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Compare 1516 Cottages in Windermere with updated reviews, rates, and availability.

Orlando Lakefront Tiny House Community
Exterior

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 AED 279
AED 582 total
includes taxes & fees
6 Jan - 7 January 2025
Orlando Lakefront Tiny House Community
Tiny Hidden Cottage
Room

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (24)
"The house was perfect for my weekend stay and I hope to stay again on my next trip"
The price is AED 290
AED 563 total
includes taxes & fees
25 Dec - 26 Dec
Tiny Hidden Cottage
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Orlando oasis ☀️

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

9.8 out of 10, Exceptional, (9)
"It's a lovely, well-appointed, well-located place. The cottage is within easy walking distance of multiple restaurants. The communication was excellent. I hope to stay at the cottage again soon!"
The price is AED 643
AED 1,250 total
includes taxes & fees
14 Jan - 15 January 2025
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Gorgeous Cottage near Lake Louisa & mins 2 Disney.
Private kitchen

Gorgeous Cottage near Lake Louisa & mins 2 Disney.

9.6 out of 10, Exceptional, (37)
"Glad to report place is as nice as depicted in photos. House is part of a duplex in a community of homes called Vacation Village Resort. Two true bedrooms and two true baths. I don't want to give away the surprise but have a couple of quarters handy especially if traveling with kids. Small but highly functional kitchen area with full size refrigerator and a dishwasher as well. "
Gorgeous Cottage near Lake Louisa & mins 2 Disney.
Enchanted Cottage with Pool and Mini-Golf Near Disney
Enchanted Cottage - 1 bedroom, 1 bathroom near Disney

Enchanted Cottage with Pool and Mini-Golf Near Disney

9.6 out of 10, Exceptional, (14)
"This location was perfect for me and my two dogs. "
Enchanted Cottage with Pool and Mini-Golf Near Disney
Frankly Fintastic - Happy Days in Margaritaville! Min to Resorts, Pet Friendly
Unwind in the private hot tub, soaking away your cares in the sunshine

Frankly Fintastic - Happy Days in Margaritaville! Min to Resorts, Pet Friendly

10.0 out of 10, Exceptional, (3)
"SO nice that each couple had a queen or king sized bed and each bedroom had its own bathroom. Hot tub was a huge bonus after long days on your feet at the theme parks. Very nice house in a beautiful area convenient to the Disney parks."
Frankly Fintastic - Happy Days in Margaritaville! Min to Resorts, Pet Friendly
Up to Scale With Margaritas
Exterior

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!
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!
Cozy Lake Front Cottage
Living area

Cozy Lake Front Cottage

10.0 out of 10, Exceptional, (9)
"Will definitely be staying again"
The price is AED 657
AED 1,168 total
includes taxes & fees
27 Dec - 28 Dec
Cozy Lake Front Cottage
8000 Lost Shaker Lane
Outdoor spa tub

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
Living area

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
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
Living room

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!
Pool

Parkside Serenity by Avantstay Private Pool!

3.0 star property
Parkside Serenity by Avantstay Private Pool!
NEW LISTING! Relaxing 4BR Hideaway in Groveland by RedAwning
Grass,Architecture,Building,House,Lawn

NEW LISTING! Relaxing 4BR Hideaway in Groveland by RedAwning

2.0 star property
The price is AED 524
AED 1,594 total
includes taxes & fees
13 Jan - 14 January 2025
NEW LISTING! Relaxing 4BR Hideaway in Groveland by RedAwning
1-bedroom cottage just a 13-minute walk to Old Town
Exterior of cottage

1-bedroom cottage just a 13-minute walk to Old Town

9.2 out of 10, Wonderful, (122)
"Ideal location for central Fl the parks Well kept grounds and lots of other units of similar type "
1-bedroom cottage just a 13-minute walk to Old Town
4 miles from Disney 5 Star RV Resort! Location Location !The Hidden Gem Cottage!
Outdoor sitting area with water fountain.

4 miles from Disney 5 Star RV Resort! Location Location !The Hidden Gem Cottage!

10.0 out of 10, Exceptional, (21)
"My friend and I came down to FL for the AKC agility invitationals. I was competing with my dog and she drove her down and tagged along at the event. We really didn't stay in the place much, but it was beautiful there! Very Quiet. Ivonne was great, checking in on us and making sure we had everything we needed. Would definitely stay again. "
4 miles from Disney 5 Star RV Resort! Location Location !The Hidden Gem Cottage!
Elegant + Spacious Kissimmee Vacation Rental Home!
Private kitchen

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!
6 Br / 4,5 Bath + Pool/Spa + Game Room / Less than 4 miles from Disney
Pool

6 Br / 4,5 Bath + Pool/Spa + Game Room / Less than 4 miles from Disney

9.6 out of 10, Exceptional, (7)
"Excellent property for a Florida holiday base. Will be staying again in the future"
6 Br / 4,5 Bath + Pool/Spa + Game Room / Less than 4 miles from Disney
Townhome Splash Pool BBQ Free Water Park!
Property grounds

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!
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
Outdoor pool

Lake Buena Vista Resort Village & Spa

4.0 star property
8.4 out of 10, Very Good, (8221)
"I really want to give 5 stars but the when you walk off the elevator to go to the apartment there is an overwhelming musty smell. Then when we were in our apartment the smell was so bad, we got there at 3:30am and I had been driving over 12 hours so at that point I just wanted to sleep and worry about it tomorrow. We bought airfresher the next day, it’s not like we planned to be in the room often, and decided to just deal with it. The couch and the dining chairs really need to be replaced. ...
The price is AED 918
AED 1,141 total
includes taxes & fees
25 Dec - 26 Dec
Lake Buena Vista Resort Village & Spa
The View Studio Suites and Event Venue
Front of property

The View Studio Suites and Event Venue

3.5 star property
8.4 out of 10, Very Good, (644)
"Good breakfast."
The price is AED 281
AED 316 total
includes taxes & fees
12 Jan - 13 January 2025
The View Studio Suites and Event Venue
Floridays Resort Orlando
Outdoor pool

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 AED 691
AED 901 total
includes taxes & fees
6 Jan - 7 January 2025
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 AED 279 and AED 657 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.
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?
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