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Check prices for these dates

Next weekend
17 Oct - 19 Oct
In two weeks
24 Oct - 26 Oct
In one month
7 Nov - 9 Nov
In two months
5 Dec - 7 Dec

Cottages in Windermere

Charming 2-bedroom Country Cottage in Kissimmee with private parking
Exterior

Charming 2-bedroom Country Cottage in Kissimmee with private parking

10.0 out of 10, Exceptional, (3)
"great experience. very clean and in a good area"
The price is SAR 394
SAR 522 total
includes taxes & fees
20 Oct - 21 Oct
Charming 2-bedroom Country Cottage in Kissimmee with private parking
Downtown Cottage
1 bedroom, desk, iron/ironing board, free WiFi

Downtown Cottage

8.4 out of 10, Very Good, (6)
"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 236
SAR 657 total
includes taxes & fees
12 Oct - 13 Oct
Downtown Cottage
Tiny Hidden Cottage
Interior

Tiny Hidden Cottage

9.2 out of 10, Wonderful, (53)
"We had such a great time staying here. A cute little spot made a great quick stay for us."
The price is SAR 296
SAR 575 total
includes taxes & fees
20 Oct - 21 Oct
Tiny Hidden Cottage
Incredible Private Lakefront Cottage Retreat
Exterior

Incredible Private Lakefront Cottage Retreat

10.0 out of 10, Exceptional, (27)
"One of our best stays. "
The price is SAR 503
SAR 1,319 total
includes taxes & fees
18 Oct - 19 Oct
Incredible Private Lakefront Cottage Retreat
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Exterior

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 321
SAR 887 total
includes taxes & fees
13 Oct - 14 Oct
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
Exterior

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema

3.0 star property
The price is SAR 651
SAR 3,192 total
includes taxes & fees
14 Oct - 15 Oct
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
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 300
SAR 820 total
includes taxes & fees
12 Oct - 13 Oct
Hidden Lake View Cottage 5 miles from Disney!
Disney, Universal and Legoland Getaway
Exterior

Disney, Universal and Legoland Getaway

9.2 out of 10, Wonderful, (9)
"I love the place ! It was beautiful! Enough room for everyone "
The price is SAR 281
SAR 810 total
includes taxes & fees
12 Oct - 13 Oct
Disney, Universal and Legoland Getaway
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
Fridge, microwave, oven, stovetop

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

8.6 out of 10, Excellent, (16)
"The AC gave us trouble a few times. Host was great! Had some waters and granola bars there for us which was a nice touch. "
The price is SAR 514
SAR 1,167 total
includes taxes & fees
23 Oct - 24 Oct
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
Jedi cottage 4 miles from Disney! Mins from universal!
Exterior

Jedi cottage 4 miles from Disney! Mins from universal!

9.4 out of 10, Exceptional, (23)
"We loved staying here! "
The price is SAR 281
SAR 810 total
includes taxes & fees
12 Oct - 13 Oct
Jedi cottage 4 miles from Disney! Mins from universal!
Perfect Place for a Perfect Vacation
Exterior

Perfect Place for a Perfect Vacation

3.0 star property
10.0 out of 10, Exceptional, (1)
The price is SAR 351
SAR 787 total
includes taxes & fees
21 Oct - 22 Oct
Perfect Place for a Perfect Vacation
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. "
The price is SAR 428
SAR 999 total
includes taxes & fees
3 Nov - 4 Nov
Charming 2-bedroom cottage in Kissimmee
Tiny house close to Disney KISSIMMEE
2 bedrooms, iron/ironing board, WiFi, bed sheets

Tiny house close to Disney KISSIMMEE

2.0 star property
The price is SAR 210
SAR 590 total
includes taxes & fees
20 Oct - 21 Oct
Tiny house close to Disney KISSIMMEE
161 - 4 bed Gem at Terraverde Resort
House (4 Bedrooms) | Interior

161 - 4 bed Gem at Terraverde Resort

3.0 star property
The price is SAR 449
SAR 1,268 total
includes taxes & fees
24 Oct - 25 Oct
161 - 4 bed Gem at Terraverde Resort
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Exterior

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

10.0 out of 10, Exceptional, (28)
"Absolutely beautiful place, fully equipped and close to everything. We very much enjoyed our stay."
The price is SAR 675
SAR 1,324 total
includes taxes & fees
25 Oct - 26 Oct
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
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

The price is SAR 304
SAR 772 total
includes taxes & fees
15 Oct - 16 Oct
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Family-Friendly Cottage Near Orlando’s Top Attractions
Interior

Family-Friendly Cottage Near Orlando’s Top Attractions

The price is SAR 338
SAR 767 total
includes taxes & fees
20 Oct - 21 Oct
Family-Friendly Cottage Near Orlando’s Top Attractions
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 608
SAR 1,625 total
includes taxes & fees
12 Oct - 13 Oct
Family-friendly Home w/ Lanai ~ 6 Mi to Disney
Charming cottage 10 mins to Disney, Pool, Mini Golf, Fitness room and more!
Exterior

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

The price is SAR 334
SAR 835 total
includes taxes & fees
19 Oct - 20 Oct
Charming cottage 10 mins to Disney, Pool, Mini Golf, Fitness room and more!
Cozy Tropical Cottage - 4 mi to Disney
Terrace/patio

Cozy Tropical Cottage - 4 mi to Disney

The price is SAR 499
SAR 1,058 total
includes taxes & fees
1 Nov - 2 Nov
Cozy Tropical Cottage - 4 mi to Disney
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

Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

10/10 Excellent
"Great"
Melissa 2-night trip
Posted 2 hours ago
Rosen Inn at Pointe Orlando

Frequently asked questions

How much do cottages in Windermere cost?
Rates for cottages in Windermere range between SAR 522 and SAR 3,192 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.

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