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Check prices for these dates

In two weeks
Feb 20 - Feb 22
In two months
Apr 3 - Apr 5
In three months
May 1 - May 3
In four months
May 29 - May 31

Our top choices for Windermere cottages

Property grounds

Shore Steps Cottage - Walking Distance To The Town Of Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere
Windermere
$295 nightly
The price is $327
Feb 9 - Feb 10
Total with taxes and fees
Shore Steps Cottage - Walking Distance To The Town Of Windermere
Interior

Downtown Cottage

Downtown Cottage
Colonialtown North
8.6 out of 10, Excellent, (8 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
$158 nightly
The price is $175
Feb 12 - Feb 13
Total with taxes and fees
Downtown Cottage
Iron/ironing board, internet, bed sheets

Quiet Lakefront Retreat near Downtown with Private Patio

Quiet Lakefront Retreat near Downtown with Private Patio
Orlando
$195 nightly
The price is $217
Feb 10 - Feb 11
Total with taxes and fees
Quiet Lakefront Retreat near Downtown with Private Patio
Microwave, stovetop

Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.6 out of 10, Excellent, (4 reviews)
"Just needed a place to stay close to Disney for the night and the place was clean and easy to check in and out. "
United States
Jena B.
$166 nightly
The price is $186
Feb 13 - Feb 14
Total with taxes and fees
Tiny house close to Disney KISSIMMEE
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
9.8 out of 10, Exceptional, (32 reviews)
"Absolutely beautiful place, fully equipped and close to everything. We very much enjoyed our stay."
United States
Sara R.
$332 nightly
The price is $369
Feb 19 - Feb 20
Total with taxes and fees
The Coach House- Entire Home - 2 bedroom/3 bath Orlando 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 reviews)
"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"
United States
Jennifer b.
$241 nightly
The price is $270
Feb 26 - Feb 27
Total with taxes and fees
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Dining

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
$198 nightly
The price is $221
Feb 9 - Feb 10
Total with taxes and fees
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Interior

201-4-hb-beautiful Home at Terraverde

201-4-hb-beautiful Home at Terraverde
2.5 star property
Kissimmee
$2,553 nightly
The price is $2,898
Feb 12 - Feb 13
Total with taxes and fees
201-4-hb-beautiful Home at Terraverde
House (4 Bedrooms) | Interior

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
3.0 star property
Indian Ridge
$419 nightly
The price is $472
Feb 8 - Feb 9
Total with taxes and fees
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Exterior

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.6 out of 10, Exceptional, (8 reviews)
"Wonderful place to stay overnight. Nice furnishings. Good room layout for family. Convenience of washer and dryer. Host was quick and responsive. Thank you for a terrific stay."
United States
George L.
$246 nightly
The price is $276
Feb 9 - Feb 10
Total with taxes and fees
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Interior

Encore Swanky

Encore Swanky
3.0 star property
Kissimmee
$443 nightly
The price is $503
Feb 13 - Feb 14
Total with taxes and fees
Encore Swanky
Exterior

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Davenport
5.0 out of 10, (2 reviews)
"Needs some upgrades. The bed was a full size, very small for a couple, should really think of upgrading to a king. Pans were old and could use replacing. Bugs and ants constant. Shower was small. Very small tv. Stovetop had missing nob and was difficult to operate. Definitely needs upgrading, left a day early, didn’t feel comfortable there. "
United States
Rebecca F.
$132 nightly
The price is $146
Feb 8 - Feb 9
Total with taxes and fees
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Exterior

Sun Baked Cottage with Hot Tub near Disney with Margaritaville Resort & Island.

Sun Baked Cottage with Hot Tub near Disney with Margaritaville Resort & Island.
Kissimmee
$435 nightly
The price is $487
Mar 2 - Mar 3
Total with taxes and fees
Sun Baked Cottage with Hot Tub near Disney with Margaritaville Resort & Island.
Exterior

Playa Verde Cottage with Private Hot Tub near Disney with Margaritaville Resort.

Playa Verde Cottage with Private Hot Tub near Disney with Margaritaville Resort.
Kissimmee
$435 nightly
The price is $487
Mar 2 - Mar 3
Total with taxes and fees
Playa Verde Cottage with Private Hot Tub near Disney with Margaritaville Resort.
Exterior

Lovely Cottage 3 miles from Disney w/ Hot Tub and Margaritaville Resort &.

Lovely Cottage 3 miles from Disney w/ Hot Tub and Margaritaville Resort &.
Kissimmee
$435 nightly
The price is $487
Mar 2 - Mar 3
Total with taxes and fees
Lovely Cottage 3 miles from Disney w/ Hot Tub and Margaritaville Resort &.
Exterior

Cozy Cottage with Hot Tub Near Disney with Margaritaville Resort & Island H2O.

Cozy Cottage with Hot Tub Near Disney with Margaritaville Resort & Island H2O.
Kissimmee
$436 nightly
The price is $488
Mar 3 - Mar 4
Total with taxes and fees
Cozy Cottage with Hot Tub Near Disney with Margaritaville Resort & Island H2O.
Property grounds

Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (19 reviews)
"Will definitely be staying again"
United States
Tom W.
$232 nightly
The price is $254
Feb 10 - Feb 11
Total with taxes and fees
Cozy Lake Front Cottage
Interior

4716-4-ww-blend of Relaxation and Convenience

4716-4-ww-blend of Relaxation and Convenience
2.0 star property
Windward Cay
$2,652 nightly
The price is $3,010
Feb 28 - Mar 1
Total with taxes and fees
4716-4-ww-blend of Relaxation and Convenience
Interior

Orlando Theme Park Basecamp: Family Home w/ Patio

Orlando Theme Park Basecamp: Family Home w/ Patio
3.0 star property
Davenport
$328 nightly
The price is $364
Feb 8 - Feb 9
Total with taxes and fees
Orlando Theme Park Basecamp: Family Home w/ Patio
Exterior

Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.

Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
$434 nightly
The price is $486
Mar 2 - Mar 3
Total with taxes and fees
Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.
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

Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG

10/10 Excellent
"The rooms were pretty cool. The staff was nice and the game room. The kids loved the game room lol"
Justin 1-night trip
Posted 22 hours ago
Holiday Inn Resort Orlando Suites - Waterpark by IHG

Find out more about Windermere

Windermere Cottages information

Number of reviews
56
Accommodation
1829 Cottages
Lowest Price
$146
Highest Price
$503

Frequently asked questions

How much do cottages in Windermere cost?
Rates for cottages in Windermere range between $146 and $503 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.
Are there any family-friendly cottages in Windermere?
If you want to slow the pace down a notch in Windermere, you can't go past Fresh And Remodeled In Vista Cay Townhome. With a 3-star rating and amenities like a barbecue grill and a picnic area, you'll find it easy to settle in at this family-friendly cottage. Windermere boasts plenty of family-friendly attractions to visit when the kids are getting restless. Walt Disney World® Resort and Universal Studios Florida guarantee a fun day out for young and old.
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.
What is there to do in Windermere near my cottage?
After you've unpacked your things and settled in, head out and discover the fantastic things Windermere has for you to experience. Isleworth Golf and Country Club is a great attraction to add to your to-do list.

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