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Compare Villas in Windermere with updated reviews, rates, and availability.

Lakeview Luxury Villa with Everything

9.8 out of 10, Exceptional, (314)
"The house was immaculate, beautifully decorated and in a peaceful gated community. We loved every moment of the rental!! We have never had had such a seamless check-in and check-out. Without a doubt, we WILL be back!! "
Lakeview Luxury Villa with Everything

Modern Luxury Villa with Everything

9.8 out of 10, Exceptional, (364)
"Fun property"
Modern Luxury Villa with Everything

Lakeview Luxury Villa with Everything

10.0 out of 10, Exceptional, (68)
"The house was great plenty big for our family with 8 adults and 7 children. The only issue was the weather it was cold but the kids still all had a great time in the heated pool and game room. "
Lakeview Luxury Villa with Everything

Ultimate Lakeview Villa with Everything!

9.4 out of 10, Exceptional, (95)
"The house was worked out perfectly for our family stay. We had a broad range of ages from 9 months to 8 years old and there was something for everyone.The house was clean and well appointed.The host was very responsive to all of our requests. We would definitely come back."
Ultimate Lakeview Villa with Everything!

Heavenly 5 Bedroom, 6 Bathroom Private Pool Home with Beautiful Lakeview in Gated Resort!

9.2 out of 10, Wonderful, (9)
"Loved this very clean, well managed property, we plan on booking again next year"
Heavenly 5 Bedroom, 6 Bathroom Private Pool Home with Beautiful Lakeview in Gated Resort!

Large Margaritaville Villa w/ Private Pool + View

4.0 star property
10.0 out of 10, Exceptional, (4)
"Great property, comfortable beds, kitchen equipped with everything you need, washer and dryer, dinning table for 10 people, every room with tv, terrace tv, bathroom and small pool but very pleasant. No rooms on first floor. 3 rooms on second floor and 2 rooms on third floor. I will stay again."
Large Margaritaville Villa w/ Private Pool + View

*Nice Greenbackyard*Cozy 6BR Windsor Hills Pool Villa,2 Miles To Disney

9.2 out of 10, Wonderful, (60)
"This was a big house with more then enough room for all of my family. There were small things wrong such as lots of little bugs (It's Florida, it happens) and the pool turning green overnight, but the owners were VERY responsive when I contacted them about it which I appreciated. We loved sitting outside by the pool and just soaking in the Florida sunshine. This could be a super nice property if a little money was thrown in to do some updates but overall we really enjoyed our stay. The main...
*Nice Greenbackyard*Cozy 6BR Windsor Hills Pool Villa,2 Miles To Disney

Beautiful Spacious 3 Bedroom Villa with Private Pool and Wonderful Lake View

8.6 out of 10, Excellent, (83)
"We have stayed at this property 3 times. The host is amazing, very responsive and kind. The location is great and the home is a great value. "
Beautiful Spacious 3 Bedroom Villa with Private Pool and Wonderful Lake View

Ultimate Lakeview Villa with Everything!

9.8 out of 10, Exceptional, (332)
"The property, neighborhood, location, and communication with the host were fantastic. There were no unwelcome surprises and the process of checking in and out couldn’t have been easier. Will definitely use one of their properties again in the future. "
Ultimate Lakeview Villa with Everything!

Villa in Kissimmee next to Disney!

8.0 out of 10, Very Good, (16)
"Nothing really to complain about, a little dusty and could use a deep cleaning for the carpets"
Villa in Kissimmee next to Disney!

Modern Luxury Villa with Everything

9.6 out of 10, Exceptional, (207)
"The house was just as advertised. The gate check in was a little tough, but everything else was great"
Modern Luxury Villa with Everything

Modern villa with patio, grill, central AC, WiFi, shared pool, tennis, & gym

9.4 out of 10, Exceptional, (6)
"We would return again"
Modern villa with patio, grill, central AC, WiFi, shared pool, tennis, & gym

Champions Gate Luxury 6 Bedroom Resort Villa With Spa and Games Room on Golf Course community

8.6 out of 10, Excellent, (33)
"Lovely villa, excellent area to stay, we loved the club house and all the amenities. Would definitely stay again. Any problems we had were sorted quickly, excellent service. "
Champions Gate Luxury 6 Bedroom Resort Villa With Spa and Games Room on Golf Course community

Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills

10.0 out of 10, Exceptional, (168)
"Owners and Property management company were awesome as we booked for a convention last minute. We got lucky those specific dates were open because it is very booked in the future.Great value with three king bedrooms so lots of room we used and three other rooms. Lots of cool fun things in villa to entertain adults and two very cool themed kids rooms and game room."
Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills

