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Compare 1223 Cottages in Windermere with updated reviews, rates, and availability.

Orlando Lakefront Tiny House Community
The Club House | Individually decorated, individually furnished, laptop workspace

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (236)
"Beautiful, quiet and peaceful. Lots of local wildlife to observe. Simple check in. Hosts were very accommodating and helpful. Would stay here again in the future"
The price is NT$2,506
NT$5,210 total
includes taxes & fees
Jan 6 - 2025/1/7
Orlando Lakefront Tiny House Community
Up to Scale With Margaritas
Property grounds

Up to Scale With Margaritas

3.0 star property
8.8 out of 10, Excellent, (6)
"The only issue was the upstairs airconditioner was not working in terms the rooms were hot while hallway was cold. But nice for our family. "
Up to Scale With Margaritas
Stunning Lakeview Townhome w/ Private Pool!
Outdoor pool

Stunning Lakeview Townhome w/ Private Pool!

4.0 star property
8.4 out of 10, Very Good, (9)
"Perfect location house was just what is described "
Stunning Lakeview Townhome w/ Private Pool!
8000 Lost Shaker Lane
Interior

8000 Lost Shaker Lane

3.0 star property
9.6 out of 10, Exceptional, (5)
"Lots of room , beautifully decorated. Close to everything we needed for the weekend . "
8000 Lost Shaker Lane
Davenport Family Home ~ 10 Mi to Animal Kingdom
House (3 Bedrooms) | Interior

Davenport Family Home ~ 10 Mi to Animal Kingdom

3.0 star property
10.0 out of 10, Exceptional, (1)
"Perfect two day stay for us … close to everything we n ended it to be. "
Davenport Family Home ~ 10 Mi to Animal Kingdom
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003
Outdoor pool

Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003

3.0 star property
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003
Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621
Pool

Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621

3.0 star property
Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621
Parkside Serenity by Avantstay Private Pool!
Interior

Parkside Serenity by Avantstay Private Pool!

3.0 star property
Parkside Serenity by Avantstay Private Pool!
Elegant + Spacious Kissimmee Vacation Rental Home!
Interior

Elegant + Spacious Kissimmee Vacation Rental Home!

3.0 star property
8.0 out of 10, Very Good, (1)
"Communication on the property was excellent. Comfortable"
Elegant + Spacious Kissimmee Vacation Rental Home!
Townhome Splash Pool BBQ Free Water Park!
Outdoor pool

Townhome Splash Pool BBQ Free Water Park!

3.5 star property
9.6 out of 10, Exceptional, (9)
"Nice and relaxing quiet neighborhood "
Townhome Splash Pool BBQ Free Water Park!
Orlando Home w/ Private Pool: 10 Mi to UCF Campus!
House (3 Bedrooms) | Private kitchen | Paper towels

Orlando Home w/ Private Pool: 10 Mi to UCF Campus!

3.0 star property
Orlando Home w/ Private Pool: 10 Mi to UCF Campus!
16 Mi to Disney: Cottage w/ Deck in Winter Garden
Cottage (1 Bedroom) | Interior

16 Mi to Disney: Cottage w/ Deck in Winter Garden

3.0 star property
10.0 out of 10, Exceptional, (1)
"This house is adorable! It was perfect for us as a couple. Very sweetly decorated and homey. The neighborhood is very quiet and off the beaten path, as they say, yet very close to stores and beautiful downtown Winter Garden. We would SO stay again! Would love to do a seasonal stay. "
16 Mi to Disney: Cottage w/ Deck in Winter Garden
Sunlit Davenport Family Home w/ Lanai & Gas Grill!
House (5 Bedrooms) | Interior

Sunlit Davenport Family Home w/ Lanai & Gas Grill!

3.0 star property
8.0 out of 10, Very Good, (1)
"House nicely kept, lots of room and beds for large gatherings. Clean, convenient washer and dryer in unit, great location, close to shops and restaurants. Overall, really nice place to stay. "
Sunlit Davenport Family Home w/ Lanai & Gas Grill!
3000 Latitude Lane
Interior

3000 Latitude Lane

3.0 star property
10.0 out of 10, Exceptional, (2)
"Great stay!"
3000 Latitude Lane
Lake-view Home w/ Game Room in Orlando!
House (4 Bedrooms) | Interior

Lake-view Home w/ Game Room in Orlando!

