A lakeside community with houses and boats.

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Windermere villas

1. Rustic Hideaway - Great Location + Pet Friendly!

Rustic Hideaway - Great Location + Pet Friendly!
4.0 star property
Windermere
The price is €492
includes taxes & fees
29 Sept - 30 Sept
Rustic Hideaway - Great Location + Pet Friendly!
A building with a red-tiled roof, surrounded by palm trees and well-maintained grass.

2. Cozy One Bedroom Lakefront Villa Close to the Attractions

Cozy One Bedroom Lakefront Villa Close to the Attractions
Orlando
9.0 out of 10, Wonderful, (47 reviews)
"The location was great close to airport , universal, Disney it was right in the middle. Loved it "
United States
Larry J.
The price is €199
includes taxes & fees
2 Oct - 3 Oct
Cozy One Bedroom Lakefront Villa Close to the Attractions
A modern building with a glass facade and a large overhang.

3. SAFE QUIET PRIVATE Villa - Mins to ORL/Winter Park/Eola FREE PARKING/EV Charging

SAFE QUIET PRIVATE Villa - Mins to ORL/Winter Park/Eola FREE PARKING/EV Charging
College Park
10.0 out of 10, Exceptional, (30 reviews)
"Great space! Was very comfortable "
United States
Judah E.
The price is €158
includes taxes & fees
28 Oct - 29 Oct
SAFE QUIET PRIVATE Villa - Mins to ORL/Winter Park/Eola FREE PARKING/EV Charging

4. Charming Villa near Disney, pool, 4 beds, sleeps 5

Charming Villa near Disney, pool, 4 beds, sleeps 5
Vacation Village
8.6 out of 10, Excellent, (4 reviews)
"Host was terrific. Vacation Village was a nice neighborhood. Close to the state park for our event. "
United States
Trey C.
Charming Villa near Disney, pool, 4 beds, sleeps 5
A poolside area with a covered seating area, a pool, and a view of a body of water.

5. 4,800 sf Estate | Pool, Lake, Weddings and Events

4,800 sf Estate | Pool, Lake, Weddings and Events
Orlando
9.8 out of 10, Exceptional, (32 reviews)
"Loved that Lake Lucy was pet friendly so our dogs could be a part of our wedding day! The house property was amazing and we wish we could have stayed longer!"
United States
Krysta P.
The price is €889
includes taxes & fees
29 Sept - 30 Sept
4,800 sf Estate | Pool, Lake, Weddings and Events
A modern living room with a brown leather sofa, a glass coffee table, and blue chairs. There is a dining area with a glass table and white plates. A chandelier hangs from the ceiling, and a clock is on the wall.

6. 3BR Townhouse Right in Front of Epic Universe!

3BR Townhouse Right in Front of Epic Universe!
Orlando
9.6 out of 10, Exceptional, (15 reviews)
"Easy access for all we did the week we stayed. Great rooms, it was wonderful to be so comfortable."
United States
Hal J.
3BR Townhouse Right in Front of Epic Universe!
A modern multi-story residential building with a symmetrical facade, stone accents, and a central entrance.

7. Contemporary 4BR Townhome With Pool & Themed Rooms

Contemporary 4BR Townhome With Pool & Themed Rooms
3.5 star property
Clermont
10.0 out of 10, Exceptional, (1 review)
"Even better than what is shown"
United States
Malyjah
The price is €286
includes taxes & fees
29 Sept - 30 Sept
Contemporary 4BR Townhome With Pool & Themed Rooms
A covered swimming pool with a view of a grassy area and trees.

8. 7BR Lakefront | Pool & Hot Tub

7BR Lakefront | Pool & Hot Tub
Edgewood
9.8 out of 10, Exceptional, (21 reviews)
"Check in was very easy and the location was great, close to everything we wanted to do.The property had lots to offer and was in a nice quiet neighborhood."
United States
Omer H.
7BR Lakefront | Pool & Hot Tub
The exterior of Altamonte Mall with a large green sign, palm trees, and a curved entrance.

9. Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix

Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
Altamonte Springs
9.4 out of 10, Exceptional, (8 reviews)
"Enjoyed my stay, was super quiet, and very conveniently located to everywhere I needed to go in Seminole County. The host was great with communication and provided everything I needed to have a great stay."
United States
Brian
The price is €165
includes taxes & fees
29 Sept - 30 Sept
Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
An aerial view of a resort with multiple swimming pools, a dock, and lush greenery.

10. Cozy 3bd Townhouse | Near Disney| Encantada Resort

Cozy 3bd Townhouse | Near Disney| Encantada Resort
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"I was looking for a place to escape for a few days while getting my bathroom redone and the property checked all of the boxes. My wife was able to get some work done, my dog had more than enough space, and the location is minutes from the amusement parks and tons of restaurants.The property is gated, clean, and has multiple bedrooms and bathrooms for the larger families that need it. The host was more than attentive. Even when I was having issues with the television, he responded to my message...
United States
LEONARD W.
The price is €368
includes taxes & fees
29 Sept - 30 Sept
Cozy 3bd Townhouse | Near Disney| Encantada Resort
A modern kitchen with a bar area, a dining space, and a living area with a fireplace.

11. At Lakes Upscale Villa/Next to Downtown Orlando

At Lakes Upscale Villa/Next to Downtown Orlando
Lake Davis - Greenwood
10.0 out of 10, Exceptional, (31 reviews)
"Very nice place and hope to stay there again someday"
United States
Wilbur B.
At Lakes Upscale Villa/Next to Downtown Orlando
A hot tub with a view of a lake and surrounding trees.

12. 4BR Villa: Lakefront Retreat with Harry Potter Game Loft near Downtown Orlando

4BR Villa: Lakefront Retreat with Harry Potter Game Loft near Downtown Orlando
Orlando
10.0 out of 10, Exceptional, (4 reviews)
"Overall it was great stay. Initially there was an issue with the door when we checked in, but the host fixed it write away. The house was very clean and had everything we needed plus more. I would definitely book again."
United States
Silvia R.
The price is €520
includes taxes & fees
29 Sept - 30 Sept
4BR Villa: Lakefront Retreat with Harry Potter Game Loft near Downtown Orlando
An aerial view of a resort with multiple swimming pools, a water slide, and a tower structure.

13. Shiny Legendary | Disney, River & Slides

Shiny Legendary | Disney, River & Slides
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Had some confusion with the address but the host was super quick to respond, apologize, and fix the problem. Great location. Super cute rooms. Clean. Host had lots of essentials already at the house for us. Any question or concern we had was responded to quickly and thoroughly. "
United States
Aren B.
The price is €267
includes taxes & fees
1 Oct - 2 Oct
Shiny Legendary | Disney, River & Slides
An aerial view of a resort with a swimming pool, sun loungers, and a red-roofed building.

14. Paradise Found: Luxurious 5-Bedroom / 3 Bath Retreat with Pool in Emerald Island

Paradise Found: Luxurious 5-Bedroom / 3 Bath Retreat with Pool in Emerald Island
Kissimmee
8.6 out of 10, Excellent, (14 reviews)
"Beautiful resort, great location"
United States
Sandra A.
The price is €433
includes taxes & fees
29 Sept - 30 Sept
Paradise Found: Luxurious 5-Bedroom / 3 Bath Retreat with Pool in Emerald Island

15. Location! 1.4 miles to Disney - Orlando Family Home

Location! 1.4 miles to Disney - Orlando Family Home
Kissimmee
9.6 out of 10, Exceptional, (47 reviews)
"Great location and space and gist was great"
United States
terri
The price is €335
includes taxes & fees
29 Sept - 30 Sept
Location! 1.4 miles to Disney - Orlando Family Home
An aerial view of a lakeside resort with a swimming pool, a castle-like structure, and surrounding residential areas.

16. Beach Resort near Disney with Poolside Tike Bar

Beach Resort near Disney with Poolside Tike Bar
Bahama Bay
9.6 out of 10, Exceptional, (4 reviews)
"Love it"
United States
Jerome S.
The price is €275
includes taxes & fees
29 Sept - 30 Sept
Beach Resort near Disney with Poolside Tike Bar
A modern building with a stone facade, multiple windows, and a parking lot.

