Windsor at Westside holiday homes
We found 994 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor at Westside
Showing deals for:8 Aug - 15 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$6,894
NZ$6,894
NZ$985 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
(72 reviews)
Windsor Luxury 9Bd Villa South-facing Pool/Spa BBQ Game Room/3min Walk to club
Kissimmee, FL
7% off
Price is NZ$5,562
NZ$5,562
NZ$795 per night
includes taxes & fees
Image gallery for Luxury Villa!! 8Br/6Ba Resort-Villa-Pool-Near Disney, 10% weekly discount!!
9.89.8 out of 10 rating
Exceptional
(48 reviews)
Luxury Villa!! 8Br/6Ba Resort-Villa-Pool-Near Disney, 10% weekly discount!!
Kissimmee, FL
7% off
Price is NZ$5,341
NZ$5,341
NZ$763 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$5,712
NZ$5,712
NZ$816 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
(16 reviews)
Family Fun! ☀️ Private Heated Pool & Spa 4mi to Disney! 🦩
Kissimmee, FL
8% off
Price is NZ$7,083
NZ$7,083
NZ$1,012 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$5,120
NZ$5,120
NZ$731 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$6,062
NZ$6,062
NZ$866 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$4,859
NZ$4,859
NZ$694 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$5,052
NZ$5,052
NZ$722 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$3,619
NZ$3,619
NZ$517 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$2,595
NZ$2,595
NZ$371 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$3,062
NZ$3,062
NZ$437 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$3,321
NZ$3,321
NZ$474 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$3,981
NZ$3,981
NZ$569 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$4,208
NZ$4,208
NZ$601 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$2,399
NZ$2,399
NZ$343 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$6,401
NZ$6,401
NZ$914 per night
includes taxes & fees
Image gallery for Resort like: Pool, BBQ, Xbox & Club Access with Lazy River – 15 Min to Disney!
9.69.6 out of 10 rating
Exceptional
(20 reviews)
Resort like: Pool, BBQ, Xbox & Club Access with Lazy River – 15 Min to Disney!
Kissimmee, FL
6% off
Price is NZ$3,504
NZ$3,504
NZ$501 per night
includes taxes & fees
Image gallery for Escape in Style: Game Room, Pvt Pool, gated community & Resort amenities Await
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Escape in Style: Game Room, Pvt Pool, gated community & Resort amenities Await
Kissimmee, FL
6% off
Price is NZ$3,692
NZ$3,692
NZ$527 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$3,787
NZ$3,787
NZ$541 per night
includes taxes & fees
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
6% off
Price is NZ$3,114
NZ$3,114
NZ$445 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$3,651
NZ$3,651
NZ$522 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$3,990
NZ$3,990
NZ$570 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Windsor at Westside
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)
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
4 reviews(4 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
11 reviews(11 reviews)
Windsor @ Westside 5 Bed, Private townhouse, Private Pool, Wonderful Amenities
Sleeps 10 · 5 bedrooms · 4+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
88 reviews(88 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