A lakeside community with houses and boats.

Search Villas in Windermere

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

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
8.0 out of 10, Very good, (1 review)
"Good house for a great price. Great location. Need to change the AC more often."
United States
Mercedes
The price is £441
includes taxes & fees
28 Oct - 29 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 £423
includes taxes & fees
28 Oct - 29 Oct
The Farm House - Great Location + Pet Friendly!
A modern bathroom with two sinks, wooden cabinets, and a glass shower enclosure.

3. Family Vacation Home Near Disney With Resort Pool

Family Vacation Home Near Disney With Resort Pool
3.0 star property
Orlando
The price is £286
includes taxes & fees
2 Nov - 3 Nov
Family Vacation Home Near Disney With Resort Pool
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
9.6 out of 10, Exceptional, (33 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 £801
includes taxes & fees
28 Oct - 29 Oct
4,800 sf Estate | Pool, Lake, Weddings and Events
Interior

5. Lakefront Villa at a Prime Location

Lakefront Villa at a Prime Location
Orlando
9.2 out of 10, Wonderful, (69 reviews)
"From check in to check out everything was seamless. Very clean place and clean environment. Highly recommended."
United States
Madeen
The price is £184
includes taxes & fees
19 Nov - 20 Nov
Lakefront Villa at a Prime Location
Exterior

6. 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)
"Excellent stay and host. A short stay but we really like the home! No complaints and the host was super friendly and helpful."
United States
Joe H.
The price is £195
includes taxes & fees
1 Nov - 2 Nov
Charming Villa near Disney, pool, 4 beds, sleeps 5
A modern building with a glass facade and a large overhang.

7. 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.
SAFE QUIET PRIVATE Villa - Mins to ORL/Winter Park/Eola FREE PARKING/EV Charging
An aerial view of a resort with multiple swimming pools, a water slide, and a tower structure.

8. Amazing Spider | Disney, Slides & River

Amazing Spider | Disney, Slides & River
Kissimmee
8.0 out of 10, Very good, (1 review)
The price is £230
includes taxes & fees
29 Oct - 30 Oct
Amazing Spider | Disney, Slides & River
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 £140
includes taxes & fees
28 Oct - 29 Oct
Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
Exterior

10. Every Bedroom Has Its Own Bathroom ~ 1.4 Miles to Disney`s Animal Kingdom

Every Bedroom Has Its Own Bathroom ~ 1.4 Miles to Disney`s Animal Kingdom
Kissimmee
9.6 out of 10, Exceptional, (47 reviews)
"Great location and space and gist was great"
United States
terri
The price is £274
includes taxes & fees
3 Nov - 4 Nov
Every Bedroom Has Its Own Bathroom ~ 1.4 Miles to Disney`s Animal Kingdom
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.

11. 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 £340
includes taxes & fees
10 Nov - 11 Nov
3BR Townhouse Right in Front of Epic Universe!
Interior

12. 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 £308
includes taxes & fees
28 Oct - 29 Oct
Emerald Garden - Resort - 15 Min to Disney - Pets
A two-story residential building with a stone facade, multiple windows, and a well-maintained garden.

13. 4 BD Townhome Close to Disney!

4 BD Townhome Close to Disney!
3.0 star property
Orlando
The price is £271
includes taxes & fees
29 Oct - 30 Oct
4 BD Townhome Close to Disney!
An aerial view of a resort with multiple swimming pools, a water slide, and a tower structure.

14. 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 £243
includes taxes & fees
9 Nov - 10 Nov
Shiny Legendary | Disney, River & Slides
An aerial view of a resort with multiple swimming pools, a dock, and lush greenery.

15. 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 £257
includes taxes & fees
1 Nov - 2 Nov
Cozy 3BD Townhouse Near Disney, Encantada Resort
A two-story building with a white picket fence, a staircase, and a clear sky.

16. Completely Renovated 3/2 Close to Disney parks

Completely Renovated 3/2 Close to Disney parks
Royal Palm Bay
10.0 out of 10, Exceptional, (39 reviews)
"Located near great eateries and shops!"
United States
Kamia White K.
Completely Renovated 3/2 Close to Disney parks
A covered patio with a sofa, chairs, and a small table.

17. Stylish and Spacious Winter Park Retreat Close to Dining, Shopping and Rollins College

Stylish and Spacious Winter Park Retreat Close to Dining, Shopping and Rollins College
Winter Park
9.0 out of 10, Wonderful, (2 reviews)
"Enjoyed our stay .. was clean and had all the amenities"
United States
Ayman
The price is £300
includes taxes & fees
9 Nov - 10 Nov
Stylish and Spacious Winter Park Retreat Close to Dining, Shopping and Rollins College
A hot tub with a view of a lake and surrounding trees.

18. 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.
4BR Villa: Lakefront Retreat with Harry Potter Game Loft near Downtown Orlando
An aerial view of a lakeside resort with a swimming pool, a castle-like structure, and surrounding residential areas.

19. 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 £230
includes taxes & fees
15 Nov - 16 Nov
Beach Resort near Disney with Poolside Tike Bar
A residential property with a swimming pool, a covered patio, and a landscaped garden.

20. 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.
The price is £651
includes taxes & fees
16 Nov - 17 Nov
7BR Lakefront | Pool & Hot Tub
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
"Me gustó"
Chris 2-night trip
Posted less than an 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
232
Accommodation
10627 Villas
Lowest Price
£140
Highest Price
£801

Frequently asked questions

How much do villas in Windermere cost?
You'll pay between £140 and £801 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?
Guests recommend Villa Manuel Lakeview 3 Bedroom Condo By Redawning. Get comfortable at this 3.5-star property which offers a swimming pool and a barbecue grill. Westgate Lakes Resort And Spa is another sought-after option to check out. Unpack your suitcase at this 3.5-star stay and you'll have access to conveniences including a barbecue grill and a dock. You can pick from multiple villas in Windermere with a total average guest review rating of 9.5.
How many villas are there in Windermere?
Reclaim your holiday days and pick from 10627 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.
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.

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