3.0 star property
Lake-view Home w/ Game Room in Orlando!
Davenport Home w/ Game Room, Home Theater, Pool
Property grounds

Davenport Home w/ Game Room, Home Theater, Pool

3.0 star property
10.0 out of 10, Exceptional, (1)
"What an amazing home! Clean and everything you need for a staycation or trip to Disney! The pictures online do not do this Gargage justice. It’s an arcade in the home. So much fun! I would recommend this home for all. "
Davenport Home w/ Game Room, Home Theater, Pool
Caribbean Dreamin
Cottage, Multiple Beds, Patio, Garden View | 3 bedrooms, free WiFi, bed sheets

Caribbean Dreamin

3.0 star property
10.0 out of 10, Exceptional, (1)
"This Caribbean Dreamin property is awesome! It is clean, spacious, and very well kept. Contrary to the contract, the house includes all the amenities for all bathrooms as well as dishwashing detergent. Nice touch! The community is very pretty and well kept. Shopping nearby. Unfortunately, we were here for a couple nights during Hurricane Milton so didn't go out at all. But being in a nice home away from home made a difference during the stressful time. I would highly recommend this...
Caribbean Dreamin
Family Home in Davenport w/ Pool ~ 8 Mi to Disney
Interior

Family Home in Davenport w/ Pool ~ 8 Mi to Disney

3.0 star property
Family Home in Davenport w/ Pool ~ 8 Mi to Disney
Star Stay at Championsgate Resort by Shine Villas 023
Villa (Star Stay at Championsgate Resort by ) | Exterior

Star Stay at Championsgate Resort by Shine Villas 023

2.0 star property
10.0 out of 10, Exceptional, (1)
"Excellent communication. Property was immaculate. Management was very easy to deal with and made our stay very comfortable and pleasant."
Star Stay at Championsgate Resort by Shine Villas 023
Magical Themed Villa in Windsor Isalnd
Pool

Magical Themed Villa in Windsor Isalnd

3.0 star property
Magical Themed Villa in Windsor Isalnd
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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Other property types in Windermere

Lake Buena Vista Resort Village & Spa
2 outdoor pools, a heated pool, open 8:00 AM to 10:00 PM, pool umbrellas

Lake Buena Vista Resort Village & Spa

4.0 star property
8.4 out of 10, Very Good, (8221)
"Appliances should be updated. Great room along with Great customer service! Would definitely use again!"
Lake Buena Vista Resort Village & Spa
The View Studio Suites and Event Venue
Property entrance

The View Studio Suites and Event Venue

3.5 star property
8.4 out of 10, Very Good, (645)
"Good breakfast."
The price is NT$2,502
NT$2,814 total
includes taxes & fees
Jan 13 - 2025/1/14
The View Studio Suites and Event Venue
Floridays Resort Orlando
2 outdoor pools, a heated pool, open 7:00 AM to 11:00 PM, pool umbrellas

Floridays Resort Orlando

3.5 star property
8.6 out of 10, Excellent, (11121)
"The front staff was very friendly and informative. Cute little place near a ton of activities. Recommend "
The price is NT$6,151
NT$8,024 total
includes taxes & fees
Jan 6 - 2025/1/7
Floridays Resort Orlando
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.

Frequently asked questions

How much do cottages in Windermere cost?
You can expect to pay between NT$2,506 and NT$2,506 per night for cottages in Windermere. Whatever your budget, an epic stay is a click 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.
Are there any family-friendly cottages in Windermere?
If you want to be close to nature in Windermere, we recommend Fresh And Remodeled In Vista Cay Townhome. With a 3-star rating and handy amenities like an outdoor entertainment area and WiFi, you’ll find it easy to settle in at this family-friendly cottage. Windermere boasts an array of family-friendly attractions to check out when you need to keep the kids busy. Tibet Butler Preserve and Isleworth Golf and Country Club guarantee a fun day out for all ages.
Why book your cottage in Windermere with Expedia?
Booking a cottage in Windermere is as easy as clicking on your travel dates and selecting your ideal place for a vacation in the outdoors. From luxurious retreats to low-cost stays and cottages that offer perks like a hot tub, Expedia has something for all tastes. As for the best deals around? We’ve have them as well!
How can I find cheap cottages in Windermere?
With Expedia’s convenient filter tool, comparing cheap cottages in Windermere couldn’t be easier. To view accommodations that’ll make your bank balance smile, narrow down your search by star rating, budget and amenities.
What is there to do in Windermere near my cottage?
If you want to explore the sights of Windermere, don’t miss Isleworth Golf and Country Club. It’s a winner with tourists and locals alike.