A lakeside community with houses and boats.

Villas in Windermere

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Windermere villas

1. Rustic Hideaway - Great Location + Pet Friendly!

Rustic Hideaway - Great Location + Pet Friendly!
3.0 star property
Windermere
$505 nightly
The price is $560
Aug 31 - Sep 1
Total with taxes and fees
Rustic Hideaway - Great Location + Pet Friendly!

2. 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)
"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.
$235 nightly
The price is $258
Aug 31 - Sep 1
Total with taxes and fees
Charming Villa near Disney, pool, 4 beds, sleeps 5
A modern multi-story residential building with a symmetrical facade, stone accents, and a central entrance.

3. 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
$290 nightly
The price is $322
Aug 31 - Sep 1
Total with taxes and fees
Contemporary 4BR Townhome With Pool & Themed Rooms
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)
"This property is absolutely beautiful with a ton of space to hang out, relax and have fun! You won't find another place with this many options! "
United States
Hidden Gem C.
$980 nightly
The price is $1,087
Sep 8 - Sep 9
Total with taxes and fees
4,800 sf Estate | Pool, Lake, Weddings and Events
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.
$164 nightly
The price is $182
Sep 27 - Sep 28
Total with taxes and fees
SAFE QUIET PRIVATE Villa - Mins to ORL/Winter Park/Eola FREE PARKING/EV Charging
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.
$420 nightly
The price is $441
Sep 3 - Sep 4
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.

7. Amazing Spider | Disney, Slides & River

Amazing Spider | Disney, Slides & River
Kissimmee
$275 nightly
The price is $310
Aug 31 - Sep 1
Total with taxes and fees
Amazing Spider | Disney, Slides & River
A two-story building with a white picket fence, a staircase, and a clear sky.

8. 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, (35 reviews)
"Rental was spacious and met all of our needs."
United States
Nikolaus K.
$214 nightly
The price is $239
Aug 31 - Sep 1
Total with taxes and fees
Completely Renovated 3/2 Close to Disney parks

9. 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 $413
Aug 31 - Sep 1
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.

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.
$397 nightly
The price is $443
Aug 31 - Sep 1
Total with taxes and fees
Cozy 3bd Townhouse | Near Disney| Encantada Resort
The exterior of Altamonte Mall with a large green sign, palm trees, and a curved entrance.

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

Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
Altamonte Springs
9.2 out of 10, Wonderful, (7 reviews)
"It had everything we needed, and more. It was very pet-friendly. The host was very polite and discreet. Clean and neat. The location cannot be more centric for shops and so on. And, it is a bargain. We wanted to stay lomger, but it was already booked!"
United States
Maria M.
$166 nightly
The price is $184
Aug 31 - Sep 1
Total with taxes and fees
Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
An aerial view of a resort with multiple swimming pools, a water slide, and a tower structure.

12. 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.
$275 nightly
The price is $310
Sep 8 - Sep 9
Total with taxes and fees
Shiny Legendary | Disney, River & Slides
A modern building with a white exterior, stone accents, and a small garden with palm trees.

13. Upstay: Modern Family Townhome With Pool & Patio

Upstay: Modern Family Townhome With Pool & Patio
3.5 star property
Clermont
$294 nightly
The price is $326
Sep 14 - Sep 15
Total with taxes and fees
Upstay: Modern Family Townhome With Pool & Patio
A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with two chairs.

14. Family Friendly Villa near Disney, pool, sleeps 5

Family Friendly Villa near Disney, pool, sleeps 5
Vacation Village
9.0 out of 10, Wonderful, (2 reviews)
"It was clean. "
United States
Amy E.
$205 nightly
The price is $225
Sep 6 - Sep 7
Total with taxes and fees
Family Friendly Villa near Disney, pool, sleeps 5
A residential complex with multiple houses, a parking area, and a swimming pool.

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

Storey Lake Resort~Heated Pool~Brand New~Designer
Kissimmee
10.0 out of 10, Exceptional, (6 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.
$450 nightly
The price is $473
Sep 3 - Sep 4
Total with taxes and fees
Storey Lake Resort~Heated Pool~Brand New~Designer
A modern kitchen with a bar area, a dining space, and a living area with a fireplace.

16. 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, (28 reviews)
"Very nice place and hope to stay there again someday"
United States
Wilbur B.
$463 nightly
The price is $514
Sep 6 - Sep 7
Total with taxes and fees
At Lakes Upscale Villa/Next to Downtown Orlando
A covered swimming pool with a view of a grassy area and trees.

17. 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.
$635 nightly
The price is $704
Sep 28 - Sep 29
Total with taxes and fees
7BR Lakefront | Pool & Hot Tub
A building with a 'General Store' and 'Pro Shop' sign, a parking lot, and a white fence.

18. Clermont Tiny Home: Main Floor Queen, Lofts & No Pet Fees

Clermont Tiny Home: Main Floor Queen, Lofts & No Pet Fees
Clermont
10.0 out of 10, Exceptional, (19 reviews)
"This was our second time staying here. It was clean and well stocked for the week. The pools at the place were great. We were able to enjoy pickleball and golf on the resort as well. "
United States
Carolyn B.
$254 nightly
The price is $278
Aug 31 - Sep 1
Total with taxes and fees
Clermont Tiny Home: Main Floor Queen, Lofts & No Pet Fees

19. Luxurious Brand New 8 Bed 6 Bath Disney Theme Villa With Free Heated Pool & BBQ

Luxurious Brand New 8 Bed 6 Bath Disney Theme Villa With Free Heated Pool & BBQ
Clermont
9.8 out of 10, Exceptional, (21 reviews)
"This place was absolutely wonderful for our family trip. We were so pleased with how nice and clean the house was upon arrival. The decor created a truly cozy and inviting atmosphere, making us feel right at home. The host was exceptionally helpful throughout our stay. We would highly recommend this property to anyone looking for a comfortable and pleasant getaway."
United States
Alia J.
$1,055 nightly
The price is $1,157
Sep 1 - Sep 2
Total with taxes and fees
Luxurious Brand New 8 Bed 6 Bath Disney Theme Villa With Free Heated Pool & BBQ
A resort with multiple swimming pools, a dock, and a residential area with houses.

20. Stars Align @ Storey Lake By Shine Villas 6 Bedroom Villa

Stars Align @ Storey Lake By Shine Villas 6 Bedroom Villa
3.0 star property
Kissimmee
$672 nightly
The price is $763
Aug 31 - Sep 1
Total with taxes and fees
Stars Align @ Storey Lake By Shine Villas 6 Bedroom Villa
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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Great for family. Big apartment"
Shavit 3-night trip
Posted 1 hour ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Find out more about Windermere

Windermere Villas information

Number of reviews
221
Accommodation
9822 Villas
Lowest Price
$182
Highest Price
$1,157

Frequently asked questions

How much do villas in Windermere cost?
You'll pay between $182 and $1,157 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 9.8. 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 9822 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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