Windsor at Westside holiday homes
We found 974 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor at Westside
Showing deals for:14 Nov - 21 Nov
Image gallery for Fully Loaded! Free Pool Heat-2 Game Rooms-Lazy River and Free Resort
1010 out of 10 rating
Exceptional
(12 reviews)
Fully Loaded! Free Pool Heat-2 Game Rooms-Lazy River and Free Resort
Kissimmee, FL
11% off
Price is NZ$5,710
NZ$5,710
NZ$816 per night
includes taxes & fees
Image gallery for Luxury Villa Pool/HotTub/Karaoke 7B Windsor Westside Resort,Disney,Kissimmee
9.69.6 out of 10 rating
Exceptional
(118 reviews)
Luxury Villa Pool/HotTub/Karaoke 7B Windsor Westside Resort,Disney,Kissimmee
Kissimmee, FL
7% off
Price is NZ$4,817
NZ$4,817
NZ$688 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 NZ$3,139
NZ$3,139
NZ$448 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 rating
Wonderful
(16 reviews)
Lazy River!!! 8br/6ba pool villa from $270/NT, Close to Disney
Kissimmee, FL
26% off
Price is NZ$4,518
NZ$4,518
NZ$645 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 rating
Exceptional
(5 reviews)
Dream Vacation Home, Townhome, Pv Pool Themed Bedroom, BBQ & Club Access
Kissimmee, FL
7% off
Price is NZ$3,349
NZ$3,349
NZ$478 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 NZ$5,735
NZ$5,735
NZ$819 per night
includes taxes & fees
Image gallery for RENOVATED VILLA@WINDSOR@WESTSIDE !! Private Pool&Spa, ❤Mins2Disney❤A/C game room
1010 out of 10 rating
Exceptional
(27 reviews)
RENOVATED VILLA@WINDSOR@WESTSIDE !! Private Pool&Spa, ❤Mins2Disney❤A/C game room
Kissimmee, FL
11% off
Price is NZ$5,604
NZ$5,604
NZ$801 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
(12 reviews)
8br/6ba pool villa with lake view, Near Disney
Kissimmee, FL
26% off
Price is NZ$4,074
NZ$4,074
NZ$582 per night
includes taxes & fees
Image gallery for Cozy 5BR Family Resort Home With Private Pool/BBQ/More! – Near Disney!
8.68.6 out of 10 rating
Excellent
(18 reviews)
Cozy 5BR Family Resort Home With Private Pool/BBQ/More! – Near Disney!
Kissimmee, FL
21% off
Price is NZ$2,730
NZ$2,730
NZ$390 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
8% off
Price is NZ$2,817
NZ$2,817
NZ$402 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
(19 reviews)
Family Fun! ☀️ Private Heated Pool & Spa 4mi to Disney! 🦩
Kissimmee, FL
7% off
Price is NZ$7,286
NZ$7,286
NZ$1,041 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 NZ$8,355
NZ$8,355
NZ$1,194 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 NZ$2,958
NZ$2,958
NZ$423 per night
includes taxes & fees
Image gallery for Family Paradise Near Disney - Private Pool, Game Room, Themed Suites
8.08.0 out of 10 rating
Very good
(5 reviews)
Family Paradise Near Disney - Private Pool, Game Room, Themed Suites
Kissimmee, FL
7% off
Price is NZ$3,202
NZ$3,202
NZ$457 per night
includes taxes & fees
Image gallery for 24 HOUR FLASH SALE - 5 STAR DISNEY VACATION HOME
9.49.4 out of 10 rating
Exceptional
(57 reviews)
24 HOUR FLASH SALE - 5 STAR DISNEY VACATION HOME
Kissimmee, FL
7% off
Price is NZ$4,343
NZ$4,343
NZ$620 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 NZ$3,008
NZ$3,008
NZ$430 per night
includes taxes & fees
Image gallery for 6BR Villa with Pool in Windsor at Westside Resort, Near Disney World
9.69.6 out of 10 rating
Exceptional
(72 reviews)
6BR Villa with Pool in Windsor at Westside Resort, Near Disney World
Kissimmee, FL
11% off
Price is NZ$3,544
NZ$3,544
NZ$506 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 NZ$4,022
NZ$4,022
NZ$575 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
25% off
Price is NZ$4,617
NZ$4,617
NZ$660 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
25% off
Price is NZ$4,306
NZ$4,306
NZ$615 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 NZ$4,518
NZ$4,518
NZ$645 per night
includes taxes & fees
Image gallery for Spacious 5-bedroom Town home Pvt Pool, BBQ & Free Water Park Access Near Disney
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Spacious 5-bedroom Town home Pvt Pool, BBQ & Free Water Park Access Near Disney
Kissimmee, FL
7% off
Price is NZ$3,245
NZ$3,245
NZ$464 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 NZ$4,794
NZ$4,794
NZ$685 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, FL
7% off
Price is NZ$4,526
NZ$4,526
NZ$647 per night
includes taxes & fees
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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
53 reviews(53 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)
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)
4BR Luxury Townhome with Lazy River & Pool Close to Disney
Sleeps 10 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Windsor @ Westside 5 Bed, Private townhouse, Private Pool, Wonderful Amenities
Sleeps 10 · 5 bedrooms · 4+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
95 reviews(95 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)
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