Windsor at Westside holiday rentals
We found 1,017 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor at Westside
Showing deals for:6 Feb - 13 Feb
Image gallery for 8br/6ba pool villa with lake view, Near Disney
9.09.0 out of 10, Wonderful, (12 reviews)
Wonderful
(12 reviews)
8br/6ba pool villa with lake view, Near Disney
Kissimmee, FL
24% off
Price is S$3,978
S$3,978
for 7 nights, 1 villa
S$568 per night
includes taxes & fees
Image gallery for Unforgettable Disney Stay, 5BR w/ Xbox One, BBQ, Pool & Resort Clubhouse
8.48.4 out of 10, Very good, (5 reviews)
Very good
(5 reviews)
Unforgettable Disney Stay, 5BR w/ Xbox One, BBQ, Pool & Resort Clubhouse
Kissimmee, FL
7% off
Price is S$2,492
S$2,492
for 7 nights, 1 home
S$356 per night
includes taxes & fees
Image gallery for 9027 - Great Family Home Near Disney, Pool.
9.69.6 out of 10, Exceptional, (45 reviews)
Exceptional
(45 reviews)
9027 - Great Family Home Near Disney, Pool.
Kissimmee, FL
5% off
Price is S$2,695
S$2,695
for 7 nights, 1 home
S$385 per night
includes taxes & fees
Image gallery for New 9Br/6Ba Pool Villa, Close To Disney
8.88.8 out of 10, Excellent, (6 reviews)
Excellent
(6 reviews)
New 9Br/6Ba Pool Villa, Close To Disney
Kissimmee, FL
24% off
Price is S$4,336
S$4,336
for 7 nights, 1 home
S$619 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, Exceptional, (46 reviews)
Exceptional
(46 reviews)
Sun, Fun & Weekly Savings! Family-Pet Retreat w/ Pool + 5★ Clubhouse!
Kissimmee, FL
7% off
Price is S$4,991
S$4,991
for 7 nights, 1 home
S$713 per night
includes taxes & fees
Image gallery for Closest House to Resort • Star Wars Adventure + Home Theater!
1010 out of 10, Exceptional, (30 reviews)
Exceptional
(30 reviews)
Closest House to Resort • Star Wars Adventure + Home Theater!
Kissimmee, FL
7% off
Price is S$4,002
S$4,002
for 7 nights, 1 home
S$572 per night
includes taxes & fees
Image gallery for 8br/6ba pool villa, Close to Disney,Resort-style heated Pool and Lazy River
8.48.4 out of 10, Very good, (5 reviews)
Very good
(5 reviews)
8br/6ba pool villa, Close to Disney,Resort-style heated Pool and Lazy River
Kissimmee, FL
24% off
Price is S$3,911
S$3,911
for 7 nights, 1 home
S$559 per night
includes taxes & fees
Image gallery for Lazy River!!! 8br/6ba pool villa from $270/NT, Close to Disney
9.29.2 out of 10, Wonderful, (17 reviews)
Wonderful
(17 reviews)
Lazy River!!! 8br/6ba pool villa from $270/NT, Close to Disney
Kissimmee, FL
24% off
Price is S$3,990
S$3,990
for 7 nights, 1 home
S$570 per night
includes taxes & fees
Image gallery for Family Vacation Villa Near Disney with Themed Bedrooms, Game Room & Pool
8.88.8 out of 10, Excellent, (23 reviews)
Excellent
(23 reviews)
Family Vacation Villa Near Disney with Themed Bedrooms, Game Room & Pool
Kissimmee, FL
7% off
Price is S$2,821
S$2,821
for 7 nights, 1 villa
S$403 per night
includes taxes & fees
Image gallery for Relax & Play in This 6BR Home with Pool, BBQ & Ping Pong - Near Disney
9.29.2 out of 10, Wonderful, (5 reviews)
Wonderful
(5 reviews)
Relax & Play in This 6BR Home with Pool, BBQ & Ping Pong - Near Disney
Kissimmee, FL
7% off
Price is S$3,415
S$3,415
for 7 nights, 1 home
S$488 per night
includes taxes & fees
Image gallery for Family Fun, Lazy River, Pool, Disney 15 min away
8.88.8 out of 10, Excellent, (6 reviews)
Excellent
(6 reviews)
Family Fun, Lazy River, Pool, Disney 15 min away
Kissimmee, Florida
7% off
Price is S$2,505
S$2,505
for 7 nights, 1 home
S$358 per night
includes taxes & fees
Image gallery for Perfect vacation getaway 8br/6ba home, private pool! close to disney
8.68.6 out of 10, Excellent, (23 reviews)
Excellent
(23 reviews)
Perfect vacation getaway 8br/6ba home, private pool! close to disney
Kissimmee, FL
24% off
Price is S$4,069
S$4,069
for 7 nights, 1 home
S$581 per night
includes taxes & fees
Image gallery for Dream Townhome at Windsor at Westside
9.49.4 out of 10, Exceptional, (22 reviews)
Exceptional
(22 reviews)
Dream Townhome at Windsor at Westside
Kissimmee, FL
7% off
Price is S$3,039
S$3,039
for 7 nights, 1 home
S$434 per night
includes taxes & fees
Image gallery for 9 Bedroom Luxury Pool Home Ideal for Family Vacation Bubble - Stay Safe
9.49.4 out of 10, Exceptional, (62 reviews)
Exceptional
(62 reviews)
9 Bedroom Luxury Pool Home Ideal for Family Vacation Bubble - Stay Safe
Kissimmee, FL
6% off
Price is S$4,646
S$4,646
for 7 nights, 1 home
S$664 per night
includes taxes & fees
