Windsor at Westside holiday rentals
We found 1,037 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor at Westside
Showing deals for:30 Jan - 6 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 AU$3,866
AU$3,866
for 7 nights, 1 home
AU$552 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, Exceptional, (72 reviews)
Exceptional
(72 reviews)
6BR Villa with Pool in Windsor at Westside Resort, Near Disney World
Kissimmee, FL
23% off
Price is AU$2,558
AU$2,558
for 7 nights, 1 villa
AU$365 per night
includes taxes & fees
Image gallery for High cost performance!!! New 9 Br/6 Ba Pool Villa, Close To Disney
9.09.0 out of 10, Wonderful, (71 reviews)
Wonderful
(71 reviews)
High cost performance!!! New 9 Br/6 Ba Pool Villa, Close To Disney
Kissimmee, FL
24% off
Price is AU$4,684
AU$4,684
for 7 nights, 1 home
AU$669 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$2,849
AU$2,849
for 7 nights, 1 home
AU$407 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 AU$4,254
AU$4,254
for 7 nights, 1 villa
AU$608 per night
includes taxes & fees
Image gallery for Magical Theme Rooms, Water Park, Arcade, Sleep 18!
1010 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
Magical Theme Rooms, Water Park, Arcade, Sleep 18!
Kissimmee, FL
8% off
Price is AU$4,959
AU$4,959
for 7 nights, 1 home
AU$708 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, Exceptional, (79 reviews)
Exceptional
(79 reviews)
Windsor Luxury 9Bd Villa South-facing Pool/Spa BBQ Game Room/3min Walk to club
Kissimmee, FL
7% off
Price is AU$4,396
AU$4,396
for 7 nights, 1 villa
AU$628 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 AU$4,294
AU$4,294
for 7 nights, 1 home
AU$613 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 AU$4,746
AU$4,746
for 7 nights, 1 home
AU$678 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$5,797
AU$5,797
for 7 nights, 1 home
AU$828 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 AU$4,383
AU$4,383
for 7 nights, 1 home
AU$626 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 AU$4,151
AU$4,151
for 7 nights, 1 home
AU$593 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 AU$4,333
AU$4,333
for 7 nights, 1 home
AU$619 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$3,857
AU$3,857
for 7 nights, 1 home
AU$551 per night
includes taxes & fees
Image gallery for 24 HOUR FLASH SALE - 5 STAR DISNEY VACATION HOME
9.49.4 out of 10, Exceptional, (57 reviews)
Exceptional
(57 reviews)
24 HOUR FLASH SALE - 5 STAR DISNEY VACATION HOME
Kissimmee, FL
7% off
Price is AU$3,864
AU$3,864
for 7 nights, 1 home
AU$552 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$5,396
AU$5,396
for 7 nights, 1 home
AU$771 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 AU$3,213
AU$3,213
for 7 nights, 1 home
AU$459 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$2,726
AU$2,726
for 7 nights, 1 home
AU$389 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
5% off
Price is AU$3,437
AU$3,437
for 7 nights, 1 home
AU$491 per night
includes taxes & fees
Image gallery for Sleeps 20! Resort Home Near Disney, Pool+Game Room | Twice-as-Nice by AvantStay
9.69.6 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
Sleeps 20! Resort Home Near Disney, Pool+Game Room | Twice-as-Nice by AvantStay
Kissimmee, FL
6% off
Price is AU$4,587
AU$4,587
for 7 nights, 1 home
AU$655 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$3,400
AU$3,400
for 7 nights, 1 home
AU$486 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$3,031
AU$3,031
for 7 nights, 1 home
AU$433 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 AU$4,339
AU$4,339
for 7 nights, 1 home
AU$620 per night
includes taxes & fees
Image gallery for Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
1010 out of 10, Exceptional, (39 reviews)
Exceptional
(39 reviews)
Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
Kissimmee, FL
7% off
Price is AU$2,842
AU$2,842
for 7 nights, 1 home
AU$406 per night
includes taxes & fees
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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)
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)
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 Townhome Steps From Clubhouse Amenities!
Sleeps 9 · 4 bedrooms · 3+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
7 reviews(7 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