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:16 Jan - 23 Jan
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$2,148
S$2,148
for 7 nights, 1 villa
S$307 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 S$4,618
S$4,618
for 7 nights, 1 villa
S$660 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$3,592
S$3,592
for 7 nights, 1 home
S$513 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$3,068
S$3,068
for 7 nights, 1 villa
S$438 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$3,757
S$3,757
for 7 nights, 1 villa
S$537 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$4,423
S$4,423
for 7 nights, 1 home
S$632 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 S$2,402
S$2,402
for 7 nights, 1 home
S$343 per night
includes taxes & fees
Image gallery for 🎮 Mario’s Magic Mansion – Pool, Games, 4mi to Disney 🎢
9.49.4 out of 10, Exceptional, (20 reviews)
Exceptional
(20 reviews)
🎮 Mario’s Magic Mansion – Pool, Games, 4mi to Disney 🎢
Kissimmee, FL
8% off
Price is S$5,346
S$5,346
for 7 nights, 1 home
S$764 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$4,954
S$4,954
for 7 nights, 1 home
S$708 per night
includes taxes & fees
Image gallery for Closest House to Resort • Star Wars Adventure + Home Theater!
1010 out of 10, Exceptional, (29 reviews)
Exceptional
(29 reviews)
Closest House to Resort • Star Wars Adventure + Home Theater!
Kissimmee, FL
7% off
Price is S$3,178
S$3,178
for 7 nights, 1 home
S$454 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$3,522
S$3,522
for 7 nights, 1 home
S$503 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$3,102
S$3,102
for 7 nights, 1 home
S$443 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$3,332
S$3,332
for 7 nights, 1 home
S$476 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$3,302
S$3,302
for 7 nights, 1 home
S$472 per night
includes taxes & fees
Image gallery for Thematic, New Townhouse, Private Pool, Clubhouse
9.29.2 out of 10, Wonderful, (5 reviews)
Wonderful
(5 reviews)
Thematic, New Townhouse, Private Pool, Clubhouse
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 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$2,869
S$2,869
for 7 nights, 1 home
S$410 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$3,102
S$3,102
for 7 nights, 1 home
S$443 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$4,612
S$4,612
for 7 nights, 1 home
S$659 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$3,600
S$3,600
for 7 nights, 1 home
S$514 per night
includes taxes & fees
Image gallery for Escape in Style: Game Room, Pvt Pool, gated community & Resort amenities Await
9.69.6 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)
Escape in Style: Game Room, Pvt Pool, gated community & Resort amenities Await
Kissimmee, FL
7% off
Price is S$2,685
S$2,685
for 7 nights, 1 villa
S$384 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$2,649
S$2,649
for 7 nights, 1 home
S$378 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$2,718
S$2,718
for 7 nights, 1 home
S$388 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$2,416
S$2,416
for 7 nights, 1 home
S$345 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$3,416
S$3,416
for 7 nights, 1 villa
S$488 per night
includes taxes & fees
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Find the best place to stay - Windsor at Westside
Dream House Facing South with Lake View Next Disney World - Windsor at Westside
Sleeps 10 · 4 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
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)
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)
Luxury 5BR Family Mansion with Private Pool & BBQ
Sleeps 10 · 5 bedrooms · 5+ bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Modern Spacious Villa with No Rear Neighbors! Game Room, BBQ Grill, Kid Themed Bedrooms, Free Wi-Fi!
Sleeps 14 · 5 bedrooms · 5 bathrooms
8.88.8 out of 10
Excellentexcellent
39 reviews(39 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