A lakeside community with houses and boats.

Search Villas in Windermere

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Windermere villas

BBQ/picnic Area

1. Rustic Hideaway - Great Location + Pet Friendly!

Rustic Hideaway - Great Location + Pet Friendly!
4.0 star property
Windermere
The price is HK$1,130
HK$4,632 total
includes taxes & fees
12 Oct - 13 Oct
Rustic Hideaway - Great Location + Pet Friendly!
A two-story house with a paved driveway and a lawn.

2. The Farm House - Great Location + Pet Friendly!

The Farm House - Great Location + Pet Friendly!
4.0 star property
Windermere
The price is HK$1,256
HK$4,447 total
includes taxes & fees
15 Oct - 16 Oct
The Farm House - Great Location + Pet Friendly!
A hotel with a modern architectural design, featuring a large entrance with a covered walkway, palm trees, and a clear blue sky.

3. Fully-Equipped Villa Next to Disney!

Fully-Equipped Villa Next to Disney!
Kissimmee
9.2 out of 10, Wonderful, (85 reviews)
"Enjoyed a 5 day trip with my daughter. Great location, felt safe, lots of dining options and communication was good. I had everything I needed but mainly ate at restaurants as we were out and about."
United States
Shari W.
The price is HK$651
HK$1,580 total
includes taxes & fees
13 Oct - 14 Oct
Fully-Equipped Villa Next to Disney!
A poolside area with a covered seating area, a pool, and a view of a body of water.

4. 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 HK$3,390
HK$8,769 total
includes taxes & fees
19 Oct - 20 Oct
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.

5. 3BR Townhouse Right in Front of Epic Universe!

3BR Townhouse Right in Front of Epic Universe!
Orlando
9.6 out of 10, Exceptional, (16 reviews)
"Easy access for all we did the week we stayed. Great rooms, it was wonderful to be so comfortable."
United States
Hal J.
The price is HK$1,411
HK$3,439 total
includes taxes & fees
11 Nov - 12 Nov
3BR Townhouse Right in Front of Epic Universe!
A modern building with a glass facade and a large overhang.

6. 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 HK$934
HK$1,375 total
includes taxes & fees
25 Oct - 26 Oct
SAFE QUIET PRIVATE Villa - Mins to ORL/Winter Park/Eola FREE PARKING/EV Charging
Exterior

7. 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 HK$816
HK$2,940 total
includes taxes & fees
14 Oct - 15 Oct
Location! 1.4 miles to Disney - Orlando Family Home
A two-story house with a front porch, a mailbox, and a well-maintained garden with various plants and a palm tree.

8. Upstay Modern 3BR Townhome With Pool Near Disney

Upstay Modern 3BR Townhome With Pool Near Disney
3.5 star property
Kissimmee
The price is HK$636
HK$2,049 total
includes taxes & fees
2 Nov - 3 Nov
Upstay Modern 3BR Townhome With Pool Near Disney
Exterior

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

Charming Villa near Disney, pool, 4 beds, sleeps 5
Vacation Village
8.8 out of 10, Excellent, (5 reviews)
"Host was terrific. Vacation Village was a nice neighborhood. Close to the state park for our event. "
United States
Trey C.
The price is HK$902
HK$1,974 total
includes taxes & fees
18 Oct - 19 Oct
Charming Villa near Disney, pool, 4 beds, sleeps 5
A large hotel with a central swimming pool, multiple guest rooms, and a tennis court.

10. Spacious 2BR Villa Near Disney

Spacious 2BR Villa Near Disney
Kissimmee
9.2 out of 10, Wonderful, (5 reviews)
The price is HK$2,188
HK$3,341 total
includes taxes & fees
18 Oct - 19 Oct
Spacious 2BR Villa Near Disney
Interior

11. Emerald Garden - Resort - 15 Min to Disney - Pets

Emerald Garden - Resort - 15 Min to Disney - Pets
3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is HK$891
HK$3,232 total
includes taxes & fees
12 Oct - 13 Oct
Emerald Garden - Resort - 15 Min to Disney - Pets
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 HK$1,554
HK$4,403 total
includes taxes & fees
12 Oct - 13 Oct
4BR Villa: Lakefront Retreat with Harry Potter Game Loft near Downtown Orlando
A modern kitchen with a bar area, a dining space, and a living area with a fireplace.

