Windsor at Westside holiday rentals
We found 987 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor at Westside
Showing deals for:7 Nov - 14 Nov
Image gallery for Cost-effective! 8bd/6ba pool house with lake view, close to Disney
9.09.0 out of 10 rating
Wonderful
(18 reviews)
Cost-effective! 8bd/6ba pool house with lake view, close to Disney
Kissimmee, FL
27% off
Price is S$3,040
S$3,040
S$434 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 rating
Very good
(18 reviews)
9Br/6Ba luxurious Pool House with lake view from 280/nt, Close To Disney
Kissimmee, FL
26% off
Price is S$3,596
S$3,596
S$514 per night
includes taxes & fees
Image gallery for 5BD/4.5BA home, 9 mi. from Disney, Free Access to Lazy River and Waterpark!
1010 out of 10 rating
Exceptional
(6 reviews)
5BD/4.5BA home, 9 mi. from Disney, Free Access to Lazy River and Waterpark!
Kissimmee, FL
8% off
Price is S$3,422
S$3,422
S$489 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 rating
Wonderful
(32 reviews)
Spacious Home with Pvt Pool and Resort Amenities. Perfect for Disney Getaways!
Kissimmee, FL
7% off
Price is S$2,948
S$2,948
S$421 per night
includes taxes & fees
Image gallery for 🏝🏝🏝 Luxury Windsor Villa! Newly Furnished and Upgraded, Near Disney
9.69.6 out of 10 rating
Exceptional
(85 reviews)
🏝🏝🏝 Luxury Windsor Villa! Newly Furnished and Upgraded, Near Disney
Kissimmee, FL
7% off
Price is S$4,121
S$4,121
S$589 per night
includes taxes & fees
Image gallery for Magical Themed Retreat w/ Pool Close to Disney
8.88.8 out of 10 rating
Excellent
(23 reviews)
Magical Themed Retreat w/ Pool Close to Disney
Kissimmee, FL
7% off
Price is S$2,278
S$2,278
S$325 per night
includes taxes & fees
Image gallery for Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/Spa/WiFI
8.48.4 out of 10 rating
Very good
(65 reviews)
Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/Spa/WiFI
Kissimmee, FL
6% off
Price is S$2,463
S$2,463
S$352 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 rating
Excellent
(13 reviews)
Cost-effective!!! 9Br/6Ba Pool Villa with lake view,Near Disney
Kissimmee, FL
26% off
Price is S$3,490
S$3,490
S$499 per night
includes taxes & fees
Image gallery for 8br/6ba pool villa with lake view, Near Disney
9.09.0 out of 10 rating
Wonderful
(11 reviews)
8br/6ba pool villa with lake view, Near Disney
Kissimmee, FL
26% off
Price is S$3,122
S$3,122
S$446 per night
includes taxes & fees
Image gallery for Magical Theme Rooms, Water Park, Arcade, Sleep 18!
1010 out of 10 rating
Exceptional
(9 reviews)
Magical Theme Rooms, Water Park, Arcade, Sleep 18!
Kissimmee, FL
8% off
Price is S$4,254
S$4,254
S$608 per night
includes taxes & fees
Image gallery for Closest House to Resort • Star Wars Adventure + Home Theater!
1010 out of 10 rating
Exceptional
(28 reviews)
Closest House to Resort • Star Wars Adventure + Home Theater!
Kissimmee, FL
14% off
Price is S$3,352
S$3,352
S$479 per night
includes taxes & fees
Image gallery for Family Fun! ☀️ Private Heated Pool & Spa 4mi to Disney! 🦩
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Family Fun! ☀️ Private Heated Pool & Spa 4mi to Disney! 🦩
Kissimmee, FL
8% off
Price is S$5,675
S$5,675
S$811 per night
includes taxes & fees
Image gallery for Resort like: Pool, BBQ, Xbox & Club Access with Lazy River – 15 Min to Disney!
9.69.6 out of 10 rating
Exceptional
(20 reviews)
Resort like: Pool, BBQ, Xbox & Club Access with Lazy River – 15 Min to Disney!