Image gallery for Villa w/ Heated pool & FREE Waterpark near Disney
8.08.0 out of 10, Very good, (7 reviews)
Very good
(7 reviews)
Villa w/ Heated pool & FREE Waterpark near Disney
Kissimmee, FL
14% off
Price is S$3,507
S$3,507
for 7 nights, 1 villa
S$501 per night
includes taxes & fees
Image gallery for Upstay: Renovated 9BR Home w Theater & Games Room
9.69.6 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Upstay: Renovated 9BR Home w Theater & Games Room
Kissimmee, FL
7% off
Price is S$4,104
S$4,104
for 7 nights, 1 home
S$586 per night
includes taxes & fees
Image gallery for Family Paradise Near Disney - Private Pool, Game Room, Themed Suites
8.08.0 out of 10, Very good, (5 reviews)
Very good
(5 reviews)
Family Paradise Near Disney - Private Pool, Game Room, Themed Suites
Kissimmee, FL
7% off
Price is S$2,647
S$2,647
for 7 nights, 1 home
S$378 per night
includes taxes & fees
Image gallery for Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
1010 out of 10, Exceptional, (40 reviews)
Exceptional
(40 reviews)
Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
Kissimmee, FL
7% off
Price is S$2,449
S$2,449
for 7 nights, 1 home
S$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, Wonderful, (32 reviews)
Wonderful
(32 reviews)
Spacious Home with Pvt Pool and Resort Amenities. Perfect for Disney Getaways!
Kissimmee, FL
7% off
Price is S$3,392
S$3,392
for 7 nights, 1 home
S$485 per night
includes taxes & fees
Image gallery for Cost-effective! 8bd/6ba pool house with lake view, close to Disney
9.29.2 out of 10, Wonderful, (19 reviews)
Wonderful
(19 reviews)
Cost-effective! 8bd/6ba pool house with lake view, close to Disney
Kissimmee, FL
24% off
Price is S$3,977
S$3,977
for 7 nights, 1 home
S$568 per night
includes taxes & fees
Image gallery for Cost-effective!!! 9Br/6Ba Pool Villa with lake view,Near Disney
8.68.6 out of 10, Excellent, (14 reviews)
Excellent
(14 reviews)
Cost-effective!!! 9Br/6Ba Pool Villa with lake view,Near Disney
Kissimmee, FL
24% off
Price is S$4,808
S$4,808
for 7 nights, 1 home
S$687 per night
includes taxes & fees
Image gallery for Comfortable Vacation Home - Great Resort | Pool/Spa | Sleeps 20 | WW101
9.09.0 out of 10, Wonderful, (18 reviews)
Wonderful
(18 reviews)
Comfortable Vacation Home - Great Resort | Pool/Spa | Sleeps 20 | WW101
Kissimmee, FL
7% off
Price is S$6,356
S$6,356
for 7 nights, 1 home
S$908 per night
includes taxes & fees
Image gallery for 9001- Great Family Home near Disney, private pool - Windsor at Westside Resort
9.89.8 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
9001- Great Family Home near Disney, private pool - Windsor at Westside Resort
Kissimmee, FL
5% off
Price is S$2,880
S$2,880
for 7 nights, 1 home
S$411 per night
includes taxes & fees
Image gallery for Dream Vacation Home, Townhome, Pv Pool Themed Bedroom, BBQ & Club Access
9.69.6 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)
Dream Vacation Home, Townhome, Pv Pool Themed Bedroom, BBQ & Club Access
Kissimmee, FL
7% off
Price is S$2,861
S$2,861
for 7 nights, 1 home
S$409 per night
includes taxes & fees
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Find the best place to stay - Windsor at Westside
Showing deals for: 6 Feb - 9 Feb
6BR Villa with Pool in Windsor at Westside Resort, Near Disney World
Sleeps 15 · 6 bedrooms · 4+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
72 reviews(72 reviews)
The current price is S$1,508
S$1,508
for 3 nights, 1 villa
S$503 per night
includes taxes & fees
Windsor @ Westside 5 Bed, Private townhouse, Private Pool, Wonderful Amenities
Sleeps 10 · 5 bedrooms · 4+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
101 reviews(101 reviews)
The current price is S$1,053
S$1,053
for 3 nights, 1 home
S$351 per night
includes taxes & fees
Lovely 5BR/4BA w/ Private Heated Pool & BBQ Grill
Sleeps 12 · 5 bedrooms · 4+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
The current price is S$1,482
S$1,482
for 3 nights, 1 home
S$494 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
22 reviews(22 reviews)
The current price is S$1,052
S$1,052
for 3 nights, 1 home
S$351 per night
includes taxes & fees
Private pool~Lazy River~Near Disney~Resort~Pool Table
Sleeps 18 · 8 bedrooms · 6+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
The current price is S$2,142
S$2,142
for 3 nights, 1 home
S$714 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