A lakeside community with houses and boats.

Villas in Windermere

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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
$531 nightly
The price is $589
Oct 18 - Oct 19
Total with taxes and fees
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 Farm House - Great Location + Pet Friendly!
A poolside area with a covered seating area, a pool, and a view of a body of water.

3. 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.
$948 nightly
The price is $1,053
Oct 19 - Oct 20
Total with taxes and fees
4,800 sf Estate | Pool, Lake, Weddings and Events
Interior

4. 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
$215 nightly
The price is $239
Oct 20 - Oct 21
Total with taxes and fees
Lakefront Villa at a Prime Location
Exterior

5. 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.
$232 nightly
The price is $255
Oct 18 - Oct 19
Total with taxes and fees
Charming Villa near Disney, pool, 4 beds, sleeps 5
A two-story house with a front porch, a mailbox, and a well-maintained garden with various plants and a palm tree.

6. Upstay Modern 3BR Townhome With Pool Near Disney

Upstay Modern 3BR Townhome With Pool Near Disney
3.5 star property
Kissimmee
$235 nightly
The price is $266
Nov 4 - Nov 5
Total with taxes and fees
Upstay Modern 3BR Townhome With Pool Near Disney
An aerial view of a resort with multiple swimming pools, a water slide, and a tower structure.

7. Amazing Spider | Disney, Slides & River

Amazing Spider | Disney, Slides & River
Kissimmee
8.0 out of 10, Very good, (1 review)
$273 nightly
The price is $309
Oct 27 - Oct 28
Total with taxes and fees
Amazing Spider | Disney, Slides & River
A modern building with a glass facade and a large overhang.

8. 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
Exterior

9. 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
$319 nightly
The price is $356
Oct 19 - Oct 20
Total with taxes and fees
Location! 1.4 miles to Disney - Orlando Family Home
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.

10. 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.
$398 nightly
The price is $419
Oct 18 - Oct 19
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.

11. 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.
$272 nightly
The price is $308
Oct 19 - Oct 20
Total with taxes and fees
Shiny Legendary | Disney, River & Slides
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 17 - Oct 18
Total with taxes and fees
Emerald Garden - Resort - 15 Min to Disney - Pets
The exterior of Altamonte Mall with a large green sign, palm trees, and a curved entrance.

13. 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
$175 nightly
The price is $194
Nov 8 - Nov 9
Total with taxes and fees
Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
An aerial view of a resort with multiple swimming pools, a dock, and lush greenery.

14. 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.
$306 nightly
The price is $342
Oct 21 - Oct 22
Total with taxes and fees
Cozy 3bd Townhouse | Near Disney| Encantada Resort
A hot tub with a view of a lake and surrounding trees.

15. 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.
$496 nightly
The price is $551
Oct 19 - Oct 20
Total with taxes and fees
4BR Villa: Lakefront Retreat with Harry Potter Game Loft near Downtown Orlando
A modern building with a stone facade, multiple windows, and a parking lot.

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

Upstay Pristine 3BR Home With Private Pool & BBQ
3.5 star property
Clermont
$264 nightly
The price is $293
Oct 18 - Oct 19
Total with taxes and fees
Upstay Pristine 3BR Home With Private Pool & BBQ
A residential area with multiple houses, a central building with a swimming pool, and a curved road layout.

17. The ideal getaway II

The ideal getaway II
Kissimmee
$288 nightly
The price is $328
Oct 23 - Oct 24
Total with taxes and fees
The ideal getaway II
An indoor swimming pool with two lounge chairs, a glass-enclosed patio, and a view of trees and buildings.

18. 17319 4BR Townhouse Heated Pool near Disney

17319 4BR Townhouse Heated Pool near Disney
Clermont
$318 nightly
The price is $349
Oct 26 - Oct 27
Total with taxes and fees
17319 4BR Townhouse Heated Pool near Disney
A covered swimming pool with a view of a grassy area and trees.

19. 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.
$623 nightly
The price is $692
Nov 3 - Nov 4
Total with taxes and fees
7BR Lakefront | Pool & Hot Tub
An aerial view of a residential area with a large swimming pool complex, surrounded by single-family homes and a body of water.

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

Family 5BR w/ Pool & Grill Near Disney Magic
Kissimmee
$526 nightly
The price is $588
Nov 1 - Nov 2
Total with taxes and fees
Family 5BR w/ Pool & Grill Near Disney Magic
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

Marriott's Grande Vista

Marriott's Grande Vista

10/10 Excellent
"amazing property, huge villas and multiple pools, very good price for what you get"
Olivia Grace 6-night trip
Posted less than an hour ago
Marriott's Grande Vista

Find out more about Windermere

Windermere Villas information

Number of reviews
219
Accommodation
9824 Villas
Lowest Price
$175
Highest Price
$1,053

Frequently asked questions

How much do villas in Windermere cost?
You'll pay between $175 and $1,053 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 9.5. 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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