Windsor at Westside holiday homes
We found 989 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor at Westside
Showing deals for:25 Jul - 1 Aug
Image gallery for Prestige 1: Stunning Windsor at Westside, South Facing Pool/Spa, Game Rm
9.89.8 out of 10 rating
Exceptional
(30 reviews)
Prestige 1: Stunning Windsor at Westside, South Facing Pool/Spa, Game Rm
Kissimmee, FL
5% off
Price is NZ$6,074
NZ$6,074
NZ$868 per night
includes taxes & fees
Image gallery for High Quality South Facing Lake View Vacation Home 8BR/6BA
9.89.8 out of 10 rating
Exceptional
(74 reviews)
High Quality South Facing Lake View Vacation Home 8BR/6BA
Kissimmee, FL
6% off
Price is NZ$6,907
NZ$6,907
NZ$987 per night
includes taxes & fees
Image gallery for Family Fun! ☀️ Private Heated Pool & Spa 4mi to Disney! 🦩
1010 out of 10 rating
Exceptional
(14 reviews)
Family Fun! ☀️ Private Heated Pool & Spa 4mi to Disney! 🦩
Kissimmee, FL
8% off
Price is NZ$10,281
NZ$10,281
NZ$1,469 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$5,536
NZ$5,536
NZ$791 per night
includes taxes & fees
Image gallery for Prestige 1:Modern home away from home, South Facing Pool/Spa, Game Rm
9.89.8 out of 10 rating
Exceptional
(69 reviews)
Prestige 1:Modern home away from home, South Facing Pool/Spa, Game Rm
Kissimmee, FL
5% off
Price is NZ$5,723
NZ$5,723
NZ$818 per night
includes taxes & fees
Image gallery for Spring Break Dates Still Available!
1010 out of 10 rating
Exceptional
(23 reviews)
Spring Break Dates Still Available!
Kissimmee, FL
7% off
Price is NZ$5,996
NZ$5,996
NZ$857 per night
includes taxes & fees
Image gallery for Ultimate 5BR Windsor Westside Pool Villa, Close to Disney,No Rear Neighbor
8.88.8 out of 10 rating
Excellent
(23 reviews)
Ultimate 5BR Windsor Westside Pool Villa, Close to Disney,No Rear Neighbor
Kissimmee, FL
7% off
Price is NZ$5,550
NZ$5,550
NZ$793 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 NZ$4,616
NZ$4,616
NZ$659 per night
includes taxes & fees
Image gallery for Private Pool, Resort-Style Perks, Near Disney Fun
8.88.8 out of 10 rating
Excellent
(6 reviews)
Private Pool, Resort-Style Perks, Near Disney Fun
Kissimmee, Florida
7% off
Price is NZ$3,398
NZ$3,398
NZ$485 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
(115 reviews)
Luxury Villa Pool/HotTub/Karaoke 7B Windsor Westside Resort,Disney,Kissimmee
Kissimmee, FL
7% off
Price is NZ$5,030
NZ$5,030
NZ$719 per night
includes taxes & fees
Image gallery for Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
9.89.8 out of 10 rating
Exceptional
(28 reviews)
Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
Kissimmee, FL
6% off
Price is NZ$3,593
NZ$3,593
NZ$513 per night
includes taxes & fees
Image gallery for 5 stars Resort--8 BedRm/6 Bath Lake Front Private Pool- Just 6 miles Disney!
8.08.0 out of 10 rating
Very good
(13 reviews)
5 stars Resort--8 BedRm/6 Bath Lake Front Private Pool- Just 6 miles Disney!
Kissimmee, FL
8% off
Price is NZ$10,353
NZ$10,353
NZ$1,479 per night
includes taxes & fees
Image gallery for Pool, BBQ, Game & Movie Room - Unforgettable stay!
8.08.0 out of 10 rating
Very good
(5 reviews)
Pool, BBQ, Game & Movie Room - Unforgettable stay!
Kissimmee, FL
6% off
Price is NZ$4,145
NZ$4,145
NZ$592 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
(31 reviews)
Spacious Home with Pvt Pool and Resort Amenities. Perfect for Disney Getaways!
Kissimmee, FL
6% off
Price is NZ$4,801
NZ$4,801
NZ$686 per night
includes taxes & fees
Image gallery for Spacious 5-bedroom Town home Pvt Pool, BBQ & Free Water Park Access Near Disney
1010 out of 10 rating
Exceptional
(6 reviews)
Spacious 5-bedroom Town home Pvt Pool, BBQ & Free Water Park Access Near Disney
Kissimmee, FL
6% off
Price is NZ$3,953
NZ$3,953
NZ$565 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
(8 reviews)
Windsor Fairytale is a 7 Bed Condo w/ pull-out sofa minutes from Disney!
Kissimmee, FL
8% off
Price is NZ$4,477
NZ$4,477
NZ$640 per night
includes taxes & fees
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Find the best place to stay - Windsor at Westside
Dream House Facing South with Lake View Next Disney World - Windsor at Westside
Sleeps 10 · 4 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/Spa/WiFI
Sleeps 18 · 7 bedrooms · 5+ bathrooms
8.68.6 out of 10
Excellentexcellent
61 reviews(61 reviews)
Cozy Family Villa 5BR Pool Spa Near Disney ,8
Sleeps 11 · 5 bedrooms · 4 bathrooms
4.04.0 out of 10
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
87 reviews(87 reviews)
Sleeps 20! Resort Home Near Disney, Pool+Game Room | Twice-as-Nice by AvantStay
Sleeps 20 · 8 bedrooms · 6 bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
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
11 reviews(11 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