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:31 Oct - 7 Nov
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
7% off
Price is AU$5,706
AU$5,706
AU$815 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 AU$4,398
AU$4,398
AU$628 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
27% off
Price is AU$3,810
AU$3,810
AU$544 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 AU$2,546
AU$2,546
AU$364 per night
includes taxes & fees
Image gallery for Stunning 5bd Retreat, Pool, BBQ & Game Room, Just 20min From Disney
9.29.2 out of 10 rating
Wonderful
(39 reviews)
Stunning 5bd Retreat, Pool, BBQ & Game Room, Just 20min From Disney
Kissimmee, FL
7% off
Price is AU$2,659
AU$2,659
AU$380 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 AU$6,277
AU$6,277
AU$897 per night
includes taxes & fees
Image gallery for Windsor Luxury 9Bd Villa South-facing Pool/Spa BBQ Game Room/3min Walk to club
9.29.2 out of 10 rating
Wonderful
(77 reviews)
Windsor Luxury 9Bd Villa South-facing Pool/Spa BBQ Game Room/3min Walk to club
Kissimmee, FL
7% off
Price is AU$4,470
AU$4,470
AU$639 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 AU$6,297
AU$6,297
AU$900 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 AU$2,391
AU$2,391
AU$342 per night
includes taxes & fees
Image gallery for Beautiful 6-bedroom house, themed rooms, game room, wi-fi, minutes from Disney
9.09.0 out of 10 rating
Wonderful
(24 reviews)
Beautiful 6-bedroom house, themed rooms, game room, wi-fi, minutes from Disney
Kissimmee, FL
7% off
Price is AU$5,152
AU$5,152
AU$736 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 AU$2,635
AU$2,635
AU$376 per night
includes taxes & fees
Image gallery for New Opening! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
9.09.0 out of 10 rating
Wonderful
(6 reviews)
New Opening! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
Kissimmee, FL
7% off
Price is AU$2,635
AU$2,635
AU$376 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 AU$4,177
AU$4,177
AU$597 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
5% off
Price is AU$5,810
AU$5,810
AU$830 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
26% off
Price is AU$3,992
AU$3,992
AU$570 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 AU$4,443
AU$4,443
AU$635 per night
includes taxes & fees
Image gallery for Game Room | Private Pool | Gym | 19 Mins to Disney
8.48.4 out of 10 rating
Very good
(14 reviews)
Game Room | Private Pool | Gym | 19 Mins to Disney
Kissimmee, Florida
7% off
Price is AU$4,512
AU$4,512
AU$645 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 AU$3,783
AU$3,783
AU$540 per night
includes taxes & fees
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 AU$3,588
AU$3,588
AU$513 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 rating
Wonderful
(70 reviews)
High cost performance!!! New 9 Br/6 Ba Pool Villa, Close To Disney
Kissimmee, FL
26% off
Price is AU$4,215
AU$4,215
AU$602 per night
includes taxes & fees
Image gallery for Family Paradise Close to Disney w/ Resort Amenities!
8.08.0 out of 10 rating
Very good
(7 reviews)
Family Paradise Close to Disney w/ Resort Amenities!
Kissimmee, FL
6% off
Price is AU$3,010
AU$3,010
AU$430 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 AU$4,252
AU$4,252
AU$607 per night
includes taxes & fees
Image gallery for Villa w/ Heated pool & FREE Waterpark near Disney
8.08.0 out of 10 rating
Very good
(7 reviews)
Villa w/ Heated pool & FREE Waterpark near Disney
Kissimmee, Florida
14% off
Price is AU$3,600
AU$3,600
AU$514 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 AU$3,081
AU$3,081
AU$440 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Windsor at Westside
5BR Home w/ Pool - Windsor at Westside (8890GC)
Sleeps 13 · 5 bedrooms · 4+ bathrooms
7.87.8 out of 10
Goodgood
52 reviews(52 reviews)
Cozy Family Villa 5BR Pool Spa Near Disney ,8
Sleeps 11 · 5 bedrooms · 4 bathrooms
5.05.0 out of 10
2 reviews(2 reviews)
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)
Windsor at Westside Home with Private pool!!
Sleeps 10 · 5 bedrooms · 4+ bathrooms
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)
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)
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