A lakeside community with houses and boats.

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Windermere cottages

A serene landscape with a pond, trees with Spanish moss, and a palm tree.

1. Shore Steps Cottage - Walking Distance To The Town Of Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere
Windermere
10.0 out of 10, Exceptional, (1 review)
$323 nightly
The price is $359
Oct 29 - Oct 30
Total with taxes and fees
Shore Steps Cottage - Walking Distance To The Town Of Windermere
A two-story house with a front porch, a brick driveway, and a well-maintained lawn.

2. Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
$444 nightly
The price is $499
Nov 3 - Nov 4
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!
A modern kitchen with red walls, a dining area with a brown leather couch, and a bar stool.

3. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (16 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
$163 nightly
The price is $181
Oct 29 - Oct 30
Total with taxes and fees
Downtown Cottage
A resort with multiple swimming pools, palm trees, and a large building with a red-tiled roof.

4. Th10 - 3BR House Near Disney and Universal Studios

Th10 - 3BR House Near Disney and Universal Studios
3.0 star property
Orlando
$422 nightly
The price is $474
Nov 1 - Nov 2
Total with taxes and fees
Th10 - 3BR House Near Disney and Universal Studios
A residential area with houses featuring sloped roofs and solar panels.

5. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
$221 nightly
The price is $251
Nov 3 - Nov 4
Total with taxes and fees
Upstay: Bright Family-friendly Retreat With Patio
A table with a potted plant and a cup of coffee, overlooking a scenic landscape.

6. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
$181 nightly
The price is $201
Nov 1 - Nov 2
Total with taxes and fees
Romantic Lakefront Getaway with Balcony near Downtown Orlando
A white building with large windows and a brick pathway leading to it.

7. 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, (55 reviews)
"Everything was super clean and exactly as described. Great location and great stay!"
United States
Garrett S.
$287 nightly
The price is $319
Nov 2 - Nov 3
Total with taxes and fees
The Coach House- Entire Home - 2 bedroom/3 bath - Orlando Getaway!
A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

8. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
$356 nightly
The price is $395
Oct 29 - Oct 30
Total with taxes and fees
Serenity - Family & Pet Friendly, Amazing Location
A mobile home with a paved driveway, a lawn, and a golf cart parked in front.

9. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
$171 nightly
The price is $191
Nov 1 - Nov 2
Total with taxes and fees
Perfect Place for a Perfect Vacation
A single-story house with a white exterior, a front door, and a garage.

10. 9 Mi to Walt Disney World: Family Home w/ Pool!

9 Mi to Walt Disney World: Family Home w/ Pool!
3.0 star property
Clear Creek
$333 nightly
The price is $369
Nov 22 - Nov 23
Total with taxes and fees
9 Mi to Walt Disney World: Family Home w/ Pool!
A modern living room with a sofa, a large wall clock, and a mirror.

11. 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.
$185 nightly
The price is $207
Nov 2 - Nov 3
Total with taxes and fees
Family-Friendly Cottage Near Orlando’s Top Attractions
A single-story house with a gabled roof, a front porch, and a small front yard with a large agave plant.

12. 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.
$274 nightly
The price is $307
Nov 1 - Nov 2
Total with taxes and fees
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
A compact kitchen with a built-in TV, a dining area with a bench, and a wall decorated with motivational posters.

13. 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
$195 nightly
The price is $218
Nov 1 - Nov 2
Total with taxes and fees
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
A resort with multiple swimming pools, palm trees, and a large building with a red-tiled roof.

14. Th60 - 3BR House Near Disney With Pool Access

Th60 - 3BR House Near Disney With Pool Access
3.0 star property
Orlando
$440 nightly
The price is $495
Nov 9 - Nov 10
Total with taxes and fees
Th60 - 3BR House Near Disney With Pool Access
An aerial view of a resort with multiple swimming pools, palm trees, and a golf course.

15. Upstay Disney 5BR Movie Mansionwindsor Cay Resort

Upstay Disney 5BR Movie Mansionwindsor Cay Resort
3.0 star property
Clermont
Upstay Disney 5BR Movie Mansionwindsor Cay Resort
A single-story mobile home with a front porch and a small deck.

16. Newly Remodeled Tiny Home 20 minutes from Disney!~

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
$186 nightly
The price is $208
Nov 1 - Nov 2
Total with taxes and fees
Newly Remodeled Tiny Home 20 minutes from Disney!~
A hammock tied between two wooden posts, a wooden deck, and a view of a lake with trees and a clear sky.

17. Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (27 reviews)
"Very nice cottage, beautiful view"
United States
rachel c.
$281 nightly
The price is $308
Oct 29 - Oct 30
Total with taxes and fees
Cozy Lake Front Cottage
A restaurant with outdoor seating and a thatched roof.

18. "Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.4 out of 10, Exceptional, (14 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
$355 nightly
The price is $398
Nov 20 - Nov 21
Total with taxes and fees
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
A lakeside patio with wooden rocking chairs and a table, overlooking a calm lake and a forested area.

19. Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
Orlando
$215 nightly
The price is $239
Oct 29 - Oct 30
Total with taxes and fees
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
A small cabin with a porch and a garage, surrounded by trees and a clear sky.

20. Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney

Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
Davenport
6.8 out of 10, (3 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.
$141 nightly
The price is $156
Oct 29 - Oct 30
Total with taxes and fees
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
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

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

10/10 Excellent
"I thoroughly enjoyed the hotel stay, rooms were spacious. Staff was amazing. Would definitely recommend this hotel to others"
Nickara 2-night trip
Posted 2 hours ago
Kompose Boutique Resort at Theme Parks

Find out more about Windermere

Windermere Cottages information

Number of reviews
115
Accommodation
2712 Cottages
Lowest Price
$156
Highest Price
$499

Frequently asked questions

How much do cottages in Windermere cost?
Rates for cottages in Windermere range between $156 and $499 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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