Windsor at Westside holiday rentals
We found 1,044 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor at Westside
Showing deals for:27 Feb - 6 Mar
Image gallery for 9Br/6Ba luxurious Pool House with lake view from 280/nt, Close To Disney
8.28.2 out of 10, Very good, (18 reviews)
Very good
(18 reviews)
9Br/6Ba luxurious Pool House with lake view from 280/nt, Close To Disney
Kissimmee, FL
20% off
Price is AU$6,201
AU$6,201
for 7 nights, 1 home
AU$886 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 AU$3,062
AU$3,062
for 7 nights, 1 home
AU$437 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 AU$3,267
AU$3,267
for 7 nights, 1 home
AU$467 per night
includes taxes & fees
Image gallery for Fully Loaded! Free Pool Heat-2 Game Rooms-Lazy River and Free Resort
1010 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
Fully Loaded! Free Pool Heat-2 Game Rooms-Lazy River and Free Resort
Kissimmee, FL
11% off
Price is AU$7,174
AU$7,174
for 7 nights, 1 villa
AU$1,025 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
24% off
Price is AU$4,911
AU$4,911
for 7 nights, 1 villa
AU$702 per night
includes taxes & fees
Image gallery for 8br/6ba pool villa from $290/NT , Close to Disney
9.69.6 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)
8br/6ba pool villa from $290/NT , Close to Disney
Kissimmee, FL
26% off
Price is AU$4,647
AU$4,647
for 7 nights, 1 home
AU$664 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 AU$5,229
AU$5,229
for 7 nights, 1 home
AU$747 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 AU$5,911
AU$5,911
for 7 nights, 1 home
AU$844 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 AU$4,403
AU$4,403
for 7 nights, 1 home
AU$629 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 AU$4,817
AU$4,817
for 7 nights, 1 home
AU$688 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, FL
7% off
Price is AU$3,028
AU$3,028
for 7 nights, 1 home
AU$433 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 AU$5,503
AU$5,503
for 7 nights, 1 home
AU$786 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 AU$3,433
AU$3,433
for 7 nights, 1 home
AU$490 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, Wonderful, (40 reviews)
Wonderful
(40 reviews)
Stunning 5bd Retreat, Pool, BBQ & Game Room, Just 20min From Disney
Kissimmee, FL
7% off
Price is AU$3,604
AU$3,604
for 7 nights, 1 home
AU$515 per night
includes taxes & fees
Image gallery for Magical Getaway with PVT Pool, Spa, Game Room & Fun Themed Bedrooms Near Disney
8.88.8 out of 10, Excellent, (10 reviews)
Excellent
(10 reviews)
Magical Getaway with PVT Pool, Spa, Game Room & Fun Themed Bedrooms Near Disney
Kissimmee, FL
7% off
Price is AU$3,586
AU$3,586
for 7 nights, 1 home
AU$512 per night
includes taxes & fees
Image gallery for Kissimmee Resort Home w/ Pool, Game Room & Themed Decor Near Parks
8.88.8 out of 10, Excellent, (23 reviews)
Excellent
(23 reviews)
Kissimmee Resort Home w/ Pool, Game Room & Themed Decor Near Parks
Kissimmee, FL
7% off
Price is AU$3,608
AU$3,608
for 7 nights, 1 home
AU$515 per night
includes taxes & fees
Image gallery for Upstay: Renovated 9BR Home w Theater & Games Room
9.69.6 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Upstay: Renovated 9BR Home w Theater & Games Room
Kissimmee, FL
7% off
Price is AU$5,309
AU$5,309
for 7 nights, 1 home
AU$758 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 AU$4,419
AU$4,419
for 7 nights, 1 villa
AU$631 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 AU$4,223
AU$4,223
for 7 nights, 1 home
AU$603 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 AU$5,827
AU$5,827
for 7 nights, 1 home
AU$832 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 AU$3,216
AU$3,216
for 7 nights, 1 home
AU$459 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
7% off
Price is AU$5,500
AU$5,500
for 7 nights, 1 home
AU$786 per night
includes taxes & fees
Image gallery for 9062- Great Home near Disney, Pool & SPA - Windsor at Westside Resort
9.89.8 out of 10, Exceptional, (35 reviews)
Exceptional
(35 reviews)
9062- Great Home near Disney, Pool & SPA - Windsor at Westside Resort
Kissimmee, FL
5% off
Price is AU$4,378
AU$4,378
for 7 nights, 1 home
AU$625 per night
includes taxes & fees
Image gallery for NEW LUXURY LAKE FRONT VILLA. Hot Tub, Pool, Games Room, Windsor at Westside
9.29.2 out of 10, Wonderful, (36 reviews)
Wonderful
(36 reviews)
NEW LUXURY LAKE FRONT VILLA. Hot Tub, Pool, Games Room, Windsor at Westside
Kissimmee, FL
7% off
Price is AU$5,722
AU$5,722
for 7 nights, 1 villa
AU$817 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Windsor at Westside
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)
Dream House Facing South with Lake View Next Disney World - Windsor at Westside
Sleeps 10 · 4 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
16 reviews(16 reviews)
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)
Cozy Family Villa 5BR Pool Spa Near Disney ,8
Sleeps 11 · 5 bedrooms · 4 bathrooms
7.27.2 out of 10
Goodgood
5 reviews(5 reviews)
Epic Fall Getaway, Near Parks, Free Resort Amenities, Room For Multiple Families
Sleeps 12 · 5 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
11 reviews(11 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