A lakeside community with houses and boats.

Villas in Windermere

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Windermere villas

Exterior

1. New Vista Cay Home | Universal & Convention

New Vista Cay Home | Universal & Convention
Orlando
$174 nightly
The price is $192
Aug 24 - Aug 25
Total with taxes and fees
New Vista Cay Home | Universal & Convention
A heated pool

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)
"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.
$956 nightly
The price is $1,061
Aug 24 - Aug 25
Total with taxes and fees
4,800 sf Estate | Pool, Lake, Weddings and Events
Villa (4 Bedrooms) | Interior

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
$292 nightly
The price is $325
Sep 15 - Sep 16
Total with taxes and fees
Contemporary 4BR Townhome With Pool & Themed Rooms
Exterior

4. 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
Aug 19 - Aug 20
Total with taxes and fees
Shiny Legendary | Disney, River & Slides
Interior

5. 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.
$419 nightly
The price is $440
Sep 13 - Sep 14
Total with taxes and fees
3BR Townhouse Right in Front of Epic Universe!
Exterior

6. 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, (34 reviews)
"Rental was spacious and met all of our needs."
United States
Nikolaus K.
$210 nightly
The price is $235
Aug 20 - Aug 21
Total with taxes and fees
Completely Renovated 3/2 Close to Disney parks
Interior

7. Contemporary Villa next to Disney!

Contemporary Villa next to Disney!
Kissimmee
9.0 out of 10, Wonderful, (22 reviews)
"The Villa was GREAT! Clean, comfortable, quiet"
United States
Glenn H.
$207 nightly
The price is $232
Aug 19 - Aug 20
Total with taxes and fees
Contemporary Villa next to Disney!
Smart TV

8. Beauty 4 miles to Disney 3Br 2Ba Pool Home

Beauty 4 miles to Disney 3Br 2Ba Pool Home
Indian Wells
10.0 out of 10, Exceptional, (5 reviews)
"Spotlessly clean and very quiet. Excellent stay "
United States
Dina A.
$261 nightly
The price is $292
Aug 25 - Aug 26
Total with taxes and fees
Beauty 4 miles to Disney 3Br 2Ba Pool Home
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.
$166 nightly
The price is $184
Aug 19 - Aug 20
Total with taxes and fees
Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
TV

10. Spacious 5-Bedroom Pool Home Near Disney - Private Pool - Game Room

Spacious 5-Bedroom Pool Home Near Disney - Private Pool - Game Room
Clear Creek
$383 nightly
The price is $419
Aug 31 - Sep 1
Total with taxes and fees
Spacious 5-Bedroom Pool Home Near Disney - Private Pool - Game Room
Pool

11. 17319 4BR Townhouse Heated Pool near Disney

17319 4BR Townhouse Heated Pool near Disney
Clermont
$319 nightly
The price is $350
Sep 16 - Sep 17
Total with taxes and fees
17319 4BR Townhouse Heated Pool near Disney
Exterior

12. Amazing Spider | Disney, Slides & River

Amazing Spider | Disney, Slides & River
Kissimmee
$275 nightly
The price is $310
Aug 26 - Aug 27
Total with taxes and fees
Amazing Spider | Disney, Slides & River
Villa (4 Bedrooms) | Interior

13. Upstay: Modern Family Townhome With Pool & Patio

Upstay: Modern Family Townhome With Pool & Patio
3.5 star property
Clermont
$293 nightly
The price is $325
Aug 20 - Aug 21
Total with taxes and fees
Upstay: Modern Family Townhome With Pool & Patio
Exterior

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.
$372 nightly
The price is $416
Aug 30 - Aug 31
Total with taxes and fees
Cozy 3bd Townhouse | Near Disney| Encantada Resort
Exterior

15. 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.
$245 nightly
The price is $269
Aug 19 - Aug 20
Total with taxes and fees
Clermont Tiny Home: Main Floor Queen, Lofts & No Pet Fees
Exterior

16. 3 King Masters + Private Pool | 15 Min Disney

3 King Masters + Private Pool | 15 Min Disney
Kissimmee
9.6 out of 10, Exceptional, (23 reviews)
"Great place for the week while we were in town for volleyball. Clean, great water park areas for the kids. Very spacious and felt very safe in the area "
United States
Heather R.
$598 nightly
The price is $669
Aug 19 - Aug 20
Total with taxes and fees
3 King Masters + Private Pool | 15 Min Disney
Villa, 4 Bedrooms | Exterior

17. Sun Living: Golf Community, Private Pool 809 4 Bedroom Villa

Sun Living: Golf Community, Private Pool 809 4 Bedroom Villa
3.0 star property
Highlands Reserve
8.0 out of 10, Very Good, (1 review)
"Loved the pool. Furniture serviceable not super comfy. Plan to bring in your own toilet paper, dish soap etc, they provide a very minimal amount of everything. "
United States
Michele
$489 nightly
The price is $548
Aug 22 - Aug 23
Total with taxes and fees
Sun Living: Golf Community, Private Pool 809 4 Bedroom Villa
Interior

18. 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, (27 reviews)
"Very nice place and hope to stay there again someday"
United States
Wilbur B.
$471 nightly
The price is $524
Aug 20 - Aug 21
Total with taxes and fees
At Lakes Upscale Villa/Next to Downtown Orlando
Pool

19. 1500R Modern Townhouse Heated Pool Disney Orlando

1500R Modern Townhouse Heated Pool Disney Orlando
Clermont
10.0 out of 10, Exceptional, (2 reviews)
"I enjoyed my stay and the townhouse looks exact to the pictures. The property was clean and well stocked. I’d definitely book again next time I’m in the area. "
United States
Stacey S.
$294 nightly
The price is $322
Sep 16 - Sep 17
Total with taxes and fees
1500R Modern Townhouse Heated Pool Disney Orlando
Exterior

20. 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.
$278 nightly
The price is $307
Aug 19 - Aug 20
Total with taxes and fees
Beach Resort near Disney with Poolside Tike Bar
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 Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"Great resort, friendly staff and lovely pool areas."
Nicholas 17-night trip
Posted less than an hour ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Find out more about Windermere

Windermere Villas information

Number of reviews
138
Accommodation
9823 Villas
Lowest Price
$184
Highest Price
$1,061

Frequently asked questions

How much do villas in Windermere cost?
You'll pay between $184 and $1,061 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 9823 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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