Windsor at Westside vacation rentals
We found 975 vacation rentals — enter your dates for availability
Vacation rentals with weekly discounts - Windsor at Westside
Showing deals for:Oct 3 - Oct 10
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
$2,189 for 7 nights
$2,189 for 7 nights
Price is $313
$313
Fees included upfront
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
$2,985 for 7 nights
$2,985 for 7 nights
Price is $426
$426
Fees included upfront
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
$2,242 for 7 nights
$2,242 for 7 nights
Price is $320
$320
Fees included upfront
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
$2,915 for 7 nights
$2,915 for 7 nights
Price is $416
$416
Fees included upfront
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
$1,756 for 7 nights
$1,756 for 7 nights
Price is $251
$251
Fees included upfront
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
Fees included upfront
Image gallery for Windsor Luxury 9Bd Villa South-facing Pool/Spa BBQ Game Room/3min Walk to club
9.49.4 out of 10 rating
Exceptional
(75 reviews)
Windsor Luxury 9Bd Villa South-facing Pool/Spa BBQ Game Room/3min Walk to club
Kissimmee, FL
8% off
$2,661 for 7 nights
$2,661 for 7 nights
Price is $380
$380
Fees included upfront
Image gallery for Magical Theme Rooms, Water Park, Arcade, Sleep 18!
1010 out of 10 rating
Exceptional
(7 reviews)
Magical Theme Rooms, Water Park, Arcade, Sleep 18!
Kissimmee, FL
9% off
$2,535 for 7 nights
$2,535 for 7 nights
Price is $362
$362
Fees included upfront
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
$3,498 for 7 nights
$3,498 for 7 nights
Price is $500
$500
Fees included upfront
Image gallery for Spring Break Dates Still Available!
1010 out of 10 rating
Exceptional
(26 reviews)
Spring Break Dates Still Available!
Kissimmee, FL
8% off
$2,336 for 7 nights
$2,336 for 7 nights
Price is $334
$334
Fees included upfront
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
(8 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
Fees included upfront
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
Fees included upfront
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
Fees included upfront
Image gallery for Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
1010 out of 10 rating
Exceptional
(33 reviews)
Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
Kissimmee, FL
15% off
$1,303 for 7 nights
$1,303 for 7 nights
Price is $186
$186
Fees included upfront
Image gallery for Sleeps 20! Resort Home Near Disney, Pool+Game Room | Twice-as-Nice by AvantStay
1010 out of 10 rating
Exceptional
(7 reviews)
Sleeps 20! Resort Home Near Disney, Pool+Game Room | Twice-as-Nice by AvantStay
Kissimmee, Florida
6% off
$2,620 for 7 nights
$2,620 for 7 nights
Price is $374
$374
Fees included upfront
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
Fees included upfront
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
15% off
$1,425 for 7 nights
$1,425 for 7 nights
Price is $204
$204
Fees included upfront
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
$1,197 for 7 nights
$1,197 for 7 nights
Price is $171
$171
Fees included upfront
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
$1,681 for 7 nights
$1,681 for 7 nights
Price is $240
$240
Fees included upfront
Image gallery for Game Room | Private Pool | Gym | 19 Mins to Disney
8.48.4 out of 10 rating
Very Good
(14 reviews)
Game Room | Private Pool | Gym | 19 Mins to Disney
Kissimmee, Florida
8% off
$2,437 for 7 nights
$2,437 for 7 nights
Price is $348
$348
Fees included upfront
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
$2,281 for 7 nights
$2,281 for 7 nights
Price is $326
$326
Fees included upfront
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
$2,050 for 7 nights
$2,050 for 7 nights
Price is $293
$293
Fees included upfront
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
Fees included upfront
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
(15 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
Fees included upfront
Find spaces that suit your style
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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
92 reviews(92 reviews)
Windsor at Westside Home with Private pool!!
Sleeps 10 · 5 bedrooms · 4+ bathrooms
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)
[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)
Top rated rentals - Windsor at Westside
Nice house, enjoyed our stay
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Perfect Home for a Short Getaway!
1010 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
Amazing Accomodations!
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Great place to stay
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Incredible!
1010 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
Overall great!
1010 out of 10
Exceptionalexceptional
33 reviews(33 reviews)
Family trip
1010 out of 10
Exceptionalexceptional
1 review(1 review)
More than you can expect!
1010 out of 10
Exceptionalexceptional
17 reviews(17 reviews)