Windsor at Westside holiday homes
We found 1,030 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 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 NZ$5,187
NZ$5,187
for 7 nights, 1 home
NZ$741 per night
includes taxes & fees
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
23% off
Price is NZ$5,485
NZ$5,485
for 7 nights, 1 villa
NZ$784 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 NZ$3,446
NZ$3,446
for 7 nights, 1 home
NZ$492 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 NZ$6,015
NZ$6,015
for 7 nights, 1 home
NZ$859 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
23% off
Price is NZ$5,978
NZ$5,978
for 7 nights, 1 home
NZ$854 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 NZ$6,880
NZ$6,880
for 7 nights, 1 home
NZ$983 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
23% off
Price is NZ$5,392
NZ$5,392
for 7 nights, 1 home
NZ$770 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
23% off
Price is NZ$5,501
NZ$5,501
for 7 nights, 1 home
NZ$786 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 NZ$3,774
NZ$3,774
for 7 nights, 1 villa
NZ$539 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 NZ$4,667
NZ$4,667
for 7 nights, 1 home
NZ$667 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
23% off
Price is NZ$5,610
NZ$5,610
for 7 nights, 1 home
NZ$801 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 NZ$3,384
NZ$3,384
for 7 nights, 1 home
NZ$483 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 NZ$6,405
NZ$6,405
for 7 nights, 1 home
NZ$915 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 NZ$4,189
NZ$4,189
for 7 nights, 1 home
NZ$598 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 NZ$3,679
NZ$3,679
for 7 nights, 1 home
NZ$526 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 NZ$3,894
NZ$3,894
for 7 nights, 1 home
NZ$556 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 NZ$5,200
NZ$5,200
for 7 nights, 1 villa
NZ$743 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 NZ$5,983
NZ$5,983
for 7 nights, 1 home
NZ$855 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 NZ$4,447
NZ$4,447
for 7 nights, 1 home
NZ$635 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 NZ$3,395
NZ$3,395
for 7 nights, 1 home
NZ$485 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 NZ$6,558
NZ$6,558
for 7 nights, 1 home
NZ$937 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 NZ$8,795
NZ$8,795
for 7 nights, 1 home
NZ$1,256 per night
includes taxes & fees
Image gallery for Family Paradise Close to Disney w/ Resort Amenities!
8.08.0 out of 10, Very good, (7 reviews)
Very good
(7 reviews)
Family Paradise Close to Disney w/ Resort Amenities!
Kissimmee, FL
6% off
Price is NZ$4,952
NZ$4,952
for 7 nights, 1 home
NZ$707 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
23% off
Price is NZ$5,483
NZ$5,483
for 7 nights, 1 home
NZ$783 per night
includes taxes & fees
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Find the best place to stay - Windsor at Westside
Showing deals for: 3 Feb - 6 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 NZ$1,930
NZ$1,930
for 3 nights, 1 villa
NZ$643 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 NZ$1,441
NZ$1,441
for 3 nights, 1 home
NZ$480 per night
includes taxes & fees
Beautiful 9-bedroom Windsor house near Disney
Sleeps 20 · 9 bedrooms · 6 bathrooms
8.08.0 out of 10
Very goodvery good
The current price is NZ$2,258
NZ$2,258
for 3 nights, 1 home
NZ$753 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 NZ$1,543
NZ$1,543
for 3 nights, 1 home
NZ$514 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 NZ$1,410
NZ$1,410
for 3 nights, 1 home
NZ$470 per night
includes taxes & fees
Cozy Townhome Steps From Clubhouse Amenities!
Sleeps 9 · 4 bedrooms · 3+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
The current price is NZ$1,576
NZ$1,576
for 3 nights, 1 home
NZ$525 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