Windsor at Westside holiday homes
We found 981 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor at Westside
Showing deals for:3 Oct - 10 Oct
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 NZ$2,205
NZ$2,205
NZ$315 per night
includes taxes & fees
Image gallery for Townhouse in Kissimmee Your perfect family getaway Fits up to 15 people! 4ba4be
8.08.0 out of 10 rating
Very good
(15 reviews)
Townhouse in Kissimmee Your perfect family getaway Fits up to 15 people! 4ba4be
Kissimmee, FL
11% off
Price is NZ$2,351
NZ$2,351
NZ$336 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
(34 reviews)
Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
Kissimmee, FL
13% off
Price is NZ$2,396
NZ$2,396
NZ$342 per night
includes taxes & fees
Image gallery for 9035 Amazing 5BD Family Home!
8.68.6 out of 10 rating
Excellent
(14 reviews)
9035 Amazing 5BD Family Home!
Kissimmee, FL
7% off
Price is NZ$2,494
NZ$2,494
NZ$356 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
(11 reviews)
Spacious 5-bedroom Town home Pvt Pool, BBQ & Free Water Park Access Near Disney
Kissimmee, FL
14% off
Price is NZ$2,608
NZ$2,608
NZ$373 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
13% off
Price is NZ$2,615
NZ$2,615
NZ$374 per night
includes taxes & fees
Image gallery for Closest Units to Clubhouse/Waterpark - Beautiful Townhome 20 Minutes from Disney
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Closest Units to Clubhouse/Waterpark - Beautiful Townhome 20 Minutes from Disney
Kissimmee, FL
9% off
Price is NZ$2,726
NZ$2,726
NZ$389 per night
includes taxes & fees
Image gallery for New Opening! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
9.69.6 out of 10 rating
Exceptional
(5 reviews)
New Opening! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
Kissimmee, FL
7% off
Price is NZ$2,821
NZ$2,821
NZ$403 per night
includes taxes & fees
Image gallery for NEW OPENING! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
9.69.6 out of 10 rating
Exceptional
(8 reviews)
NEW OPENING! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
Kissimmee, FL
7% off
Price is NZ$2,821
NZ$2,821
NZ$403 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$3,005
NZ$3,005
NZ$429 per night
includes taxes & fees
Image gallery for Resort-Style Stay | Private Pool, Lazy River & Gym
8.88.8 out of 10 rating
Excellent
(6 reviews)
Resort-Style Stay | Private Pool, Lazy River & Gym
Kissimmee, Florida
7% off
Price is NZ$3,115
NZ$3,115
NZ$445 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
10% off
Price is NZ$3,252
NZ$3,252
NZ$465 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
(6 reviews)
Villa w/ Heated pool & FREE Waterpark near Disney
Kissimmee, Florida
14% off
Price is NZ$3,724
NZ$3,724
NZ$532 per night
includes taxes & fees
Image gallery for Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/Spa/WiFI
8.68.6 out of 10 rating
Excellent
(64 reviews)
Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/Spa/WiFI
Kissimmee, FL
7% off
Price is NZ$4,037
NZ$4,037
NZ$577 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
7% off
Price is NZ$4,092
NZ$4,092
NZ$585 per night
includes taxes & fees
Image gallery for Windsor Fairytale is a 7 Bed Condo w/ pull-out sofa minutes from Disney!
1010 out of 10 rating
Exceptional
(9 reviews)
Windsor Fairytale is a 7 Bed Condo w/ pull-out sofa minutes from Disney!
Kissimmee, FL
8% off
Price is NZ$4,138
NZ$4,138
NZ$591 per night
includes taxes & fees
Image gallery for Spring Break Dates Still Available!
1010 out of 10 rating
Exceptional
(26 reviews)
Spring Break Dates Still Available!
Kissimmee, FL
7% off
Price is NZ$4,147
NZ$4,147
NZ$592 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$4,152
NZ$4,152
NZ$593 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$4,379
NZ$4,379
NZ$626 per night
includes taxes & fees
Image gallery for Magical Theme Rooms, Water Park, Arcade, Sleep 18!
1010 out of 10 rating
Exceptional
(7 reviews)
Magical Theme Rooms, Water Park, Arcade, Sleep 18!
Kissimmee, FL
8% off
Price is NZ$4,462
NZ$4,462
NZ$637 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$4,682
NZ$4,682
NZ$669 per night
includes taxes & fees
Image gallery for Sleeps 20! Resort Home Near Disney, Pool+Game Room | Twice-as-Nice by AvantStay
1010 out of 10 rating
Exceptional
(7 reviews)
Sleeps 20! Resort Home Near Disney, Pool+Game Room | Twice-as-Nice by AvantStay
Kissimmee, Florida
6% off
Price is NZ$4,749
NZ$4,749
NZ$678 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 rating
Exceptional
(75 reviews)
Windsor Luxury 9Bd Villa South-facing Pool/Spa BBQ Game Room/3min Walk to club
Kissimmee, FL
7% off
Price is NZ$4,783
NZ$4,783
NZ$683 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 NZ$5,271
NZ$5,271
NZ$753 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Windsor at Westside
Showing deals for: 2 Oct - 5 Oct
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)
The current price is NZ$1,349
NZ$1,349
for 3 nights, 1 home
NZ$450 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
92 reviews(92 reviews)
The current price is NZ$1,430
NZ$1,430
for 3 nights, 1 home
NZ$477 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 NZ$1,241
NZ$1,241
for 3 nights, 1 home
NZ$414 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 NZ$1,531
NZ$1,531
for 3 nights, 1 villa
NZ$510 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
15 reviews(15 reviews)
The current price is NZ$1,395
NZ$1,395
for 3 nights, 1 home
NZ$465 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 NZ$1,857
NZ$1,857
for 3 nights, 1 villa
NZ$619 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