Villas in Windermere

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Villas in Windermere

Exterior
Last Minute Disney Getaway! Private patio & Themed Bedrooms. Book Now! #115909

Villa in Orlando

$434 nightly
The price is $482
Dec 16 - Dec 17
Total with taxes and fees
Last Minute Disney Getaway! Private patio & Themed Bedrooms. Book Now! #115909
Exterior
Last Minute Disney Getaway! Luxury Villa with Private patio. Book Now! #115911

Villa in Orlando

$558 nightly
The price is $620
Dec 10 - Dec 11
Total with taxes and fees
Last Minute Disney Getaway! Luxury Villa with Private patio. Book Now! #115911
Outdoor dining
Banana Leaf Villa- Book your gathering today!

Villa in Orlovista

2.0 star property
8.0 out of 10, Very Good, (3)
"The management team was superb. She was very helpful and even went above me expectations."
United States
Carleen
$100 nightly
The price is $105
Dec 8 - Dec 9
Total with taxes and fees
Banana Leaf Villa- Book your gathering today!
Exterior
Completely Renovated 3/2 Close to Disney parks

Villa in Royal Palm Bay

10.0 out of 10, Exceptional, (21)
"A perfect accommodation experience. I would like to come again if possible."
China
??
$210 nightly
The price is $235
Dec 7 - Dec 8
Total with taxes and fees
Completely Renovated 3/2 Close to Disney parks
Outdoor dining
Enchanted Villa with Lake View 6-Bedroom in Resort 9 miles to Disney World 15 mi

Villa in Lake Berkley

10.0 out of 10, Exceptional, (2)
"Me and my girls had a blast staying here the home was incredibly beautiful and slept all of just very comfortably! the host was attentive and replied fast with questions. The gate was a little tricky just because we had multiple cars but overall it was a great place!"
United States
Ireland C.
$410 nightly
The price is $460
Dec 8 - Dec 9
Total with taxes and fees
Enchanted Villa with Lake View 6-Bedroom in Resort 9 miles to Disney World 15 mi
Interior
Modern 3 Bed Villa, Newly Renovated, Prime Location

Villa in Kissimmee

3.0 star property
$262 nightly
The price is $275
Dec 9 - Dec 10
Total with taxes and fees
Modern 3 Bed Villa, Newly Renovated, Prime Location
Pool
5BR Heated Pool & Grill w/ Pool Table & Darts!

Villa in Sandy Ridge

10.0 out of 10, Exceptional, (3)
"Wonderful group to work with. Enjoyed a much needed vacation. Host was very easy to get in contact with and solved any issues in a timely manner! Plan on staying again sometime in the future!"
United States
Stacy C.
$364 nightly
The price is $388
Dec 7 - Dec 8
Total with taxes and fees
5BR Heated Pool & Grill w/ Pool Table & Darts!
A heated pool
Spacious Luxurious 6 Bedroom 5 Bath Villa Sleeps 12 Pool, Jacuzzi, near Disney

Villa in Trafalgar Village

8.8 out of 10, Excellent, (9)
"House was big enough for the whole family nice pool great area "
United States
Chrystal S.
$438 nightly
The price is $490
Jan 5 - Jan 6, 2026
Total with taxes and fees
Spacious Luxurious 6 Bedroom 5 Bath Villa Sleeps 12 Pool, Jacuzzi, near Disney
Exterior
Private Heated Pool~Game Loft ~Arcade~Near Disney

Villa in Solterra Resort

10.0 out of 10, Exceptional, (6)
"This was a great place for our family to stay during our trip to Orlando. Derek was very responsive to our messages, and promptly took care of any issues we had during our stay. The beds were comfortable, it was well stocked with everything you’d need to make your stay comfortable, and it was clean and well maintained. I’d definitely bring my family back to stay here again and would recommend “Squeeze the Day” to anyone visiting Orlando. Thanks Derek & Lauren for making our stay great! "
United States
Brent T.
$465 nightly
The price is $470
Dec 17 - Dec 18
Total with taxes and fees
Private Heated Pool~Game Loft ~Arcade~Near Disney
Outdoor pool, a heated pool
🌿Welcome to the Jungle🌿

Villa in Loughman

9.0 out of 10, Wonderful, (16)
"As advertised, safe and quiet neighborhood, the house was wonderful and the grandkids had a great time in pool and jacuzzi."
United States
Teresa W.
$388 nightly
The price is $430
Dec 7 - Dec 8
Total with taxes and fees
🌿Welcome to the Jungle🌿
Exterior
Windsor Hills Resort/3Bedrm/Private Pool/Near Disney

Villa in Windsor Hills

10.0 out of 10, Exceptional, (22)
"Loved this place clean and welcoming"
United States
Marlene K.
$428 nightly
The price is $464
Dec 7 - Dec 8
Total with taxes and fees
Windsor Hills Resort/3Bedrm/Private Pool/Near Disney
Interior
Upstay: Modern Solara Retreat w/ Pool & Games Room

Villa in Kissimmee

3.0 star property
$322 nightly
The price is $365
Dec 8 - Dec 9
Total with taxes and fees
Upstay: Modern Solara Retreat w/ Pool & Games Room
Exterior
Pet Friendly, Modern Tiny Home in Vibrant Clermont!

