Windsor at Westside holiday lettings
We found 1,008 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor at Westside
Showing deals for:17 Oct - 24 Oct
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 £1,519
£1,519
£217 per night
includes taxes & fees
Image gallery for Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/Spa/WiFI
8.68.6 out of 10 rating
Excellent
(64 reviews)
Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/Spa/WiFI
Kissimmee, FL
6% off
Price is £1,941
£1,941
£277 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
(118 reviews)
Luxury Villa Pool/HotTub/Karaoke 7B Windsor Westside Resort,Disney,Kissimmee
Kissimmee, FL
7% off
Price is £2,187
£2,187
£312 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 £2,533
£2,533
£362 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
7% off
Price is £1,335
£1,335
£191 per night
includes taxes & fees
Image gallery for Closest Units to Clubhouse/Waterpark - Beautiful Townhome 20 Minutes from Disney
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Closest Units to Clubhouse/Waterpark - Beautiful Townhome 20 Minutes from Disney
Kissimmee, FL
8% off
Price is £1,283
£1,283
£183 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 £1,367
£1,367
£195 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
5% off
Price is £1,021
£1,021
£146 per night
includes taxes & fees
Image gallery for NEW OPENING! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
9.29.2 out of 10 rating
Wonderful
(11 reviews)
NEW OPENING! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
Kissimmee, FL
7% off
Price is £1,335
£1,335
£191 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 £1,962
£1,962
£280 per night
includes taxes & fees
Image gallery for NEW LUXURY LAKE FRONT VILLA. Hot Tub, Pool, Games Room, Windsor at Westside
9.29.2 out of 10 rating
Wonderful
(36 reviews)
NEW LUXURY LAKE FRONT VILLA. Hot Tub, Pool, Games Room, Windsor at Westside
Kissimmee, FL
7% off
Price is £2,859
£2,859
£408 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 £1,456
£1,456
£208 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
13% off
Price is £1,324
£1,324
£189 per night
includes taxes & fees
Image gallery for Villa w/ Heated pool & FREE Waterpark near Disney
8.08.0 out of 10 rating
Very good
(6 reviews)
Villa w/ Heated pool & FREE Waterpark near Disney
Kissimmee, Florida
14% off
Price is £1,848
£1,848
£264 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
(16 reviews)
Townhouse in Kissimmee Your perfect family getaway Fits up to 15 people! 4ba4be
Kissimmee, FL
10% off
Price is £1,107
£1,107
£158 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
6% off
Price is £1,347
£1,347
£192 per night
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
13% off
Price is £1,209
£1,209
£173 per night
includes taxes & fees
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Find the best place to stay - Windsor at Westside
Showing deals for: 17 Oct - 20 Oct
5BR Home w/ Pool - Windsor at Westside (8890GC)
Sleeps 13 · 5 bedrooms · 4+ bathrooms
7.87.8 out of 10
Goodgood
52 reviews(52 reviews)
The current price is £645
£645
for 3 nights, 1 home
£215 per night
includes taxes & fees
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)
The current price is £861
£861
for 3 nights, 1 villa
£287 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 £585
£585
for 3 nights, 1 home
£195 per night
includes taxes & fees
[New Opening] 5b4b BBQ&HeatPool. Themed Rooms; Next to Disney
Sleeps 12 · 5 bedrooms · 4+ bathrooms
6.66.6 out of 10
7 reviews(7 reviews)
The current price is £714
£714
for 3 nights, 1 villa
£238 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
16 reviews(16 reviews)
The current price is £652
£652
for 3 nights, 1 home
£217 per night
includes taxes & fees
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
38 reviews(38 reviews)
The current price is £748
£748
for 3 nights, 1 home
£249 per night
includes taxes & fees
Top rated rentals - Windsor at Westside
Top class holiday accommodation in Kissimmee
1010 out of 10
Exceptionalexceptional
35 reviews(35 reviews)
Our stay March/April 2024
1010 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
Excellent Location, Property and Owners
1010 out of 10
Exceptionalexceptional
142 reviews(142 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, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value