Kissimmee, FL
7% off
Price is S$2,627
S$2,627
S$375 per night
includes taxes & fees
Image gallery for Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
1010 out of 10 rating
Exceptional
(37 reviews)
Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
Kissimmee, FL
7% off
Price is S$2,296
S$2,296
S$328 per night
includes taxes & fees
Image gallery for Amazing Themes | Luxury Villa | FREE Arcade & Theater
9.09.0 out of 10 rating
Wonderful
(8 reviews)
Amazing Themes | Luxury Villa | FREE Arcade & Theater
Kissimmee, FL
7% off
Price is S$6,257
S$6,257
S$894 per night
includes taxes & fees
Image gallery for Closest Units to Clubhouse/Waterpark - Beautiful Townhome 20 Minutes from Disney
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Closest Units to Clubhouse/Waterpark - Beautiful Townhome 20 Minutes from Disney
Kissimmee, FL
9% off
Price is S$2,130
S$2,130
S$304 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 rating
Wonderful
(36 reviews)
NEW LUXURY LAKE FRONT VILLA. Hot Tub, Pool, Games Room, Windsor at Westside
Kissimmee, FL
5% off
Price is S$5,808
S$5,808
S$830 per night
includes taxes & fees
Image gallery for 5Star Resort/Contctless Checkin/Mins to Parks/WaterPark/Arcade/Bar/Gym/AC/WiFi
8.68.6 out of 10 rating
Excellent
(27 reviews)
5Star Resort/Contctless Checkin/Mins to Parks/WaterPark/Arcade/Bar/Gym/AC/WiFi
Kissimmee, FL
6% off
Price is S$4,763
S$4,763
S$680 per night
includes taxes & fees
Image gallery for NEW OPENING! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
9.29.2 out of 10 rating
Wonderful
(11 reviews)
NEW OPENING! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
Kissimmee, FL
7% off
Price is S$2,204
S$2,204
S$315 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 rating
Excellent
(10 reviews)
Resort-style Lazy River! 9Br/6Ba lake view Pool House, Close to Disney
Kissimmee, FL
23% off
Price is S$3,625
S$3,625
S$518 per night
includes taxes & fees
Image gallery for High cost performance!!! 9Br/6Ba Pool Villa, Close To Disney
8.68.6 out of 10 rating
Excellent
(7 reviews)
High cost performance!!! 9Br/6Ba Pool Villa, Close To Disney
Kissimmee, FL
26% off
Price is S$3,516
S$3,516
S$502 per night
includes taxes & fees
Image gallery for Luxury 5 Beds Villa with Private Pool - Carefully Sanitized - 8843 GC
9.29.2 out of 10 rating
Wonderful
(39 reviews)
Luxury 5 Beds Villa with Private Pool - Carefully Sanitized - 8843 GC
Kissimmee, FL
5% off
Price is S$1,749
S$1,749
S$250 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 rating
Excellent
(23 reviews)
Perfect vacation getaway 8br/6ba home, private pool! close to disney
Kissimmee, FL
23% off
Price is S$3,162
S$3,162
S$452 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 rating
Very good
(5 reviews)
8br/6ba pool villa, Close to Disney,Resort-style heated Pool and Lazy River
Kissimmee, FL
25% off
Price is S$3,033
S$3,033
S$433 per night
includes taxes & fees
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Find the best place to stay - Windsor at Westside
Showing deals for: 1 Nov - 4 Nov
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
38 reviews(38 reviews)
The current price is S$1,234
S$1,234
for 3 nights, 1 home
S$411 per night
includes taxes & fees
Dream House Facing South with Lake View Next Disney World - Windsor at Westside
Sleeps 10 · 4 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
The current price is S$943
S$943
for 3 nights, 1 home
S$314 per night
includes taxes & fees
Windsor @ Westside 5 Bed, Private townhouse, Private Pool, Wonderful Amenities
Sleeps 10 · 5 bedrooms · 4+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
94 reviews(94 reviews)
The current price is S$1,117
S$1,117
for 3 nights, 1 home
S$372 per night
includes taxes & fees
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)
The current price is S$1,307
S$1,307
for 3 nights, 1 villa
S$436 per night
includes taxes & fees
Townhouse in Kissimmee Your perfect family getaway Fits up to 15 people! 4ba4be
Sleeps 14 · 5 bedrooms · 4+ bathrooms
8.08.0 out of 10
Very goodvery good
17 reviews(17 reviews)
The current price is S$1,090
S$1,090
for 3 nights, 1 home
S$363 per night
includes taxes & fees
[New Opening] 5b4b BBQ&HeatPool. Themed Rooms; Next to Disney
Sleeps 12 · 5 bedrooms · 4+ bathrooms
6.66.6 out of 10
7 reviews(7 reviews)
The current price is S$988
S$988
for 3 nights, 1 villa
S$329 per night
includes taxes & fees
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