Windsor at Westside holiday rentals
We found 1,000 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor at Westside
Showing deals for:29 Aug - 5 Sept
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 S$3,752
S$3,752
S$536 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 S$4,255
S$4,255
S$608 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 S$3,622
S$3,622
S$517 per night
includes taxes & fees
Image gallery for Resort like: Pool, BBQ, Xbox & Club Access with Lazy River – 15 Min to Disney!
9.69.6 out of 10 rating
Exceptional
(20 reviews)
Resort like: Pool, BBQ, Xbox & Club Access with Lazy River – 15 Min to Disney!
Kissimmee, FL
7% off
Price is S$2,520
S$2,520
S$360 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 S$2,992
S$2,992
S$427 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
(72 reviews)
6BR Villa with Pool in Windsor at Westside Resort, Near Disney World
Kissimmee, FL
10% off
Price is S$2,604
S$2,604
S$372 per night
includes taxes & fees
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
7% off
Price is S$2,711
S$2,711
S$387 per night
includes taxes & fees
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 S$2,283
S$2,283
S$326 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
(141 reviews)
Waterfront Luxury, 8-bedroom Villa w/ Private Pool - 15 mins from Disney World
Kissimmee, FL
7% off
Price is S$4,649
S$4,649
S$664 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 S$2,264
S$2,264
S$323 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 S$1,850
S$1,850
S$264 per night
includes taxes & fees
Image gallery for Spring Break Dates Still Available!
1010 out of 10 rating
Exceptional
(24 reviews)
Spring Break Dates Still Available!
Kissimmee, FL
7% off
Price is S$3,469
S$3,469
S$496 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
(13 reviews)
Townhouse in Kissimmee Your perfect family getaway Fits up to 15 people! 4ba4be
Kissimmee, FL
10% off
Price is S$1,845
S$1,845
S$264 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
(116 reviews)
Luxury Villa Pool/HotTub/Karaoke 7B Windsor Westside Resort,Disney,Kissimmee
Kissimmee, FL
7% off
Price is S$3,787
S$3,787
S$541 per night
includes taxes & fees
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 S$7,282
S$7,282
S$1,040 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
(36 reviews)
Stunning 5bd Retreat, Pool, BBQ & Game Room, Just 20min From Disney
Kissimmee, FL
7% off
Price is S$2,513
S$2,513
S$359 per night
includes taxes & fees
Image gallery for Magical Theme Rooms, Water Park, Arcade, Sleep 18!
1010 out of 10 rating
Exceptional
(6 reviews)
Magical Theme Rooms, Water Park, Arcade, Sleep 18!
Kissimmee, FL
8% off
Price is S$4,237
S$4,237
S$605 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
8% off
Price is S$3,203
S$3,203
S$458 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
5% off
Price is S$4,048
S$4,048
S$578 per night
includes taxes & fees
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
(6 reviews)
NEW OPENING! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
Kissimmee, FL
7% off
Price is S$2,055
S$2,055
S$294 per night
includes taxes & fees
Image gallery for Pool, BBQ, Game & Movie Room - Unforgettable stay!
8.08.0 out of 10 rating
Very good
(5 reviews)
Pool, BBQ, Game & Movie Room - Unforgettable stay!
Kissimmee, FL
7% off
Price is S$2,658
S$2,658
S$380 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 S$3,252
S$3,252
S$465 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
7% off
Price is S$2,927
S$2,927
S$418 per night
includes taxes & fees
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
5% off
Price is S$1,481
S$1,481
S$212 per night
includes taxes & fees
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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
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)
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
13 reviews(13 reviews)
Beautiful Spacious Home w/Pool & Spa, Resort Community w/amenities, Game Room, Close to Disney!
Sleeps 14 · 7 bedrooms · 5 bathrooms
9.09.0 out of 10
Wonderfulwonderful
27 reviews(27 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