Search Windermere Cottage Rentals from CA $90

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Browse Select Windermere Cottages

Our top choices for Windermere cottages

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 CA $131
CA $177 total
includes taxes & fees
Sep 8 - Sep 9
Charming 2-bedroom Country Cottage in Kissimmee with private parking
Orlando Lakefront Tiny House Community
The Club House

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (328)
"We enjoyed our stay."
The price is CA $105
CA $219 total
includes taxes & fees
Aug 25 - Aug 26
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 CA $68
CA $221 total
includes taxes & fees
Aug 20 - Aug 21
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 CA $98
CA $199 total
includes taxes & fees
Aug 22 - Aug 23
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 CA $137
CA $408 total
includes taxes & fees
Aug 21 - Aug 22
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 CA $189
CA $455 total
includes taxes & fees
Sep 11 - Sep 12
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 CA $247
CA $489 total
includes taxes & fees
Sep 1 - Sep 2
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. "
The price is CA $111
CA $308 total
includes taxes & fees
Aug 27 - Aug 28
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! "
The price is CA $90
CA $280 total
includes taxes & fees
Aug 20 - Aug 21
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 CA $117
CA $294 total
includes taxes & fees
Aug 20 - Aug 21
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 CA $104
CA $298 total
includes taxes & fees
Aug 23 - Aug 24
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 CA $104
CA $298 total
includes taxes & fees
Aug 23 - Aug 24
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 CA $195
CA $564 total
includes taxes & fees
Aug 20 - Aug 21
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 CA $111
CA $316 total
includes taxes & fees
Aug 28 - Aug 29
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
161 - 4 bed Gem at Terraverde Resort
Interior

161 - 4 bed Gem at Terraverde Resort

The price is CA $389
CA $727 total
includes taxes & fees
Aug 24 - Aug 25
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 CA $134
CA $290 total
includes taxes & fees
Aug 26 - Aug 27
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

The price is CA $78
CA $242 total
includes taxes & fees
Aug 26 - Aug 27
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 CA $123
CA $306 total
includes taxes & fees
Aug 21 - Aug 22
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

The price is CA $124
CA $280 total
includes taxes & fees
Aug 20 - Aug 21
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

The price is CA $93
CA $209 total
includes taxes & fees
Aug 21 - Aug 22
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windermere Hotel Reviews

CoCo Key Hotel and Water Resort 

CoCo Key Hotel and Water Resort 

10/10 Excellent
"All the services was excellent "
Sarai 4-night trip
Posted 5 hours ago
CoCo Key Hotel and Water Resort