
Windsor at Westside vacation rentals
We found 974 vacation rentals — enter your dates for availability
Vacation rentals with weekly discounts - Windsor at Westside
Showing deals for:Nov 14 - Nov 21
Image gallery for 5BD/4.5BA home, 9 mi. from Disney, Free Access to Lazy River and Waterpark!

1010 out of 10 rating
Exceptional
(7 reviews)
5BD/4.5BA home, 9 mi. from Disney, Free Access to Lazy River and Waterpark!
Kissimmee, FL
10% off
Price is CA $369
CA $369
CA $3,572 total
CA $3,572 total
includes taxes & fees
Image gallery for Lazy River!!! 8br/6ba pool villa from $270/NT, Close to Disney

9.29.2 out of 10 rating
Wonderful
(16 reviews)
Lazy River!!! 8br/6ba pool villa from $270/NT, Close to Disney
Kissimmee, FL
33% off
Price is CA $369
CA $369
CA $3,694 total
CA $3,694 total
includes taxes & fees
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
33% off
Price is CA $374
CA $374
CA $3,774 total
CA $3,774 total
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
35% off
Price is CA $322
CA $322
CA $3,288 total
CA $3,288 total
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
14% off
Price is CA $297
CA $297
CA $2,898 total
CA $2,898 total
includes taxes & fees
Image gallery for Windsor Discovery | Kids Bedrooms | Town Home

1010 out of 10 rating
Exceptional
(6 reviews)
Windsor Discovery | Kids Bedrooms | Town Home
Kissimmee, FL
5% off
Price is CA $167
CA $167
CA $2,044 total
CA $2,044 total
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
15% off
Price is CA $228
CA $228
CA $2,429 total
CA $2,429 total
includes taxes & fees
Image gallery for Fully Loaded! Free Pool Heat-2 Game Rooms-Lazy River and Free Resort

1010 out of 10 rating
Exceptional
(12 reviews)
Fully Loaded! Free Pool Heat-2 Game Rooms-Lazy River and Free Resort
Kissimmee, FL
15% off
Price is CA $458
CA $458
CA $4,668 total
CA $4,668 total
includes taxes & fees
Image gallery for Family Friendly Luxury Themed Villa: Pool, Scavenger Hunt, & Arcade!

1010 out of 10 rating
Exceptional
(5 reviews)
Family Friendly Luxury Themed Villa: Pool, Scavenger Hunt, & Arcade!
Kissimmee, FL
5% off
Price is CA $390
CA $390
CA $3,892 total
CA $3,892 total
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
10% off
Price is CA $443
CA $443
CA $4,457 total
CA $4,457 total
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
10% off
Price is CA $392
CA $392
CA $3,939 total
CA $3,939 total
includes taxes & fees
Image gallery for Cozy 5BR Family Resort Home With Private Pool/BBQ/More! – Near Disney!

8.68.6 out of 10 rating
Excellent
(18 reviews)
Cozy 5BR Family Resort Home With Private Pool/BBQ/More! – Near Disney!
Kissimmee, FL
28% off
Price is CA $205
CA $205
CA $2,230 total
CA $2,230 total
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
15% off
Price is CA $467
CA $467
CA $4,580 total
CA $4,580 total
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
10% off
Price is CA $243
CA $243
CA $2,565 total
CA $2,565 total
includes taxes & fees
Image gallery for 5 stars Resort--8 BedRm/6 Bath Lake Front Private Pool- Just 6 miles Disney!

8.08.0 out of 10 rating
Very good
(13 reviews)
5 stars Resort--8 BedRm/6 Bath Lake Front Private Pool- Just 6 miles Disney!
Kissimmee, FL
5% off
Price is CA $950
CA $950
CA $8,729 total
CA $8,729 total
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
34% off
Price is CA $327
CA $327
CA $3,330 total
CA $3,330 total
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
11% off
Price is CA $460
CA $460
CA $4,688 total
CA $4,688 total
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
10% off
Price is CA $619
CA $619
CA $5,956 total
CA $5,956 total
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
33% off
Price is CA $369
CA $369
CA $3,728 total
CA $3,728 total
includes taxes & fees
Image gallery for Stunning 5 bed/5 bath pool home, games room, beautiful resort, Disney 8 miles!

9.89.8 out of 10 rating
Exceptional
(22 reviews)
Stunning 5 bed/5 bath pool home, games room, beautiful resort, Disney 8 miles!
Kissimmee, FL
5% off
Price is CA $268
CA $268
CA $2,664 total
CA $2,664 total
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
10% off
Price is CA $235
CA $235
CA $2,416 total
CA $2,416 total
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
10% off
Price is CA $222
CA $222
CA $2,663 total
CA $2,663 total
includes taxes & fees
Image gallery for Windsor's Avengers Villa, SF Pool, 6mi to Disney!!

