Windsor at Westside holiday rentals
We found 1,005 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor at Westside
Showing deals for:21 Nov - 28 Nov
Image gallery for Closest House to Resort • Star Wars Adventure + Home Theater!
1010 out of 10 rating
Exceptional
(29 reviews)
Closest House to Resort • Star Wars Adventure + Home Theater!
Kissimmee, FL
8% off
Price is S$5,453
S$5,453
S$779 nightly
Includes taxes & fees
Image gallery for RENOVATED VILLA@WINDSOR@WESTSIDE !! Private Pool&Spa, ❤Mins2Disney❤A/C game room
1010 out of 10 rating
Exceptional
(28 reviews)
RENOVATED VILLA@WINDSOR@WESTSIDE !! Private Pool&Spa, ❤Mins2Disney❤A/C game room
Kissimmee, FL
12% off
Price is S$5,885
S$5,885
S$841 nightly
Includes taxes & fees
Image gallery for Luxury 5 Beds Villa with Private Pool - Carefully Sanitized - 8843 GC
9.09.0 out of 10 rating
Wonderful
(40 reviews)
Luxury 5 Beds Villa with Private Pool - Carefully Sanitized - 8843 GC
Kissimmee, FL
6% off
Price is S$2,404
S$2,404
S$343 nightly
Includes taxes & fees
Image gallery for Family Fun! ☀️ Private Heated Pool & Spa 4mi to Disney! 🦩
9.69.6 out of 10 rating
Exceptional
(19 reviews)
Family Fun! ☀️ Private Heated Pool & Spa 4mi to Disney! 🦩
Kissimmee, FL
8% off
Price is S$8,877
S$8,877
S$1,268 nightly
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
7% off
Price is S$3,073
S$3,073
S$439 nightly
Includes taxes & fees
Image gallery for Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
1010 out of 10 rating
Exceptional
(38 reviews)
Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
Kissimmee, FL
7% off
Price is S$2,750
S$2,750
S$393 nightly
Includes taxes & fees
Image gallery for Splash pool home near Disney World Orlando
1010 out of 10 rating
Exceptional
(5 reviews)
Splash pool home near Disney World Orlando
Kissimmee, FL
27% off
Price is S$2,871
S$2,871
S$410 nightly
Includes taxes & fees
Image gallery for Dream Townhome at Windsor at Westside
9.49.4 out of 10 rating
Exceptional
(22 reviews)
Dream Townhome at Windsor at Westside
Kissimmee, FL
6% off
Price is S$2,475
S$2,475
S$354 nightly
Includes taxes & fees
Image gallery for Contemporary Design Cozy Vacation Home
9.29.2 out of 10 rating
Wonderful
(79 reviews)
Contemporary Design Cozy Vacation Home
Kissimmee, FL
8% off
Price is S$4,270
S$4,270
S$610 nightly
Includes taxes & fees
Image gallery for Cozy Townhome Steps From Clubhouse Amenities!
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Cozy Townhome Steps From Clubhouse Amenities!
Kissimmee, FL
11% off
Price is S$2,131
S$2,131
S$304 nightly
Includes taxes & fees
Image gallery for Dream Vacation Home, Townhome, Pv Pool Themed Bedroom, BBQ & Club Access
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Dream Vacation Home, Townhome, Pv Pool Themed Bedroom, BBQ & Club Access
Kissimmee, FL
7% off
Price is S$3,134
S$3,134
S$448 nightly
Includes taxes & fees
Image gallery for NEW OPENING! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
8.88.8 out of 10 rating
Excellent
(12 reviews)
NEW OPENING! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
Kissimmee, FL
7% off
Price is S$2,803
S$2,803
S$400 nightly
Includes taxes & fees
Image gallery for Family Fun, Lazy River, Pool, Disney 15 min away
8.88.8 out of 10 rating
Excellent
(6 reviews)
Family Fun, Lazy River, Pool, Disney 15 min away
Kissimmee, FL
7% off
Price is S$3,026
S$3,026
S$432 nightly
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, FL
7% off
Price is S$4,301
S$4,301
S$614 nightly
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
7% off
Price is S$4,259
S$4,259
S$608 nightly
Includes taxes & fees
Image gallery for Family Paradise Near Disney - Private Pool, Game Room, Themed Suites
8.08.0 out of 10 rating
Very good
(5 reviews)
Family Paradise Near Disney - Private Pool, Game Room, Themed Suites
Kissimmee, FL
7% off
Price is S$2,995
S$2,995
S$428 nightly
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, FL
15% off
Price is S$5,920
S$5,920
S$846 nightly
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 S$3,021
S$3,021
S$432 nightly
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 S$2,749
S$2,749
S$393 nightly
Includes taxes & fees
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Find the best place to stay - Windsor at Westside
Cozy Family Villa 5BR Pool Spa Near Disney ,8
Sleeps 11 · 5 bedrooms · 4 bathrooms
6.06.0 out of 10
3 reviews(3 reviews)
5BR Home w/ Pool - Windsor at Westside (8890GC)
Sleeps 13 · 5 bedrooms · 4+ bathrooms
7.87.8 out of 10
Goodgood
53 reviews(53 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
39 reviews(39 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
15 reviews(15 reviews)
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)
4BR Luxury Townhome with Lazy River & Pool Close to Disney
Sleeps 10 · 4 bedrooms · 3 bathrooms
9.09.0 out of 10
Wonderfulwonderful
2 reviews(2 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