Windsor at Westside holiday homes
We found 1,036 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, (44 reviews)
Exceptional
(44 reviews)
9027 - Great Family Home Near Disney, Pool.
Kissimmee, FL
5% off
Price is NZ$5,113
NZ$5,113
for 7 nights, 1 home
NZ$730 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$5,406
NZ$5,406
for 7 nights, 1 villa
NZ$772 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$3,377
NZ$3,377
for 7 nights, 1 home
NZ$482 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$6,011
NZ$6,011
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$5,892
NZ$5,892
for 7 nights, 1 home
NZ$842 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$5,314
NZ$5,314
for 7 nights, 1 home
NZ$759 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$6,781
NZ$6,781
for 7 nights, 1 home
NZ$969 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$5,422
NZ$5,422
for 7 nights, 1 home
NZ$775 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$3,699
NZ$3,699
for 7 nights, 1 villa
NZ$528 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$4,600
NZ$4,600
for 7 nights, 1 home
NZ$657 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$5,529
NZ$5,529
for 7 nights, 1 home
NZ$790 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$3,322
NZ$3,322
for 7 nights, 1 home
NZ$475 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$6,313
NZ$6,313
for 7 nights, 1 home
NZ$902 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$4,129
NZ$4,129
for 7 nights, 1 home
NZ$590 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$3,838
NZ$3,838
for 7 nights, 1 home
NZ$548 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$3,637
NZ$3,637
for 7 nights, 1 home
NZ$520 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$5,196
NZ$5,196
for 7 nights, 1 villa
NZ$742 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$5,897
NZ$5,897
for 7 nights, 1 home
NZ$842 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$4,394
NZ$4,394
for 7 nights, 1 home
NZ$628 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$6,337
NZ$6,337
for 7 nights, 1 home
NZ$905 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$3,346
NZ$3,346
for 7 nights, 1 home
NZ$478 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$8,676
NZ$8,676
for 7 nights, 1 home
NZ$1,239 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$4,886
NZ$4,886
for 7 nights, 1 home
NZ$698 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$5,404
NZ$5,404
for 7 nights, 1 home
NZ$772 per night
includes taxes & fees
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Find the best place to stay - Windsor at Westside
Showing deals for: 1 Feb - 4 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$1,946
NZ$1,946
for 3 nights, 1 villa
NZ$649 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$1,428
NZ$1,428
for 3 nights, 1 home
NZ$476 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$1,539
NZ$1,539
for 3 nights, 1 home
NZ$513 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$1,398
NZ$1,398
for 3 nights, 1 home
NZ$466 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$1,530
NZ$1,530
for 3 nights, 1 home
NZ$510 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