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Browse Select Windermere Cottages

Our top choices for Windermere cottages

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

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

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

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

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,

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!

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

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!

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

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

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!

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

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

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

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

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

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!

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

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

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.
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Top Windermere Hotel Reviews