13. 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, (32 reviews)
"Very nice place and hope to stay there again someday"
United States
Wilbur B.
The price is HK$1,759
HK$4,159 total
includes taxes & fees
12 Oct - 13 Oct
At Lakes Upscale Villa/Next to Downtown Orlando
An aerial view of a resort with multiple swimming pools, a water slide, and a tower structure.

14. Amazing Spider | Disney, Slides & River

Amazing Spider | Disney, Slides & River
Kissimmee
8.0 out of 10, Very good, (1 review)
The price is HK$521
HK$2,422 total
includes taxes & fees
13 Oct - 14 Oct
Amazing Spider | Disney, Slides & River
An indoor swimming pool with two lounge chairs, a glass-enclosed patio, and a view of trees and buildings.

15. 17319 4BR Townhouse Heated Pool near Disney

17319 4BR Townhouse Heated Pool near Disney
Clermont
The price is HK$941
HK$2,736 total
includes taxes & fees
26 Oct - 27 Oct
17319 4BR Townhouse Heated Pool near Disney
A residential neighborhood with houses featuring front yards, pathways, and small trees.

16. Waterfront 3BR Pool Cottage at Margaritaville Orlando - Near Disney

Waterfront 3BR Pool Cottage at Margaritaville Orlando - Near Disney
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay overall! The house was very clean, comfortable, and exactly what we needed for our vacation. The pool was fantastic and definitely one of the highlights of our trip! The host was very responsive, kind, communicative, and genuinely wanted to make sure we had a good experience. When an issue came up during our stay, they responded quickly and worked with us to try to find a solution, which we really appreciated. Overall, this is a great place to stay. We enjoyed our time...
United States
Monique
The price is HK$2,511
HK$5,115 total
includes taxes & fees
11 Nov - 12 Nov
Waterfront 3BR Pool Cottage at Margaritaville Orlando - Near Disney
A modern two-story house with a white exterior, a brick accent wall, and a front entrance with a glass door.

17. 17244 4BR Townhouse Heated Pool near Disney

17244 4BR Townhouse Heated Pool near Disney
Clermont
9.0 out of 10, Wonderful, (2 reviews)
"Great property! Just be aware that you will need to bring more trash bags and cleaning supplies if you intend to stay more than a few days. They say it in the listing, but still a hassle. Other than that the house was awesome "
United States
Philip N.
The price is HK$941
HK$2,744 total
includes taxes & fees
21 Oct - 22 Oct
17244 4BR Townhouse Heated Pool near Disney
An outdoor lounge area with multiple seating options, ceiling fans, and large windows offering views of palm trees and a beach.

18. Upstay Modern Solara Retreat w Games Room & Pool

Upstay Modern Solara Retreat w Games Room & Pool
3.0 star property
Kissimmee
The price is HK$997
HK$2,815 total
includes taxes & fees
18 Oct - 19 Oct
Upstay Modern Solara Retreat w Games Room & Pool
An aerial view of a resort with multiple swimming pools, a water slide, and a tower structure.

19. 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 HK$521
HK$2,415 total
includes taxes & fees
19 Oct - 20 Oct
Shiny Legendary | Disney, River & Slides
A residential complex with multiple houses, a parking area, and a swimming pool.

20. 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 HK$594
HK$3,822 total
includes taxes & fees
12 Oct - 13 Oct
Storey Lake Resort~Heated Pool~Brand New~Designer
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windermere Hotel Reviews

Universal's Endless Summer Resort - Dockside Inn and Suites

Universal's Endless Summer Resort - Dockside Inn and Suites

10/10 Excellent
"Clean rooms great staff"
leah dell 3-night trip
Posted 2 hours ago
Universal's Endless Summer Resort - Dockside Inn and Suites

Find out more about Windermere

Windermere Villas information

Number of reviews
166
Accommodation
9865 Villas
Lowest Price
HK$1,375
Highest Price
HK$8,769

Frequently asked questions

How much do villas in Windermere cost?
You'll pay between HK$1,375 and HK$8,769 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 9.7. 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 9865 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.

Explore a world of travel with Expedia