Windsor at Westside holiday homes
We found 995 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor at Westside
Showing deals for:15 Aug - 22 Aug
Image gallery for Stunning 5 bed/5 bath pool home, games room, beautiful resort, Disney 8 miles!
9.89.8 out of 10 rating
Exceptional
(22 reviews)
Stunning 5 bed/5 bath pool home, games room, beautiful resort, Disney 8 miles!
Kissimmee, FL
5% off
Price is NZ$4,283
NZ$4,283
NZ$612 per night
includes taxes & fees
Image gallery for Stylish Resort Townhome near Disney
1010 out of 10 rating
Exceptional
(16 reviews)
Stylish Resort Townhome near Disney
Kissimmee, FL
11% off
Price is NZ$2,832
NZ$2,832
NZ$405 per night
includes taxes & fees
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
7% off
Price is NZ$5,152
NZ$5,152
NZ$736 per night
includes taxes & fees
Image gallery for Luxury Villa!! 8Br/6Ba Resort-Villa-Pool-Near Disney, 10% weekly discount!!
9.89.8 out of 10 rating
Exceptional
(49 reviews)
Luxury Villa!! 8Br/6Ba Resort-Villa-Pool-Near Disney, 10% weekly discount!!
Kissimmee, FL
7% off
Price is NZ$4,693
NZ$4,693
NZ$670 per night
includes taxes & fees
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
11% off
Price is NZ$4,672
NZ$4,672
NZ$667 per night
includes taxes & fees
Image gallery for Spring Break Dates Still Available!
1010 out of 10 rating
Exceptional
(23 reviews)
Spring Break Dates Still Available!
Kissimmee, FL
7% off
Price is NZ$4,470
NZ$4,470
NZ$639 per night
includes taxes & fees
Image gallery for 6BR Villa with Pool in Windsor at Westside Resort, Near Disney World
9.69.6 out of 10 rating
Exceptional
(68 reviews)
6BR Villa with Pool in Windsor at Westside Resort, Near Disney World
Kissimmee, FL
10% off
Price is NZ$3,384
NZ$3,384
NZ$483 per night
includes taxes & fees
Image gallery for Waterfront Luxury, 8-bedroom Villa w/ Private Pool - 15 mins from Disney World
9.69.6 out of 10 rating
Exceptional
(139 reviews)
Waterfront Luxury, 8-bedroom Villa w/ Private Pool - 15 mins from Disney World
Kissimmee, FL
7% off
Price is NZ$6,169
NZ$6,169
NZ$881 per night
includes taxes & fees
Image gallery for Fun Paradise in Kissimmee
1010 out of 10 rating
Exceptional
(7 reviews)
Fun Paradise in Kissimmee
Kissimmee, FL
7% off
Price is NZ$4,251
NZ$4,251
NZ$607 per night
includes taxes & fees
Image gallery for Luxury Villa Pool/HotTub/Karaoke 7B Windsor Westside Resort,Disney,Kissimmee
9.69.6 out of 10 rating
Exceptional
(115 reviews)
Luxury Villa Pool/HotTub/Karaoke 7B Windsor Westside Resort,Disney,Kissimmee
Kissimmee, FL
7% off
Price is NZ$4,886
NZ$4,886
NZ$698 per night
includes taxes & fees
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 NZ$2,648
NZ$2,648
NZ$378 per night
includes taxes & fees
Image gallery for Stunning 5bd Retreat, Pool, BBQ & Game Room, Just 20min From Disney
9.29.2 out of 10 rating
Wonderful
(35 reviews)
Stunning 5bd Retreat, Pool, BBQ & Game Room, Just 20min From Disney
Kissimmee, FL
6% off
Price is NZ$3,380
NZ$3,380
NZ$483 per night
includes taxes & fees
Image gallery for 5BD/4.5BA home, 9 mi. from Disney, Free Access to Lazy River and Waterpark!
1010 out of 10 rating
Exceptional
(6 reviews)
5BD/4.5BA home, 9 mi. from Disney, Free Access to Lazy River and Waterpark!