9.89.8 out of 10 rating
Exceptional
(12 reviews)
Windsor's Avengers Villa, SF Pool, 6mi to Disney!!
Kissimmee, FL
5% off
Price is CA $298
CA $298
CA $2,970 total
CA $2,970 total
includes taxes & fees
Image gallery for Spacious house in delightful Kissimmee with WiFi, AC

1010 out of 10 rating
Exceptional
(45 reviews)
Spacious house in delightful Kissimmee with WiFi, AC
Kissimmee, FL
5% off
Price is CA $407
CA $407
CA $4,064 total
CA $4,064 total
includes taxes & fees
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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
53 reviews(53 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
39 reviews(39 reviews)
4BR Luxury Townhome with Lazy River & Pool Close to Disney
Sleeps 10 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Windsor @ Westside 5 Bed, Private townhouse, Private Pool, Wonderful Amenities
Sleeps 10 · 5 bedrooms · 4+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
95 reviews(95 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)
Top rated rentals - Windsor at Westside
Best Place for A Family Stay
1010 out of 10
Exceptionalexceptional
145 reviews(145 reviews)
So fortunate to have found this property on VRBO. We spent 9 days with our family of 14. Everybody had tons of space. Accommodations were exceptionally clean. The decor is warm and welcoming. The outdoor set up was great for evening family meals and chats. Kitchen well stocked with pots and all dining essentials. The oversize washer is a bonus. The separate ice maker was such a bonus. Hosts were very quick to respond and kind. Definitely recommend!!
Lori B.
Stayed May 2025
Wonderful!
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Great property! Great location! Host was very responsive and the place was comfortable with everything we need.
Katlyn S.
Stayed Apr 2025
Great property!
1010 out of 10
Exceptionalexceptional
1 review(1 review)
We’ve been going to this area for at least 10 years now and this property was perfect for our group, has everything you need. The host is excellent at responding to inquiries and messages.
Daniel G.
Stayed Apr 2025
Awesome Place
1010 out of 10
Exceptionalexceptional
66 reviews(66 reviews)
We have travelled to Orlando many times. There has always been as issue, sometimes large and sometimes small. This location had NO issues what so ever. This place had everything we needed. Broom, vacuum, cleaning supplies, cooking utensils, bowls, plates cups blender and much more.
We were here for 3 weeks and had no need to buy everyday things like salt & pepper, plastic wrap and such. Rosa’s communication was great. She even checked with us a few days after arriving to ensure everything was good. It was. Highly recommend this location for a large family who wants to enjoy their holiday.
Scott J.
Stayed Mar 2024
Disney Rome Stay
1010 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
We had an enjoyable 2 week stay at the well appointed 5 bedroom 4.5 bathroom Disney Rome home which included an accessible bedroom and bathroom on the main and a handy separate half bath poolside. Eric and Lisa were wonderful hosts and were always available for any questions we had. We really enjoyed having our own pool as well as the large community resort pool complete with Lazy River that was right across the street. We appreciated the touches of Disney throughout the home including the Star Wars themed bedroom and bath upstairs.
Thank you for sharing your lovely home with us Eric and Lisa!
Cynthia and Doug Stewart
Cynthia S.
Stayed Jan 2023
Great Choice Near Disney
1010 out of 10
Exceptionalexceptional
14 reviews(14 reviews)
We chose this property because of location, ammenities, and the simplicity of furnishings ( as we had 2 young grandchildren).
We loved the place... exactly as advertised. The beds were really comfortable. The kitchen had almost everthing you need. The patio is quite private and gets the afternoon sun and looks out on a large pond. The clubhouse pool, small water park and lazy river were the hit with our young children. They keep the water at 84 all year round.
They were great and let us check in early so the grandchildren could get their afternoon naps (else we all have a bad day!) I was very appreciative that they accomodated that.
I think the place is about 20 minutes from Disney if traffic is moving well on US192. There are lots of restaurants nearby as well as large chain stores and shopping.
If you rent the condo a few small tips:
- you might want to bring a sharp knife, a can opener ( the 2 there did not work well)
- we also rented the bar b que, which they arrange from another company, we got the 2 burner...don't get a bigger one as it was a rinky dinky uneven heat thing.
It is good choice.
Blaine P.
Stayed Mar 2020
- 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, yards and more
- More for lessMore space, more privacy, more amenities — more value