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:23 Jan - 30 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$2,155
S$2,155
for 7 nights, 1 villa
S$308 per night
includes taxes & fees
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
23% off
Price is S$3,611
S$3,611
for 7 nights, 1 home
S$516 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$4,306
S$4,306
for 7 nights, 1 villa
S$615 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$3,603
S$3,603
for 7 nights, 1 home
S$515 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$3,033
S$3,033
for 7 nights, 1 villa
S$433 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$3,768
S$3,768
for 7 nights, 1 villa
S$538 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$4,196
S$4,196
for 7 nights, 1 home
S$599 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$4,969
S$4,969
for 7 nights, 1 home
S$710 per night
includes taxes & fees
Image gallery for 🎮 Mario’s Magic Mansion – Pool, Games, 4mi to Disney 🎢
9.49.4 out of 10, Exceptional, (21 reviews)
Exceptional
(21 reviews)
🎮 Mario’s Magic Mansion – Pool, Games, 4mi to Disney 🎢
Kissimmee, FL
7% off
Price is S$4,682
S$4,682
for 7 nights, 1 home
S$669 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$3,532
S$3,532
for 7 nights, 1 home
S$505 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$3,110
S$3,110
for 7 nights, 1 home
S$444 per night
includes taxes & fees
Image gallery for Resort-style Lazy River! 9Br/6Ba lake view Pool House, Close to Disney
8.68.6 out of 10, Excellent, (10 reviews)
Excellent
(10 reviews)
Resort-style Lazy River! 9Br/6Ba lake view Pool House, Close to Disney
Kissimmee, FL
23% off
Price is S$3,769
S$3,769
for 7 nights, 1 home
S$538 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$3,312
S$3,312
for 7 nights, 1 home
S$473 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$2,877
S$2,877
for 7 nights, 1 home
S$411 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$3,110
S$3,110
for 7 nights, 1 home
S$444 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$4,626
S$4,626
for 7 nights, 1 home
S$661 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$3,611
S$3,611
for 7 nights, 1 home
S$516 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$2,214
S$2,214
for 7 nights, 1 home
S$316 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$3,891
S$3,891
for 7 nights, 1 home
S$556 per night
includes taxes & fees
Image gallery for Cost-effective!!! 9Br/6Ba Pool Villa with lake view,Near Disney
9.29.2 out of 10, Wonderful, (5 reviews)
Wonderful
(5 reviews)
Cost-effective!!! 9Br/6Ba Pool Villa with lake view,Near Disney
Kissimmee, FL
23% off
Price is S$3,611
S$3,611
for 7 nights, 1 home
S$516 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$2,736
S$2,736
for 7 nights, 1 home
S$391 per night
includes taxes & fees
Image gallery for Upstay: Renovated 9BR Home w Theater & Games Room
9.89.8 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Upstay: Renovated 9BR Home w Theater & Games Room
Kissimmee, FL
7% off
Price is S$3,459
S$3,459
for 7 nights, 1 home
S$494 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$2,697
S$2,697
for 7 nights, 1 home
S$385 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$2,402
S$2,402
for 7 nights, 1 home
S$343 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
16 reviews(16 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)
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)
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