Kissimmee, FL
7% off
Price is NZ$3,700
NZ$3,700
NZ$529 per night
includes taxes & fees
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
7% off
Price is NZ$4,317
NZ$4,317
NZ$617 per night
includes taxes & fees
Image gallery for Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
9.89.8 out of 10 rating
Exceptional
(29 reviews)
Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
Kissimmee, FL
6% off
Price is NZ$3,050
NZ$3,050
NZ$436 per night
includes taxes & fees
Image gallery for Private Pool,Lazy River & Tiki Bar Fun Near Disney
8.88.8 out of 10 rating
Excellent
(6 reviews)
Private Pool,Lazy River & Tiki Bar Fun Near Disney
Kissimmee, Florida
7% off
Price is NZ$2,958
NZ$2,958
NZ$423 per night
includes taxes & fees
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
(11 reviews)
Townhouse in Kissimmee Your perfect family getaway Fits up to 15 people! 4ba4be
Kissimmee, FL
10% off
Price is NZ$2,450
NZ$2,450
NZ$350 per night
includes taxes & fees
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
6% off
Price is NZ$3,898
NZ$3,898
NZ$557 per night
includes taxes & fees
Image gallery for Spacious 8-bedroom house in beautiful Kissimmee with WiFi, AC
1010 out of 10 rating
Exceptional
(62 reviews)
Spacious 8-bedroom house in beautiful Kissimmee with WiFi, AC
Kissimmee, FL
18% off
Price is NZ$4,007
NZ$4,007
NZ$572 per night
includes taxes & fees
Image gallery for Disney Themed 5BR - Pool, Arcade, PS5,Xbox, Sleeps 16+, minutes to Disney Parks
1010 out of 10 rating
Exceptional
(58 reviews)
Disney Themed 5BR - Pool, Arcade, PS5,Xbox, Sleeps 16+, minutes to Disney Parks
Kissimmee, FL
7% off
Price is NZ$2,649
NZ$2,649
NZ$378 per night
includes taxes & fees
Image gallery for 5Star Resort/Contctless Checkin/Mins to Parks/WaterPark/Arcade/Bar/Gym/AC/WiFi
8.68.6 out of 10 rating
Excellent
(26 reviews)
5Star Resort/Contctless Checkin/Mins to Parks/WaterPark/Arcade/Bar/Gym/AC/WiFi
Kissimmee, FL
7% off
Price is NZ$6,541
NZ$6,541
NZ$934 per night
includes taxes & fees
Image gallery for Beautiful South Facing Lake View 8BR/6BA, Custom Furniture
1010 out of 10 rating
Exceptional
(39 reviews)
Beautiful South Facing Lake View 8BR/6BA, Custom Furniture
Kissimmee, FL
16% off
Price is NZ$4,308
NZ$4,308
NZ$615 per night
includes taxes & fees
Image gallery for ⭐️⭐️⭐️⭐️⭐️ Beautiful 9Bed/6Bath, Disney & Universal nearby and fun amenities!
9.49.4 out of 10 rating
Exceptional
(73 reviews)
⭐️⭐️⭐️⭐️⭐️ Beautiful 9Bed/6Bath, Disney & Universal nearby and fun amenities!
Kissimmee, FL
7% off
Price is NZ$5,233
NZ$5,233
NZ$748 per night
includes taxes & fees
Image gallery for Escape in Style: Game Room, Pvt Pool, gated community & Resort amenities Await
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Escape in Style: Game Room, Pvt Pool, gated community & Resort amenities Await
Kissimmee, FL
6% off
Price is NZ$3,585
NZ$3,585
NZ$512 per night
includes taxes & fees
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)
Dream House Facing South with Lake View Next Disney World - Windsor at Westside
Sleeps 10 · 4 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
12 reviews(12 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
4 reviews(4 reviews)
Windsor @ Westside 5 Bed, Private townhouse, Private Pool, Wonderful Amenities
Sleeps 10 · 5 bedrooms · 4+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
88 reviews(88 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
63 reviews(63 reviews)
Nice Villa- Private Pool/Spa, Free Resort Access!
Sleeps 14 · 7 bedrooms · 5+ bathrooms
9.09.0 out of 10
Wonderfulwonderful
14 reviews(14 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value