A lakeside community with houses and boats.

Villas in Windermere

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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
$494 nightly
The price is $548
Sep 10 - Sep 11
Total with taxes and fees
Rustic Hideaway - Great Location + Pet Friendly!
Interior

2. 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.
$412 nightly
The price is $433
Sep 13 - Sep 14
Total with taxes and fees
3BR Townhouse Right in Front of Epic Universe!
Exterior

3. 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
Pool

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.
$944 nightly
The price is $1,049
Sep 9 - Sep 10
Total with taxes and fees
4,800 sf Estate | Pool, Lake, Weddings and Events
Exterior

5. 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.
$231 nightly
The price is $254
Sep 6 - Sep 7
Total with taxes and fees
Charming Villa near Disney, pool, 4 beds, sleeps 5
Villa (4 Bedrooms) | Interior

6. 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
$291 nightly
The price is $324
Sep 28 - Sep 29
Total with taxes and fees
Contemporary 4BR Townhome With Pool & Themed Rooms
Exterior

7. Amazing Spider | Disney, Slides & River

Amazing Spider | Disney, Slides & River
Kissimmee
$271 nightly
The price is $306
Sep 9 - Sep 10
Total with taxes and fees
Amazing Spider | Disney, Slides & River
Villa (4 Bedrooms) | Interior

8. 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)
$386 nightly
The price is $400
Sep 7 - Sep 8
Total with taxes and fees
Emerald Garden - Resort - 15 Min to Disney - Pets
Exterior

9. 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.
$167 nightly
The price is $185
Sep 13 - Sep 14
Total with taxes and fees
Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
Exterior

10. 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.
Storey Lake Resort~Heated Pool~Brand New~Designer
Exterior

11. 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
Sep 7 - Sep 8
Total with taxes and fees
Cozy 3bd Townhouse | Near Disney| Encantada Resort
Exterior

12. 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
Sep 18 - Sep 19
Total with taxes and fees
Clermont Tiny Home: Main Floor Queen, Lofts & No Pet Fees
Pool

13. Beautiful 7 Bedroom Villa - 4 King Suites, 5.5 Bath, Sleeps 16!

Beautiful 7 Bedroom Villa - 4 King Suites, 5.5 Bath, Sleeps 16!
Kissimmee
8.6 out of 10, Excellent, (90 reviews)
"It was a very nice house my family and I really enjoyed it and made beautiful memories the property manager was very quick to get back with me and helpful, it was very close and convenient to the parks. Would love to stay here again."
United States
Cheryl D.
$831 nightly
The price is $930
Sep 6 - Sep 7
Total with taxes and fees
Beautiful 7 Bedroom Villa - 4 King Suites, 5.5 Bath, Sleeps 16!
Pool

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.
$682 nightly
The price is $757
Sep 28 - Sep 29
Total with taxes and fees
7BR Lakefront | Pool & Hot Tub
Exterior

15. 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
Sep 8 - Sep 9
Total with taxes and fees
Shiny Legendary | Disney, River & Slides
Villa (3 Bedrooms) | Interior

16. Upstay Modern 3BR Townhome With Pool Near Disney

Upstay Modern 3BR Townhome With Pool Near Disney
3.5 star property
Kissimmee
$241 nightly
The price is $273
Sep 14 - Sep 15
Total with taxes and fees
Upstay Modern 3BR Townhome With Pool Near Disney
Interior

17. 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.
$426 nightly
The price is $473
Sep 6 - Sep 7
Total with taxes and fees
At Lakes Upscale Villa/Next to Downtown Orlando
Exterior

18. 4801 ML - Ideal Retreat Townhome Oasis with Pool

4801 ML - Ideal Retreat Townhome Oasis with Pool
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Everything was absolutely perfect and as described in the listing. The host was very nice, made sure our check in process was smooth and we didn’t have any problems throughout the whole stay. Highly recommend this property and it’s very affordable! "
United States
LATONYA S.
$552 nightly
The price is $601
Sep 29 - Sep 30
Total with taxes and fees
4801 ML - Ideal Retreat Townhome Oasis with Pool
Exterior

19. Luxury 6BR Pool Villa! Near Disney-Close to Everything, Spa, 3000ft2!!

Luxury 6BR Pool Villa! Near Disney-Close to Everything, Spa, 3000ft2!!
Kissimmee
9.4 out of 10, Exceptional, (3 reviews)
"great home, pool heating was excellent, community pool was awesome, great stay "
United States
Mario L.
$344 nightly
The price is $385
Sep 28 - Sep 29
Total with taxes and fees
Luxury 6BR Pool Villa! Near Disney-Close to Everything, Spa, 3000ft2!!
Villa, 6 Bedrooms | Exterior

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
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.
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

Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

8/10 Good
"excellent service! the staff was professional, helpful, and knowledgeable."
Wisner 3-night trip
Posted less than an hour ago
Drury Plaza Hotel Orlando - Disney Springs Area

Find out more about Windermere

Windermere Villas information

Number of reviews
259
Accommodation
9822 Villas
Lowest Price
$182
Highest Price
$1,049

Frequently asked questions

How much do villas in Windermere cost?
You'll pay between $182 and $1,049 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 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.

Explore a world of travel with Expedia