 4+ bathrooms
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)
Dream 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)
Top rated rentals - Windsor at Westside
Great stay
1010 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
Perfect for families
David S.
Stayed Jun 2025
Nice place
1010 out of 10
Exceptionalexceptional
1 review(1 review)
It was a nice house just difficult to find
David M.
Stayed May 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
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value