Windsor at Westside holiday lettings
We found 985 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor at Westside
Showing deals for:7 Nov - 14 Nov
Image gallery for 9Br/6Ba luxurious Pool House with lake view from 280/nt, Close To Disney
8.28.2 out of 10 rating
Very good
(18 reviews)
9Br/6Ba luxurious Pool House with lake view from 280/nt, Close To Disney
Kissimmee, FL
25% off
Price is £2,155
£2,155
£308 per night
includes taxes & fees
Image gallery for Cost-effective! 8bd/6ba pool house with lake view, close to Disney
9.09.0 out of 10 rating
Wonderful
(18 reviews)
Cost-effective! 8bd/6ba pool house with lake view, close to Disney
Kissimmee, FL
27% off
Price is £1,814
£1,814
£259 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 £2,043
£2,043
£292 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
(32 reviews)
Spacious Home with Pvt Pool and Resort Amenities. Perfect for Disney Getaways!
Kissimmee, FL
7% off
Price is £1,759
£1,759
£251 per night
includes taxes & fees
Image gallery for 5BR Resort Home Pvt Pool BBQ
9.49.4 out of 10 rating
Exceptional
(24 reviews)
5BR Resort Home Pvt Pool BBQ
Kissimmee, FL
10% off
Price is £1,356
£1,356
£194 per night
includes taxes & fees
Image gallery for 🏝🏝🏝 Luxury Windsor Villa! Newly Furnished and Upgraded, Near Disney
9.69.6 out of 10 rating
Exceptional
(85 reviews)
🏝🏝🏝 Luxury Windsor Villa! Newly Furnished and Upgraded, Near Disney
Kissimmee, FL
7% off
Price is £2,466
£2,466
£352 per night
includes taxes & fees
Image gallery for Magical Themed Retreat w/ Pool Close to Disney
8.88.8 out of 10 rating
Excellent
(23 reviews)
Magical Themed Retreat w/ Pool Close to Disney
Kissimmee, FL
6% off
Price is £1,380
£1,380
£197 per night
includes taxes & fees
Image gallery for 8br/6ba pool villa with lake view, Near Disney
9.09.0 out of 10 rating
Wonderful
(12 reviews)
8br/6ba pool villa with lake view, Near Disney
Kissimmee, FL
26% off
Price is £1,862
£1,862
£266 per night
includes taxes & fees
Image gallery for Magical Theme Rooms, Water Park, Arcade, Sleep 18!
1010 out of 10 rating
Exceptional
(9 reviews)
Magical Theme Rooms, Water Park, Arcade, Sleep 18!
Kissimmee, FL
8% off
Price is £2,566
£2,566
£367 per night
includes taxes & fees
Image gallery for Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/Spa/WiFI
8.48.4 out of 10 rating
Very good
(65 reviews)
Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/Spa/WiFI
Kissimmee, FL
6% off
Price is £1,475
£1,475
£211 per night
includes taxes & fees
Image gallery for Family Fun! ☀️ Private Heated Pool & Spa 4mi to Disney! 🦩
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Family Fun! ☀️ Private Heated Pool & Spa 4mi to Disney! 🦩
Kissimmee, FL
7% off
Price is £3,401
£3,401
£486 per night
includes taxes & fees
Image gallery for Closest House to Resort • Star Wars Adventure + Home Theater!
1010 out of 10 rating
Exceptional
(28 reviews)
Closest House to Resort • Star Wars Adventure + Home Theater!
Kissimmee, FL
14% off
Price is £1,965
£1,965
£281 per night
includes taxes & fees
Image gallery for Cost-effective!!! 9Br/6Ba Pool Villa with lake view,Near Disney
8.68.6 out of 10 rating
Excellent
(13 reviews)
Cost-effective!!! 9Br/6Ba Pool Villa with lake view,Near Disney
Kissimmee, FL
25% off
Price is £2,089
£2,089
£298 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
(37 reviews)
Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
Kissimmee, FL
7% off
Price is £1,382
£1,382
£197 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
7% off
Price is £1,566
£1,566
£224 per night
includes taxes & fees
Image gallery for Amazing Themes | Luxury Villa | FREE Arcade & Theater
9.09.0 out of 10 rating
Wonderful
(8 reviews)
Amazing Themes | Luxury Villa | FREE Arcade & Theater
Kissimmee, FL
7% off
Price is £3,739
£3,739
£534 per night
includes taxes & fees
Image gallery for Closest Units to Clubhouse/Waterpark - Beautiful Townhome 20 Minutes from Disney
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Closest Units to Clubhouse/Waterpark - Beautiful Townhome 20 Minutes from Disney
Kissimmee, FL
8% off
Price is £1,287
£1,287
£184 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
(27 reviews)
5Star Resort/Contctless Checkin/Mins to Parks/WaterPark/Arcade/Bar/Gym/AC/WiFi
Kissimmee, FL
6% off
Price is £2,895
£2,895
£414 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
5% off
Price is £3,507
£3,507
£501 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 £1,331
£1,331
£190 per night
includes taxes & fees
Image gallery for Resort-style Lazy River! 9Br/6Ba lake view Pool House, Close to Disney
8.68.6 out of 10 rating
Excellent
(10 reviews)
Resort-style Lazy River! 9Br/6Ba lake view Pool House, Close to Disney
Kissimmee, FL
23% off
Price is £2,162
£2,162
£309 per night
includes taxes & fees
Image gallery for High cost performance!!! 9Br/6Ba Pool Villa, Close To Disney
8.68.6 out of 10 rating
Excellent
(7 reviews)
High cost performance!!! 9Br/6Ba Pool Villa, Close To Disney
Kissimmee, FL
25% off
Price is £2,122
£2,122
£303 per night
includes taxes & fees
Image gallery for Perfect vacation getaway 8br/6ba home, private pool! close to disney
8.68.6 out of 10 rating
Excellent
(23 reviews)
Perfect vacation getaway 8br/6ba home, private pool! close to disney
Kissimmee, FL
23% off
Price is £1,887
£1,887
£270 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 £1,051
£1,051
£150 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Windsor at Westside
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)
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)
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)
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)
Windsor @ Westside 5 Bed, Private townhouse, Private Pool, Wonderful Amenities
Sleeps 10 · 5 bedrooms · 4+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
94 reviews(94 reviews)
Windsor at Westside Home with Private pool!!
Sleeps 10 · 5 bedrooms · 4+ bathrooms
Top rated rentals - Windsor at Westside
Perfect Holiday Home
1010 out of 10
Exceptionalexceptional
66 reviews(66 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