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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Windermere cottages

Interior

Downtown Cottage

Downtown Cottage
Colonialtown North
8.0 out of 10, Very Good, (10 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
$158 nightly
The price is $175
Mar 29 - Mar 30
Total with taxes and fees
Downtown Cottage
Property grounds

Tiny Hidden Cottage

Tiny Hidden Cottage
Longwood
9.4 out of 10, Exceptional, (63 reviews)
"Great little cottage, it was easy to locate and access the property. Nice quiet area and we really enjoyed our stay."
United States
Anna M.
$131 nightly
The price is $144
Mar 31 - Apr 1
Total with taxes and fees
Tiny Hidden Cottage
Interior

Red Jordan Boho Style Vacation Home

Red Jordan Boho Style Vacation Home
3.0 star property
Meadow Woods
Red Jordan Boho Style Vacation Home
Property grounds

Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
$206 nightly
The price is $229
Apr 6 - Apr 7
Total with taxes and fees
Romantic Lakefront Getaway with Balcony near Downtown Orlando
Exterior

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (33 reviews)
"The host was easy to contact and the cottage was very cozy with all necessary amenities. The lakeside location was both beautiful and peaceful, especially considering it is so close to 436 and I4. We definitely plan to return. "
United States
Carol G.
$384 nightly
The price is $425
Apr 5 - Apr 6
Total with taxes and fees
Incredible Private Lakefront Cottage Retreat
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, (35 reviews)
"Lovely spot, in a quiet neighborhood. Clean and spotless, and stocked with amenities for breakfast and snacks. We'll be booking again next time we go down to visit family in Orlando."
United States
John
$284 nightly
The price is $317
Apr 2 - Apr 3
Total with taxes and fees
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Property grounds

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
Orlando
$228 nightly
The price is $254
Mar 29 - Mar 30
Total with taxes and fees
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
House (2 Bedrooms) | Interior

Chic Orlando Family Getaway w/ Fenced Yard!

Chic Orlando Family Getaway w/ Fenced Yard!
3.0 star property
Rosemont
10.0 out of 10, Exceptional, (1 review)
$469 nightly
The price is $525
Apr 9 - Apr 10
Total with taxes and fees
Chic Orlando Family Getaway w/ Fenced Yard!
Microwave, stovetop

Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.4 out of 10, Very Good, (6 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.
$164 nightly
The price is $183
Apr 13 - Apr 14
Total with taxes and fees
Tiny house close to Disney KISSIMMEE
Exterior

Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
$175 nightly
The price is $195
Apr 8 - Apr 9
Total with taxes and fees
Perfect Place for a Perfect Vacation
Smart TV, books

Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"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.
$186 nightly
The price is $208
Apr 21 - Apr 22
Total with taxes and fees
Family-Friendly Cottage Near Orlando’s Top Attractions
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.
$246 nightly
The price is $276
Apr 21 - Apr 22
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
$194 nightly
The price is $217
Mar 29 - Mar 30
Total with taxes and fees
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
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.
$169 nightly
The price is $187
Mar 30 - Mar 31
Total with taxes and fees
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Interior

Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
Serenity - Family & Pet Friendly, Amazing Location
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)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
$262 nightly
The price is $294
Apr 6 - Apr 7
Total with taxes and fees
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Property grounds

Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.

Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.
Kissimmee
$513 nightly
The price is $574
Apr 13 - Apr 14
Total with taxes and fees
Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.
House (2 Bedrooms) | Interior

Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
$455 nightly
The price is $509
Apr 2 - Apr 3
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!
Exterior

Sunny Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.

Sunny Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
Kissimmee
$507 nightly
The price is $568
Apr 21 - Apr 22
Total with taxes and fees
Sunny Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
Exterior

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

Crystal Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
$427 nightly
The price is $478
Apr 21 - Apr 22
Total with taxes and fees
Crystal 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

Universal's Endless Summer Resort - Dockside Inn and Suites

Universal's Endless Summer Resort - Dockside Inn and Suites

8/10 Good
"To bad the food isn’t less expensive "
Vanessa 4-night trip
Posted 1 hour ago
Universal's Endless Summer Resort - Dockside Inn and Suites

Find out more about Windermere

Windermere Cottages information

Number of reviews
62
Accommodation
1830 Cottages
Lowest Price
$144
Highest Price
$574

Frequently asked questions

How much do cottages in Windermere cost?
Rates for cottages in Windermere range between $144 and $574 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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