A lakeside community with houses and boats.

Villas in Windermere

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Check prices for these dates

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

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
$531 nightly
The price is $589
Oct 5 - Oct 6
Total with taxes and fees
Rustic Hideaway - Great Location + Pet Friendly!
A poolside area with a covered seating area, a pool, and a view of a body of water.

2. 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.
$914 nightly
The price is $1,015
Oct 5 - Oct 6
Total with taxes and fees
4,800 sf Estate | Pool, Lake, Weddings and Events
Exterior

3. 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.
$232 nightly
The price is $255
Oct 4 - Oct 5
Total with taxes and fees
Charming Villa near Disney, pool, 4 beds, sleeps 5
An aerial view of a resort with multiple swimming pools, a water slide, and a tower structure.

4. Amazing Spider | Disney, Slides & River

Amazing Spider | Disney, Slides & River
Kissimmee
8.0 out of 10, Very good, (1 review)
$271 nightly
The price is $306
Oct 6 - Oct 7
Total with taxes and fees
Amazing Spider | Disney, Slides & River
A modern building with a glass facade and a large overhang.

5. 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.
$158 nightly
The price is $175
Oct 25 - Oct 26
Total with taxes and fees
SAFE QUIET PRIVATE Villa - Mins to ORL/Winter Park/Eola FREE PARKING/EV Charging
The exterior of Altamonte Mall with a large green sign, palm trees, and a curved entrance.

6. 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
$166 nightly
The price is $184
Oct 3 - Oct 4
Total with taxes and fees
Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
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
$350 nightly
The price is $391
Oct 21 - Oct 22
Total with taxes and fees
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
$243 nightly
The price is $276
Oct 6 - Oct 7
Total with taxes and fees
Upstay Modern 3BR Townhome With Pool Near Disney
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.

9. 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.
$414 nightly
The price is $435
Oct 4 - Oct 5
Total with taxes and fees
3BR Townhouse Right in Front of Epic Universe!
An aerial view of a resort with multiple swimming pools, a water slide, and a tower structure.

10. 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.
$271 nightly
The price is $306
Oct 8 - Oct 9
Total with taxes and fees
Shiny Legendary | Disney, River & Slides
A two-story building with a symmetrical facade, a central entrance with a door, and a small porch area.

11. Lazy River~Tiki Bar~Pool~Hot Tub~Themed~Disney

Lazy River~Tiki Bar~Pool~Hot Tub~Themed~Disney
Regal Palms
$565 nightly
The price is $568
Oct 7 - Oct 8
Total with taxes and fees
Lazy River~Tiki Bar~Pool~Hot Tub~Themed~Disney
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)
$397 nightly
The price is $412
Oct 4 - Oct 5
Total with taxes and fees
Emerald Garden - Resort - 15 Min to Disney - Pets
An aerial view of a resort with multiple swimming pools, a dock, and lush greenery.

13. 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.
$397 nightly
The price is $443
Oct 6 - Oct 7
Total with taxes and fees
Cozy 3bd Townhouse | Near Disney| Encantada Resort
A covered swimming pool with a view of a grassy area and trees.

14. 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.
$536 nightly
The price is $597
Oct 6 - Oct 7
Total with taxes and fees
7BR Lakefront | Pool & Hot Tub
A modern two-story house with a white exterior, a brick accent wall, and a front entrance with a glass door.

15. 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.
$315 nightly
The price is $346
Oct 18 - Oct 19
Total with taxes and fees
17244 4BR Townhouse Heated Pool near Disney
A residential complex with multiple houses, a parking area, and a swimming pool.

16. 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.
$464 nightly
The price is $489
Oct 12 - Oct 13
Total with taxes and fees
Storey Lake Resort~Heated Pool~Brand New~Designer
An aerial view of a residential area with a large swimming pool complex, surrounded by single-family homes and a body of water.

17. Family 5BR w/ Pool & Grill Near Disney Magic

Family 5BR w/ Pool & Grill Near Disney Magic
Kissimmee
$541 nightly
The price is $604
Oct 4 - Oct 5
Total with taxes and fees
Family 5BR w/ Pool & Grill Near Disney Magic
A modern building with a stone facade, multiple windows, and a parking lot.

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

Upstay Pristine 3BR Home With Private Pool & BBQ
3.5 star property
Clermont
$253 nightly
The price is $280
Oct 8 - Oct 9
Total with taxes and fees
Upstay Pristine 3BR Home With Private Pool & BBQ
A covered patio with a sofa, chairs, and a small table.

19. 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
$299 nightly
The price is $299
Oct 4 - Oct 5
Total with taxes and fees
Stylish and Spacious Winter Park Retreat Close to Dining, Shopping and Rollins College
A balcony with two blue cushioned chairs, a glass door leading to a bedroom, and a view of a grassy area and buildings in the distance.

20. Stylish 3BR Condo Championsgate w Water Park

Stylish 3BR Condo Championsgate w Water Park
3.0 star property
Davenport
$346 nightly
The price is $393
Oct 7 - Oct 8
Total with taxes and fees
Stylish 3BR Condo Championsgate w Water Park
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

Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent
"We really enjoyed our stay here. The breakfast was top tier and the staff were so friendly. Will definitely be back!"
LeighAnn 4-night trip
Posted 6 hours ago
Drury Plaza Hotel Orlando - Disney Springs Area

Find out more about Windermere

Windermere Villas information

Number of reviews
171
Accommodation
9824 Villas
Lowest Price
$175
Highest Price
$1,015

Frequently asked questions

How much do villas in Windermere cost?
You'll pay between $175 and $1,015 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 vacation days and pick from 9824 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 cozy 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 favorite among travelers. 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. Vacationing 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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