Experience Kissimmee living near vibrant Old Town

9.6 out of 10, Exceptional, (27)
"Beautiful and just as the photos showed. Plenty of room. "
Experience Kissimmee living near vibrant Old Town

Private Heated Pool! Only 8 miles to Disney! Gated Community

10.0 out of 10, Exceptional, (49)
"House is clean. Development is quiet. Hosts were generous with pool heat even though it was quite cold outside. They were also generous with household items. It was a very nice experience."
Private Heated Pool! Only 8 miles to Disney! Gated Community

Beautiful 12 bedroom 11 Bathroom house Bella Vida Resort Villa

8.6 out of 10, Excellent, (4)
"The house was great and fit our needs very well. Large kitchen with 2 refrigerators and 2 dishwashers, as well as well-stocked cupboards with dishes. The dining and living room area was comfortable for all of us. The game room was wonderful for the kids and we all enjoyed the pool and hot tub. Located close to many parks and shopping areas. We enjoyed the house very much! "
Beautiful 12 bedroom 11 Bathroom house Bella Vida Resort Villa

4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee Us192

10.0 out of 10, Exceptional, (272)
"Our family travels to Orlando a lot and this property was the best we've stayed at in terms of location to the parks. It took us only 15 minutes to get to each Disney park! It was very clean and had plenty of space. We didn't use the community amenities much, but they seemed very nice. Robert and Louise were very responsive to any questions we had. I wouldn't hesitate to stay here again! Thank you, Robert and Louise!"
4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee Us192

South Facing Pool and spa on Water Conservation Area in Gated Community

10.0 out of 10, Exceptional, (9)
"This was a very spacious house that was clean and had all the essentials for our trip. The neighborhood was very nice and the area where the home is located was quiet with nice views of the lake. The pool area was private and had plenty of room to relax whether you were swimming or just relaxing outside. No outdoor tv, but that was the only thing we would have changed. We really enjoyed the pool table upstairs and game room in the garage for extra free entertainment while we were there. This was...
South Facing Pool and spa on Water Conservation Area in Gated Community

Luxury 7 bedroom Villa on the gated Bellavida Resort, close to everything Disney

2.0 star property
9.6 out of 10, Exceptional, (4)
"We were there for a work conference and church the house was perfect for our group. Our host was outstanding with all the info we needed for a great stay."
Luxury 7 bedroom Villa on the gated Bellavida Resort, close to everything Disney
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Windermere

The View Studio Suites and Event Venue

3.5 star property
8.4 out of 10, Very Good, (784)
"Host Gina was exceptionally helpful "
The price is AED 298
AED 335 total
includes taxes & fees
3 Feb - 4 Feb
The View Studio Suites and Event Venue

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1179)
"This is our 3rd time staying here. We did not love this cottage as much as we did the others. Although each room had a bathroom there was not one outside the bedrooms. We had 6 people and there was limited seating & small living room area The master bathroom shower leaked all over the floor Wish we were told there was a hot tub do we could have brought bathing suits We liked that it was less than a 10 minute walk to the Salty Rim and the shuttle to the promenade was very quick & convenient"
Margaritaville Resort Orlando Cottages by Rentyl

Lake Buena Vista Resort Village & Spa

4.0 star property
8.4 out of 10, Very Good, (8336)
"Plenty of parking. Separate bedrooms it was to cool to use the outdoor pools"
Lake Buena Vista Resort Village & Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much do villas in Windermere cost?
You can expect to pay between and per night for villas in Windermere. Whatever your budget, a perfect stay is just a click away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best villas in Windermere?
Select from multiple villas in Windermere with a total average guest review rating of . Westgate Lakes Resort And Spa comes highly recommended by travelers. This 3.5-star property features an outdoor entertainment area and a barbecue grill. Villa Manuel Lakeview 3 Bedroom Condo By Redawning is another popular option. It has a 3.5-star rating and conveniences such as a swimming pool and a barbecue grill.
How many villas are there in Windermere?
Use up your vacation days and pick from villas in Windermere. For a family trip, a couple’s getaway or anything in between, Expedia can help you find the right place in just a click or two.
Why book your villa in Windermere with Expedia?
Reserving a villa in Windermere is as easy as deciding on your travel dates and picking an option that has what you need. Want something luxurious or affordable, or a property that also comes with a kitchenette? Use Expedia’s search filters to narrow your results and find your ideal match.
How can I find cheap villas in Windermere?
Expedia is here to help you track down cheap villas in Windermere. Use our handy filter tool to choose amenities, star rating and budget to refine your search and find a fantastic place to stay in just a few clicks.