Windsor at Westside holiday homes
We found 1,000 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor at Westside
Showing deals for:1 Aug - 8 Aug
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$6,911
NZ$6,911
NZ$987 per night
includes taxes & fees
Image gallery for Family Fun! ☀️ Private Heated Pool & Spa 4mi to Disney! 🦩
9.89.8 out of 10 rating
Exceptional
(15 reviews)
Family Fun! ☀️ Private Heated Pool & Spa 4mi to Disney! 🦩
Kissimmee, FL
8% off
Price is NZ$8,594
NZ$8,594
NZ$1,228 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$5,726
NZ$5,726
NZ$818 per night
includes taxes & fees
Image gallery for Luxury Family Resort Vacation Home
1010 out of 10 rating
Exceptional
(8 reviews)
Luxury Family Resort Vacation Home
Kissimmee, FL
5% off
Price is NZ$2,979
NZ$2,979
NZ$426 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$4,853
NZ$4,853
NZ$693 per night
includes taxes & fees
Image gallery for Prestige 2: Stunning Windsor at Westside, South Facing Pool/Spa, Game Rm
1010 out of 10 rating
Exceptional
(53 reviews)
Prestige 2: Stunning Windsor at Westside, South Facing Pool/Spa, Game Rm
Kissimmee, FL
5% off
Price is NZ$6,077
NZ$6,077
NZ$868 per night
includes taxes & fees
Image gallery for 15 min from Disney - Only steps away from Huge Pool, Clubhouse, Waterpark
9.69.6 out of 10 rating
Exceptional
(5 reviews)
15 min from Disney - Only steps away from Huge Pool, Clubhouse, Waterpark
Kissimmee, FL
8% off
Price is NZ$2,601
NZ$2,601
NZ$372 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$4,225
NZ$4,225
NZ$604 per night
includes taxes & fees
Image gallery for Magical Theme Rooms, Water Park, Arcade, Sleep 18!
1010 out of 10 rating
Exceptional
(6 reviews)
Magical Theme Rooms, Water Park, Arcade, Sleep 18!
Kissimmee, FL
7% off
Price is NZ$5,643
NZ$5,643
NZ$806 per night
includes taxes & fees
Image gallery for Private Pool,Lazy River & Tiki Bar Fun Near Disney
8.88.8 out of 10 rating
Excellent
(6 reviews)
Private Pool,Lazy River & Tiki Bar Fun Near Disney
Kissimmee, Florida
7% off
Price is NZ$3,215
NZ$3,215
NZ$459 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$5,064
NZ$5,064
NZ$723 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
(11 reviews)
Townhouse in Kissimmee Your perfect family getaway Fits up to 15 people! 4ba4be
Kissimmee, FL
11% off
Price is NZ$2,405
NZ$2,405
NZ$344 per night
includes taxes & fees
Image gallery for Resort Mansion w Pool, Hot Tub, Theatre, Games
8.48.4 out of 10 rating
Very good
(10 reviews)
Resort Mansion w Pool, Hot Tub, Theatre, Games
Kissimmee, Florida
8% off
Price is NZ$6,817
NZ$6,817
NZ$974 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
(26 reviews)
5Star Resort/Contctless Checkin/Mins to Parks/WaterPark/Arcade/Bar/Gym/AC/WiFi
Kissimmee, FL
8% off
Price is NZ$6,417
NZ$6,417
NZ$917 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
(34 reviews)
Stunning 5bd Retreat, Pool, BBQ & Game Room, Just 20min From Disney
Kissimmee, FL
6% off
Price is NZ$3,929
NZ$3,929
NZ$561 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
(29 reviews)
Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
Kissimmee, FL
6% off
Price is NZ$3,510
NZ$3,510
NZ$501 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$4,584
NZ$4,584
NZ$655 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$4,062
NZ$4,062
NZ$580 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
(7 reviews)
Spacious 5-bedroom Town home Pvt Pool, BBQ & Free Water Park Access Near Disney
Kissimmee, FL
6% off
Price is NZ$3,851
NZ$3,851
NZ$550 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
7% off
Price is NZ$4,149
NZ$4,149
NZ$593 per night
includes taxes & fees
Find spaces that suit your style
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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
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
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