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Check prices for these dates

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

Cottages in Windermere

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

Charming 2-bedroom Country Cottage in Kissimmee with private parking

Kissimmee
9.0 out of 10, Wonderful, (4)
"great experience. very clean and in a good area"
United States
Aubrey V.
Charming 2-bedroom Country Cottage in Kissimmee with private parking
1 bedroom, desk, iron/ironing board, free WiFi
Downtown Cottage

Downtown Cottage

Colonialtown North
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!"
United States
Josh L.
The price is SAR 169
SAR 582 total
includes taxes & fees
3 Dec - 4 Dec
Downtown Cottage
Exterior
Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat

Altamonte Springs
10.0 out of 10, Exceptional, (29)
"One of our best stays. "
United States
matthew m.
The price is SAR 484
SAR 1,264 total
includes taxes & fees
10 Dec - 11 Dec
Incredible Private Lakefront Cottage Retreat
Interior
Tiny Hidden Cottage

Tiny Hidden Cottage

Longwood
9.2 out of 10, Wonderful, (57)
"Check in process and house were both great. "
United States
Marc H.
The price is SAR 267
SAR 542 total
includes taxes & fees
3 Dec - 4 Dec
Tiny Hidden Cottage
The Sunshine Lake Shake | Individually decorated, individually furnished, laptop workspace
Orlando Lakefront Tiny House Community

Orlando Lakefront Tiny House Community

3.0 star property
Orlando
9.4 out of 10, Exceptional, (331)
"We enjoyed our stay."
United States
Ardeeh
The price is SAR 280
SAR 589 total
includes taxes & fees
15 Dec - 16 Dec
Orlando Lakefront Tiny House Community
Fridge, microwave, oven, stovetop
Garden Cottage-Swim/Spa sleeps 6 Ctrl Orlando Disney Universal SeaWorld Beaches,

Garden Cottage-Swim/Spa sleeps 6 Ctrl Orlando Disney Universal SeaWorld Beaches,

Altamonte Springs
8.6 out of 10, Excellent, (17)
"Lots of room to spend time with family and friends. Great location, easy to move around Orlando from here."
United States
Rachael C.
The price is SAR 514
SAR 1,165 total
includes taxes & fees
22 Dec - 23 Dec
Garden Cottage-Swim/Spa sleeps 6 Ctrl Orlando Disney Universal SeaWorld Beaches,
Exterior
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

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

College Park
10.0 out of 10, Exceptional, (29)
"Absolutely beautiful place, fully equipped and close to everything. We very much enjoyed our stay."
United States
Sara R.
The price is SAR 760
SAR 1,405 total
includes taxes & fees
3 Dec - 4 Dec
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Children's area
Charming 2-bedroom cottage in Kissimmee

Charming 2-bedroom cottage in Kissimmee

2.0 star property
Kissimmee
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. "
United States
Gail E.
Charming 2-bedroom cottage in Kissimmee
Exterior
Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation

3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1)
Perfect Place for a Perfect Vacation
Property grounds
Hidden Lake View Cottage 5 miles from Disney!

Hidden Lake View Cottage 5 miles from Disney!

Kissimmee
9.0 out of 10, Wonderful, (2)
"Awesome"
United States
Bulmaro S.
The price is SAR 300
SAR 828 total
includes taxes & fees
3 Dec - 4 Dec
Hidden Lake View Cottage 5 miles from Disney!
Microwave, stovetop
Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE

2.0 star property
Kissimmee
9.0 out of 10, Wonderful, (2)
"The location was great. We really just needed somewhere to sleep because we spent the day at the Disney Parks. The place had enough beds and was a great price."
United States
Christine M.
The price is SAR 263
SAR 650 total
includes taxes & fees
7 Dec - 8 Dec
Tiny house close to Disney KISSIMMEE
Interior
Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions

Kissimmee
10.0 out of 10, Exceptional, (1)
"Perfect location to enjoy Universal Epic and Islands of Adventure with only a 15 minute ride. The beds were very comfortable and the place is clean. We were welcomed with a cute sign, bottled water and cookies. Will definitely stay here again!"
United States
Joyce R.
Family-Friendly Cottage Near Orlando’s Top Attractions
Exterior
Disney, Universal and Legoland Getaway

Disney, Universal and Legoland Getaway

Kissimmee
9.2 out of 10, Wonderful, (9)
"I love the place ! It was beautiful! Enough room for everyone "
United States
Anthony M.
The price is SAR 372
SAR 901 total
includes taxes & fees
2 Jan - 3 January 2026
Disney, Universal and Legoland Getaway
Exterior
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

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

Kissimmee
10.0 out of 10, Exceptional, (2)
"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"
United States
Jennifer b.
The price is SAR 394
SAR 1,081 total
includes taxes & fees
31 Dec - 1 January 2026
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
House (4 Bedrooms) | Interior
Family-friendly Home w/ Lanai ~ 6 Mi to Disney

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

3.0 star property
Montego Bay
Family-friendly Home w/ Lanai ~ 6 Mi to Disney
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

Kissimmee
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Private kitchen
Cozy Lake Cottage - 4 miles to Disney

Cozy Lake Cottage - 4 miles to Disney

Kissimmee
Cozy Lake Cottage - 4 miles to Disney
Exterior
Charming 1-bedroom cottage in Kissimmee

Charming 1-bedroom cottage in Kissimmee

Kissimmee
Charming 1-bedroom cottage in Kissimmee
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

Universal's Endless Summer Resort - Dockside Inn and Suites

Universal's Endless Summer Resort - Dockside Inn and Suites

10/10 Excellent
"Transport to parks was great"
Sara 5-night trip
Posted 1 day ago
Universal's Endless Summer Resort - Dockside Inn and Suites

Frequently asked questions

How much do cottages in Windermere cost?
Rates for cottages in Windermere range between SAR 542 and SAR 2,006 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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