Windsor at Westside holiday rentals
We found 984 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor at Westside
Showing deals for:12 Sept - 19 Sept
Image gallery for Sun, Fun & Weekly Savings! Family-Pet Retreat w/ Pool + 5★ Clubhouse!
9.89.8 out of 10 rating
Exceptional
(46 reviews)
Sun, Fun & Weekly Savings! Family-Pet Retreat w/ Pool + 5★ Clubhouse!
Kissimmee, FL
7% off
Price is AU$5,969
AU$5,969
AU$853 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 AU$4,460
AU$4,460
AU$637 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 AU$4,254
AU$4,254
AU$608 per night
includes taxes & fees
Image gallery for Spring Break Dates Still Available!
1010 out of 10 rating
Exceptional
(24 reviews)
Spring Break Dates Still Available!
Kissimmee, FL
7% off
Price is AU$3,654
AU$3,654
AU$522 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 AU$4,080
AU$4,080
AU$583 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 AU$3,030
AU$3,030
AU$433 per night
includes taxes & fees
Image gallery for Waterfront Luxury, 8-bedroom Villa w/ Private Pool - 15 mins from Disney World
9.69.6 out of 10 rating
Exceptional
(141 reviews)
Waterfront Luxury, 8-bedroom Villa w/ Private Pool - 15 mins from Disney World
Kissimmee, FL
7% off
Price is AU$5,525
AU$5,525
AU$789 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 AU$2,226
AU$2,226
AU$318 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
(32 reviews)
Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
Kissimmee, FL
13% off
Price is AU$2,213
AU$2,213
AU$316 per night
includes taxes & fees
Image gallery for Luxury Family Resort Vacation Home
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Luxury Family Resort Vacation Home
Kissimmee, FL
5% off
Price is AU$2,670
AU$2,670
AU$381 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
(117 reviews)
Luxury Villa Pool/HotTub/Karaoke 7B Windsor Westside Resort,Disney,Kissimmee
Kissimmee, FL
7% off
Price is AU$4,366
AU$4,366
AU$624 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 AU$4,329
AU$4,329
AU$618 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
14% off
Price is AU$2,838
AU$2,838
AU$405 per night
includes taxes & fees
Image gallery for Fun Paradise in Kissimmee
1010 out of 10 rating
Exceptional
(7 reviews)
Fun Paradise in Kissimmee
Kissimmee, FL
8% off
Price is AU$3,807
AU$3,807
AU$544 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
(6 reviews)
Sleeps 20! Resort Home Near Disney, Pool+Game Room | Twice-as-Nice by AvantStay
Kissimmee, Florida
6% off
Price is AU$4,469
AU$4,469
AU$638 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
(7 reviews)
NEW OPENING! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
Kissimmee, FL
8% off
Price is AU$2,273
AU$2,273
AU$325 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
(13 reviews)
Townhouse in Kissimmee Your perfect family getaway Fits up to 15 people! 4ba4be
Kissimmee, FL
10% off
Price is AU$2,201
AU$2,201
AU$314 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 AU$2,903
AU$2,903
AU$415 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 AU$3,867
AU$3,867
AU$552 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
8% off
Price is AU$2,273
AU$2,273
AU$325 per night
includes taxes & fees
Image gallery for Comfortable Vacation Home - Great Resort | Pool/Spa | Sleeps 20 | WW101
9.09.0 out of 10 rating
Wonderful
(18 reviews)
Comfortable Vacation Home - Great Resort | Pool/Spa | Sleeps 20 | WW101
Kissimmee, FL
6% off
Price is AU$4,421
AU$4,421
AU$632 per night
includes taxes & fees
Image gallery for Villa w/ Heated pool & FREE Waterpark near Disney
8.88.8 out of 10 rating
Excellent
(5 reviews)
Villa w/ Heated pool & FREE Waterpark near Disney
Kissimmee, Florida
14% off
Price is AU$3,615
AU$3,615
AU$516 per night
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
14% off
Price is AU$2,654
AU$2,654
AU$379 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 AU$2,200
AU$2,200
AU$314 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
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Chalet
Find the best place to stay - Windsor at Westside
Showing deals for: 12 Sept - 15 Sept
Windsor @ Westside 5 Bed, Private townhouse, Private Pool, Wonderful Amenities
Sleeps 10 · 5 bedrooms · 4+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
90 reviews(90 reviews)
The current price is AU$1,333
AU$1,333
for 3 nights, 1 home
AU$444 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 AU$1,157
AU$1,157
for 3 nights, 1 home
AU$386 per night
includes taxes & fees
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
64 reviews(64 reviews)
The current price is AU$2,106
AU$2,106
for 3 nights, 1 villa
AU$702 per night
includes taxes & fees
Family-Friendly Townhouse w/ Private Pool & Patio Kitchen across from Clubhouse
Sleeps 9 · 4 bedrooms · 3+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
40 reviews(40 reviews)
The current price is AU$1,266
AU$1,266
for 3 nights, 1 home
AU$422 per night
includes taxes & fees
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
6 reviews(6 reviews)
The current price is AU$2,754
AU$2,754
for 3 nights, 1 home
AU$918 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
13 reviews(13 reviews)
The current price is AU$1,282
AU$1,282
for 3 nights, 1 home
AU$427 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