17. Upstay Pristine 3BR Home With Private Pool & BBQ

Upstay Pristine 3BR Home With Private Pool & BBQ
3.5 star property
Clermont
The price is €257
includes taxes & fees
29 Sept - 30 Sept
Upstay Pristine 3BR Home With Private Pool & BBQ
A residential complex with multiple houses, a parking area, and a swimming pool.

18. Storey Lake Resort~Heated Pool~Brand New~Designer

Storey Lake Resort~Heated Pool~Brand New~Designer
Kissimmee
10.0 out of 10, Exceptional, (7 reviews)
"We had a great stay. Host was very attentive and responded back quickly anytime we had a question before or during our stay. Resort amenities were wonderful and location was great! We would stay again! "
United States
Amber K.
The price is €433
includes taxes & fees
12 Oct - 13 Oct
Storey Lake Resort~Heated Pool~Brand New~Designer
A clear, enclosed swimming pool with a 5 FT depth marker, surrounded by a metal frame and glass walls, with a grassy area and buildings in the background.

19. Beautiful 7 Bedroom Villa - 4 King Suites, 5.5 Bath, Sleeps 16!

Beautiful 7 Bedroom Villa - 4 King Suites, 5.5 Bath, Sleeps 16!
Kissimmee
8.6 out of 10, Excellent, (90 reviews)
"It was a very nice house my family and I really enjoyed it and made beautiful memories the property manager was very quick to get back with me and helpful, it was very close and convenient to the parks. Would love to stay here again."
United States
Cheryl D.
Beautiful 7 Bedroom Villa - 4 King Suites, 5.5 Bath, Sleeps 16!
An aerial view of a resort with multiple swimming pools, a water slide, and a tower structure.

20. Amazing Spider | Disney, Slides & River

Amazing Spider | Disney, Slides & River
Kissimmee
8.0 out of 10, Very good, (1 review)
The price is €296
includes taxes & fees
25 Oct - 26 Oct
Amazing Spider | Disney, Slides & River
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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Top Windermere Hotel Reviews

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

10/10 Excellent
"Clean room awesome breakfast i would absolutely stay here again"
Deidra 2-night trip
Posted 1 hour ago
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Find out more about Windermere

Windermere Villas information

Number of reviews
310
Accommodation
8387 Villas
Lowest Price
€158
Highest Price
€889

Frequently asked questions

How much do villas in Windermere cost?
You'll pay between €158 and €889 per night for villas in Windermere. Whatever your budget, an epic escape is only a few clicks 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?
Windermere has multiple villas with a total average guest review rating of 9.6. Villa Manuel Lakeview 3 Bedroom Condo By Redawning is a popular option with Expedia guests. Visitors staying at this 3.5-star property will have use of a barbecue grill and a swimming pool. Westgate Lakes Resort And Spa is another much-loved stay. This 3.5-star villa offers an outdoor entertainment area and a cafe, among other conveniences.
How many villas are there in Windermere?
Reclaim your holiday days and pick from 8387 villas in Windermere. For a family adventure, a romantic break or anything in between, Expedia can help you find the right place in a few simple clicks.
Are there any family-friendly villas in Windermere?
Get cosy at Villa Manuel Lakeview 3 Bedroom Condo By Redawning, a 3.5-star option only a quick drive from town. Amenities here include a playground and a barbecue grill. Another family-friendly getaway is Westgate Lakes Resort And Spa. A barbecue grill and a cafe help make this 3.5-star villa a favourite among travellers. Once you've checked in and unpacked your things, there are tons of family-friendly attractions to visit around Windermere. Walt Disney World® Resort and Universal Studios Florida guarantee fun for all ages.
Why book your villa in Windermere with Expedia?
With Expedia, it's easy to find your dream villa in Windermere. Holidaying with the kids? Take advantage of our filters to search for stays with amenities like free WiFi. If you have a budget, select how much you're willing to spend and the star rating of the property. We'll help you find the perfect place that suits your taste and style.
How can I find cheap villas in Windermere?
A great way to score cheap villas in Windermere is with Expedia's filter tool. Tailor your search results by amenities, budget and star rating to discover unbeatable deals in just a few clicks.
What is there to do near my villa in Windermere?
Once you've unpacked your suitcases, set out and discover the incredible things Windermere has to offer. Isleworth Golf and Country Club is a top attraction to add to your must-see list.