Windsor at Westside holiday rentals
We found 993 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor at Westside
Showing deals for:22 Aug - 29 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 S$3,017
S$3,017
S$431 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$2,706
S$2,706
S$387 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 S$3,777
S$3,777
S$540 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$4,178
S$4,178
S$597 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
6% off
Price is S$3,386
S$3,386
S$484 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
6% off
Price is S$7,625
S$7,625
S$1,089 per night
includes taxes & fees
Image gallery for Private Pool | Game Room | Resort Perks Near Parks
8.48.4 out of 10 rating
Very good
(14 reviews)
Private Pool | Game Room | Resort Perks Near Parks
Kissimmee, Florida
7% off
Price is S$2,625
S$2,625
S$375 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
(71 reviews)
6BR Villa with Pool in Windsor at Westside Resort, Near Disney World
Kissimmee, FL
10% off
Price is S$2,566
S$2,566
S$367 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 S$3,272
S$3,272
S$467 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$4,679
S$4,679
S$668 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$1,857
S$1,857
S$265 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$2,008
S$2,008
S$287 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$3,224
S$3,224
S$461 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$2,202
S$2,202
S$315 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 S$3,586
S$3,586
S$512 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 S$4,960
S$4,960
S$709 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
6% off
Price is S$2,322
S$2,322
S$332 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
(30 reviews)
Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
Kissimmee, FL
6% off
Price is S$2,105
S$2,105
S$301 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 S$2,008
S$2,008
S$287 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$3,273
S$3,273
S$468 per night
includes taxes & fees
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
6% off
Price is S$3,944
S$3,944
S$563 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 S$3,969
S$3,969
S$567 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
6% off
Price is S$2,455
S$2,455
S$351 per night
includes taxes & fees
Image gallery for NEW OPENING! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
9.29.2 out of 10 rating
Wonderful
(5 reviews)
NEW OPENING! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
Kissimmee, FL
6% off
Price is S$2,249
S$2,249
S$321 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Windsor at Westside
Showing deals for: 18 Aug - 21 Aug
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)
The current price is S$979
S$979
for 3 nights, 1 home
S$326 per night
includes taxes & fees
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)
The current price is S$1,130
S$1,130
for 3 nights, 1 home
S$377 per night
includes taxes & fees
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)
The current price is S$2,225
S$2,225
for 3 nights, 1 home
S$742 per night
includes taxes & fees
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)
The current price is S$1,086
S$1,086
for 3 nights, 1 home
S$362 per night
includes taxes & fees
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)
The current price is S$1,786
S$1,786
for 3 nights, 1 villa
S$595 per night
includes taxes & fees
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)
The current price is S$1,501
S$1,501
for 3 nights, 1 home
S$500 per night
includes taxes & fees
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