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Check prices for these dates

In two weeks
5 Sep - 7 Sep
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Cottages in Windermere

Charming 2-bedroom Country Cottage in Kissimmee with private parking
Fridge, microwave, oven, stovetop

Charming 2-bedroom Country Cottage in Kissimmee with private parking

10.0 out of 10, Exceptional, (2)
"The house was exactly as shown. It was very clean and really nice. Great space for parking my large trailer. The neighborhood was nice and very quiet. We would definitely stay again."
The price is SAR 394
SAR 522 total
includes taxes & fees
27 Aug - 28 Aug
Charming 2-bedroom Country Cottage in Kissimmee with private parking
Orlando Lakefront Tiny House Community
The Club House | 2 bedrooms, individually decorated, individually furnished

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (328)
"We enjoyed our stay."
The price is SAR 286
SAR 596 total
includes taxes & fees
25 Aug - 26 Aug
Orlando Lakefront Tiny House Community
Downtown Cottage
1 bedroom, desk, iron/ironing board, free WiFi

Downtown Cottage

9.6 out of 10, Exceptional, (4)
"Thank you for a wonderful stay. This gem of a guest house is in a perfect location in the Mills50 area of downtown Orlando. A perfectly cozy little home with comfortable beds and a welcoming environment. We look forward to staying again next time we are in Orlando!"
The price is SAR 169
SAR 582 total
includes taxes & fees
21 Aug - 22 Aug
Downtown Cottage
Tiny Hidden Cottage
Interior

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (49)
"Great location, quiet area & friendly hosts. Could use some updated kitchenware and pans, toaster didnt seem to work. Otherwise was a nice place."
The price is SAR 267
SAR 542 total
includes taxes & fees
21 Aug - 22 Aug
Tiny Hidden Cottage
Incredible Private Lakefront Cottage Retreat
Property grounds

Incredible Private Lakefront Cottage Retreat

10.0 out of 10, Exceptional, (27)
"One of our best stays. "
The price is SAR 372
SAR 1,110 total
includes taxes & fees
21 Aug - 22 Aug
Incredible Private Lakefront Cottage Retreat
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
Property grounds

Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,

8.4 out of 10, Very Good, (15)
"This was a cute place in a nice neighborhood "
The price is SAR 514
SAR 1,236 total
includes taxes & fees
11 Sep - 12 Sep
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
2 bedrooms, in-room safe, desk, iron/ironing board

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

10.0 out of 10, Exceptional, (26)
"Easy and convenient in a nice place "
The price is SAR 672
SAR 1,328 total
includes taxes & fees
1 Sep - 2 Sep
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Charming 2-bedroom cottage in Kissimmee
Children's area

Charming 2-bedroom cottage in Kissimmee

2.0 star property
10.0 out of 10, Exceptional, (1)
"Kudos to the hosts. A seamless experience. My first ever vacation rental and I was very impressed. The cottage was super clean and was equipped with everything and then some. "
Charming 2-bedroom cottage in Kissimmee
Jedi cottage 4 miles from Disney! Mins from universal!
Fridge, microwave, oven, stovetop

Jedi cottage 4 miles from Disney! Mins from universal!

9.4 out of 10, Exceptional, (21)
"We loved staying here! "
Jedi cottage 4 miles from Disney! Mins from universal!
Beautiful, family-friendly cottage just 4 miles from Disney World
Fridge, microwave, oven, stovetop

Beautiful, family-friendly cottage just 4 miles from Disney World

9.4 out of 10, Exceptional, (11)
"Perfect for our stay in Orlando/Kissimmee. Close to everything we were attending, quiet, clean, and well supplied with the basics."
The price is SAR 338
SAR 820 total
includes taxes & fees
20 Sep - 21 Sep
Beautiful, family-friendly cottage just 4 miles from Disney World
Disney, Universal and Legoland Getaway
A heated pool

Disney, Universal and Legoland Getaway

9.2 out of 10, Wonderful, (9)
The price is SAR 281
SAR 810 total
includes taxes & fees
23 Aug - 24 Aug
Disney, Universal and Legoland Getaway
Hidden Lake View Cottage 5 miles from Disney!
Property grounds

Hidden Lake View Cottage 5 miles from Disney!

9.0 out of 10, Wonderful, (2)
"Awesome"
The price is SAR 281
SAR 810 total
includes taxes & fees
23 Aug - 24 Aug
Hidden Lake View Cottage 5 miles from Disney!
Family-friendly Home w/ Lanai ~ 6 Mi to Disney
House (4 Bedrooms) | Interior

Family-friendly Home w/ Lanai ~ 6 Mi to Disney

3.0 star property
The price is SAR 529
SAR 1,533 total
includes taxes & fees
21 Aug - 22 Aug
Family-friendly Home w/ Lanai ~ 6 Mi to Disney
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Outdoor pool, a heated pool

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

10.0 out of 10, Exceptional, (2)
"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"
The price is SAR 409
SAR 961 total
includes taxes & fees
20 Sep - 21 Sep
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
161 - 4 bed Gem at Terraverde Resort
House (4 Bedrooms) | Interior

161 - 4 bed Gem at Terraverde Resort

The price is SAR 1,063
SAR 1,984 total
includes taxes & fees
3 Sep - 4 Sep
161 - 4 bed Gem at Terraverde Resort
Perfect Place for a Perfect Vacation
Outdoor dining

Perfect Place for a Perfect Vacation

3.0 star property
The price is SAR 365
SAR 787 total
includes taxes & fees
25 Aug - 26 Aug
Perfect Place for a Perfect Vacation
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Property grounds

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Charming cottage 10 mins to Disney, Pool, Mini Golf, Fitness room and more!
Dining

Charming cottage 10 mins to Disney, Pool, Mini Golf, Fitness room and more!

The price is SAR 409
SAR 901 total
includes taxes & fees
20 Sep - 21 Sep
Charming cottage 10 mins to Disney, Pool, Mini Golf, Fitness room and more!
Family-Friendly Cottage Near Orlando’s Top Attractions
Interior

Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Smart TV, fireplace

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD

4.0 out of 10, (1)
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
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

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent
"It was a wonderful stay the breakfast was great witj lots of opetions. Staff was kind. There is a targer walking distance which was great super close to disney world but a drive to univeral or other attractions. "
Alisa 7-night trip
Posted 6 hours ago
Home2 Suites by Hilton Orlando at Flamingo Crossings

Frequently asked questions

How much do cottages in Windermere cost?
Rates for cottages in Windermere range between SAR 267 and SAR 514 per night. Whatever your budget, you'll find an ideal place to get reacquainted with nature. 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?
Reserving a cottage in Windermere is as simple as working out your travel dates and selecting your ideal place for outdoor recreation and relaxation. From luxurious retreats to low-cost stays and cottages that have amenities like laundry facilities, Expedia has something for all traveler styles. As for awesome deals? We've got them as well!
How can I find cheap cottages in Windermere?
Expedia is here to help you locate cheap cottages in Windermere. To reserve your perfect stay in a couple of quick clicks, try out the filter tool to refine your search by star rating, budget and amenities.