Windsor at Westside holiday homes
We found 988 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 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 NZ$7,578
NZ$7,578
NZ$1,083 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$2,993
NZ$2,993
NZ$428 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$5,586
NZ$5,586
NZ$798 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 NZ$4,099
NZ$4,099
NZ$586 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 NZ$2,797
NZ$2,797
NZ$400 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 NZ$4,401
NZ$4,401
NZ$629 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 NZ$7,407
NZ$7,407
NZ$1,058 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$8,161
NZ$8,161
NZ$1,166 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$3,017
NZ$3,017
NZ$431 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$2,894
NZ$2,894
NZ$413 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$3,992
NZ$3,992
NZ$570 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 NZ$2,894
NZ$2,894
NZ$413 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 NZ$4,723
NZ$4,723
NZ$675 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 NZ$4,617
NZ$4,617
NZ$660 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$6,221
NZ$6,221
NZ$889 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$3,269
NZ$3,269
NZ$467 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 NZ$4,760
NZ$4,760
NZ$680 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 NZ$3,983
NZ$3,983
NZ$569 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 NZ$4,493
NZ$4,493
NZ$642 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 NZ$4,153
NZ$4,153
NZ$593 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 NZ$3,784
NZ$3,784
NZ$541 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 NZ$4,385
NZ$4,385
NZ$626 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 NZ$3,872
NZ$3,872
NZ$553 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 NZ$3,235
NZ$3,235
NZ$462 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
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)
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)
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)
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
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