Windsor at Westside vacation rentals
We found 993 vacation rentals — enter your dates for availability
Vacation rentals with weekly discounts - Windsor at Westside
Showing deals for:Sep 12 - Sep 19
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
(72 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 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
Price is $500
$500
$3,498 for 7 nights
$3,498 for 7 nights
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
Price is $362
$362
$2,535 for 7 nights
$2,535 for 7 nights
All fees included
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
Price is $348
$348
$2,437 for 7 nights
$2,437 for 7 nights
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
Price is $251
$251
$1,756 for 7 nights
$1,756 for 7 nights
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
Price is $225
$225
$1,573 for 7 nights
$1,573 for 7 nights
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
(13 reviews)
Townhouse in Kissimmee Your perfect family getaway Fits up to 15 people! 4ba4be
Kissimmee, FL
12% off
Price is $182
$182
$1,277 for 7 nights
$1,277 for 7 nights
All fees included
Image gallery for Waterfront Luxury, 8-bedroom Villa w/ Private Pool - 15 mins from Disney World
9.69.6 out of 10 rating
Exceptional
(141 reviews)
Waterfront Luxury, 8-bedroom Villa w/ Private Pool - 15 mins from Disney World
Kissimmee, FL
8% off
Price is $470
$470
$3,288 for 7 nights
$3,288 for 7 nights
All fees included
Image gallery for 15 min from Disney - Only steps away from Huge Pool, Clubhouse, Waterpark
9.69.6 out of 10 rating
Exceptional
(5 reviews)
15 min from Disney - Only steps away from Huge Pool, Clubhouse, Waterpark
Kissimmee, FL
8% off
Price is $184
$184
$1,291 for 7 nights
$1,291 for 7 nights
All fees included
Image gallery for Spring Break Dates Still Available!
1010 out of 10 rating
Exceptional
(24 reviews)
Spring Break Dates Still Available!
Kissimmee, FL
8% off
Price is $308
$308
$2,157 for 7 nights
$2,157 for 7 nights
All fees included
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
Price is $369
$369
$2,581 for 7 nights
$2,581 for 7 nights
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
(117 reviews)
Luxury Villa Pool/HotTub/Karaoke 7B Windsor Westside Resort,Disney,Kissimmee
Kissimmee, FL
8% off
Price is $372
$372
$2,604 for 7 nights
$2,604 for 7 nights
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
9% off
Price is $187
$187
$1,310 for 7 nights
$1,310 for 7 nights
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
Price is $240
$240
$1,681 for 7 nights
$1,681 for 7 nights
All fees included
Image gallery for Fun Paradise in Kissimmee
1010 out of 10 rating
Exceptional
(7 reviews)
Fun Paradise in Kissimmee
Kissimmee, FL
8% off
Price is $322
$322
$2,254 for 7 nights
$2,254 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
(32 reviews)
Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
Kissimmee, FL
15% off
Price is $183
$183
$1,279 for 7 nights
$1,279 for 7 nights
All fees included
Image gallery for Sleeps 20! Resort Home Near Disney, Pool+Game Room | Twice-as-Nice by AvantStay
1010 out of 10 rating
Exceptional
(6 reviews)
Sleeps 20! Resort Home Near Disney, Pool+Game Room | Twice-as-Nice by AvantStay
Kissimmee, Florida
6% off
Price is $380
$380
$2,659 for 7 nights
$2,659 for 7 nights
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
(7 reviews)
NEW OPENING! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
Kissimmee, FL
9% off
Price is $187
$187
$1,310 for 7 nights
$1,310 for 7 nights
All fees included
Image gallery for Villa w/ Heated pool & FREE Waterpark near Disney
8.88.8 out of 10 rating
Excellent
(5 reviews)
Villa w/ Heated pool & FREE Waterpark near Disney
Kissimmee, Florida
15% off
Price is $306
$306
$2,145 for 7 nights
$2,145 for 7 nights
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
Price is $220
$220
$1,539 for 7 nights
$1,539 for 7 nights
All fees included
Image gallery for Comfortable Vacation Home - Great Resort | Pool/Spa | Sleeps 20 | WW101
9.09.0 out of 10 rating
Wonderful
(18 reviews)
Comfortable Vacation Home - Great Resort | Pool/Spa | Sleeps 20 | WW101
Kissimmee, FL
7% off
Price is $406
$406
$2,844 for 7 nights
$2,844 for 7 nights
All fees included
Image gallery for Spacious Home with Pvt Pool and Resort Amenities. Perfect for Disney Getaways!
9.09.0 out of 10 rating
Wonderful
(31 reviews)
Spacious Home with Pvt Pool and Resort Amenities. Perfect for Disney Getaways!
Kissimmee, FL
15% off
Price is $237
$237
$1,658 for 7 nights
$1,658 for 7 nights
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
Price is $326
$326
$2,281 for 7 nights
$2,281 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
$2,915 for 7 nights
$2,915 for 7 nights
All fees included
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)
Windsor @ Westside 5 Bed, Private townhouse, Private Pool, Wonderful Amenities
Sleeps 10 · 5 bedrooms · 4+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
89 reviews(89 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)
Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/Spa/WiFI
Sleeps 18 · 7 bedrooms · 5+ bathrooms
8.68.6 out of 10
Excellentexcellent
64 reviews(64 reviews)
Family-Friendly Townhouse w/ Private Pool & Patio Kitchen across from Clubhouse
Sleeps 9 · 4 bedrooms · 3+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
40 reviews(40 reviews)
Sleeps 20! Resort Home Near Disney, Pool+Game Room | Twice-as-Nice by AvantStay
Sleeps 20 · 8 bedrooms · 6 bathrooms
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Top rated rentals - Windsor at Westside
everything was great
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Best accommodation in 22 days
1010 out of 10
Exceptionalexceptional
10 reviews(10 reviews)
Incredible!
1010 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
Overall great!
1010 out of 10
Exceptionalexceptional
32 reviews(32 reviews)
More than you can expect!
1010 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
Perfect location
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Great quick stay
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Orlando family trip
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
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All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
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