Windsor at Westside holiday rentals
We found 1,033 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 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 S$2,161
S$2,161
for 7 nights, 1 villa
S$309 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 S$3,656
S$3,656
for 7 nights, 1 villa
S$522 per night
includes taxes & fees
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 S$3,352
S$3,352
for 7 nights, 1 home
S$479 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
23% off
Price is S$4,026
S$4,026
for 7 nights, 1 home
S$575 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 S$4,263
S$4,263
for 7 nights, 1 home
S$609 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 S$3,778
S$3,778
for 7 nights, 1 villa
S$540 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$4,982
S$4,982
for 7 nights, 1 home
S$712 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 S$3,767
S$3,767
for 7 nights, 1 home
S$538 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$4,073
S$4,073
for 7 nights, 1 home
S$582 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 S$3,566
S$3,566
for 7 nights, 1 home
S$509 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 S$3,690
S$3,690
for 7 nights, 1 home
S$527 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$3,300
S$3,300
for 7 nights, 1 home
S$471 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 S$3,320
S$3,320
for 7 nights, 1 home
S$474 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 S$2,337
S$2,337
for 7 nights, 1 home
S$334 per night
includes taxes & fees
Image gallery for Sleeps 20! Resort Home Near Disney, Pool+Game Room | Twice-as-Nice by AvantStay
9.89.8 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
Sleeps 20! Resort Home Near Disney, Pool+Game Room | Twice-as-Nice by AvantStay
Kissimmee, FL
6% off
Price is S$3,944
S$3,944
for 7 nights, 1 home
S$563 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 S$3,723
S$3,723
for 7 nights, 1 home
S$532 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 S$3,728
S$3,728
for 7 nights, 1 home
S$533 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
23% off
Price is S$3,959
S$3,959
for 7 nights, 1 home
S$566 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$4,638
S$4,638
for 7 nights, 1 home
S$663 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 S$2,955
S$2,955
for 7 nights, 1 home
S$422 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 S$2,401
S$2,401
for 7 nights, 1 home
S$343 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 S$2,902
S$2,902
for 7 nights, 1 home
S$415 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$2,970
S$2,970
for 7 nights, 1 villa
S$424 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$2,747
S$2,747
for 7 nights, 1 home
S$392 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
100 reviews(100 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