Villa in Clermont

10.0 out of 10, Exceptional, (13)
"Very cool place, extremely neat and clean and much more comfortable than an RV."
United States
brian d.
$264 nightly
The price is $290
Dec 6 - Dec 7
Total with taxes and fees
Pet Friendly, Modern Tiny Home in Vibrant Clermont!
Outdoor pool, a heated pool, sun loungers
Splendid Lake View Villa With Heated Pool/spa Near Disney

Villa in Loughman

9.2 out of 10, Wonderful, (39)
"Our stay was great. The home is beautiful. Claire was very responsive to our questions. I definitely would stay again. I highly recommend. "
United States
Alfredo V.
$453 nightly
The price is $501
Dec 7 - Dec 8
Total with taxes and fees
Splendid Lake View Villa With Heated Pool/spa Near Disney
Exterior
Kid-Friendly, themed vacation home close to Disney/Universal

Villa in Kissimmee

10.0 out of 10, Exceptional, (4)
"Perfect place to stay very clean had everything we needed. "
United States
Marlo S.
$315 nightly
The price is $353
Dec 13 - Dec 14
Total with taxes and fees
Kid-Friendly, themed vacation home close to Disney/Universal
Villa | 4 bedrooms
New 4BR Villa Themed Beds Magic

Villa in Davenport

2.0 star property
10.0 out of 10, Exceptional, (1)
"The house was immaculate and the owners were very responsive to any needs we had."
United States
Kirsten
$442 nightly
The price is $502
Dec 15 - Dec 16
Total with taxes and fees
New 4BR Villa Themed Beds Magic
Pool
2933 Fable Street · Storey Lake•9BR•Fire Pit•Pool•Hot Tub•Game•EV

Villa in Kissimmee

10.0 out of 10, Exceptional, (14)
"Great accomodations"
United States
David H.
$634 nightly
The price is $634
Dec 7 - Dec 8
Total with taxes and fees
2933 Fable Street · Storey Lake•9BR•Fire Pit•Pool•Hot Tub•Game•EV
Exterior
Lux 6BRVilla w/ Pool&ResortAmenities -10m to Parks

Villa in Kissimmee

2.5 star property
10.0 out of 10, Exceptional, (2)
"We had a fantastic stay at Franks place. Its absolutely perfect for familys. A really spacious property with everything you need to make it a comfortable stay. Really clean and tidy with lots of towels. The beach towels ready to be used were a great addition.Perfectly located, extremely close to Disney and the 192 which has lots of restaurants, giftshops and supermarkets. We would all 100% stay here again."
United Kingdom
Kris S.
$508 nightly
The price is $568
Dec 13 - Dec 14
Total with taxes and fees
Lux 6BRVilla w/ Pool&ResortAmenities -10m to Parks
Exterior
Galactic 7-Bedroom Villa 3 Miles to Disney Star Wars Galaxy Edge

Villa in Kissimmee

10.0 out of 10, Exceptional, (1)
"It was amazingly themed and the host kept up the theme in her communication. We only stayed one night and it was a great time. "
United States
Alyssa J.
$466 nightly
The price is $523
Dec 15 - Dec 16
Total with taxes and fees
Galactic 7-Bedroom Villa 3 Miles to Disney Star Wars Galaxy Edge
Exterior
Pelican by Migration Travel

Villa in Davenport

10.0 out of 10, Exceptional, (5)
"Everything was excellentGreat experience The house was very cleanBenjamin and Kimberly are great hostsLooking forward to staying there again"
Mexico
Ronit M.
$391 nightly
The price is $433
Dec 14 - Dec 15
Total with taxes and fees
Pelican by Migration Travel
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

Lake Buena Vista Resort Village & Spa

Lake Buena Vista Resort Village & Spa

10/10 Excellent
"Great location! Accessibly to all of the parks, shopping, restaurants local culture. Highly recommended…we will be back soon!"
Rosalyn 5-night trip
Posted 2 days ago
Lake Buena Vista Resort Village & Spa

Find out more about Windermere

Windermere Villas information

Number of reviews
138
Accommodation
10207 Villas
Lowest Price
$105
Highest Price
$634

Frequently asked questions

How much do villas in Windermere cost?
You'll pay between $105 and $634 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 10207 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