A lakeside community with houses and boats.

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Windermere cottages

Property grounds

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)
$330 nightly
The price is $367
Sep 10 - Sep 11
Total with taxes and fees
Shore Steps Cottage - Walking Distance To The Town Of Windermere
House (2 Bedrooms) | Interior

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
Sep 20 - Sep 21
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!
Exterior detail

3. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (15 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
$155 nightly
The price is $171
Sep 10 - Sep 11
Total with taxes and fees
Downtown Cottage
Property grounds

4. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
$177 nightly
The price is $196
Sep 10 - Sep 11
Total with taxes and fees
Romantic Lakefront Getaway with Balcony near Downtown Orlando
Property grounds

5. Th89 - 3BR House Near Disney With Resort Access

Th89 - 3BR House Near Disney With Resort Access
3.0 star property
Orlando
Th89 - 3BR House Near Disney With Resort Access
Exterior

6. Enchanted Cottage with Pool and Mini-Golf Near Disney

Enchanted Cottage with Pool and Mini-Golf Near Disney
Kissimmee
9.4 out of 10, Exceptional, (42 reviews)
"This place was the perfect little hideaway during our trip to the parks. Would most definitely stay again."
United States
Shane B.
$161 nightly
The price is $180
Sep 17 - Sep 18
Total with taxes and fees
Enchanted Cottage with Pool and Mini-Golf Near Disney
Exterior

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, (51 reviews)
"Everything was super clean and exactly as described. Great location and great stay!"
United States
Garrett S.
$292 nightly
The price is $324
Sep 28 - Sep 29
Total with taxes and fees
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Property grounds

8. Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (25 reviews)
"The setting was very nice and in a quiet area, but conveniently located to travel around Florida. Cottage was clean and very comfortable. Would definitely stay again."
United States
Brenda P.
$264 nightly
The price is $290
Sep 10 - Sep 11
Total with taxes and fees
Cozy Lake Front Cottage
Exterior

9. 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
Sep 10 - Sep 11
Total with taxes and fees
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Exterior

10. 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
Sep 10 - Sep 11
Total with taxes and fees
Perfect Place for a Perfect Vacation
House (3 Bedrooms) | Interior

11. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
$232 nightly
The price is $263
Sep 29 - Sep 30
Total with taxes and fees
Upstay: Bright Family-friendly Retreat With Patio
Exterior

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

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
$186 nightly
The price is $208
Sep 10 - Sep 11
Total with taxes and fees
Newly Remodeled Tiny Home 20 minutes from Disney!~
Exterior

13. Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
3.0 star property
Kissimmee
$736 nightly
The price is $836
Sep 13 - Sep 14
Total with taxes and fees
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
Microwave, stovetop

14. Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.4 out of 10, Very Good, (9 reviews)
"Proximity to theme parks, restaurants, and shopping"
United States
NOLI
$151 nightly
The price is $168
Sep 14 - Sep 15
Total with taxes and fees
Tiny house close to Disney KISSIMMEE
Property grounds

15. Th20 - 3BR House With Resort Access Near Parks

Th20 - 3BR House With Resort Access Near Parks
3.0 star property
Orlando
$416 nightly
The price is $467
Sep 17 - Sep 18
Total with taxes and fees
Th20 - 3BR House With Resort Access Near Parks
Smart TV, books

16. 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.
$182 nightly
The price is $204
Sep 20 - Sep 21
Total with taxes and fees
Family-Friendly Cottage Near Orlando’s Top Attractions
House (4 Bedrooms) | Interior

17. ~ 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 $476
Sep 10 - Sep 11
Total with taxes and fees
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Dining

18. 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
$196 nightly
The price is $219
Sep 22 - Sep 23
Total with taxes and fees
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Exterior

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

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.4 out of 10, Exceptional, (13 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
$235 nightly
The price is $263
Sep 13 - Sep 14
Total with taxes and fees
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Exterior

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
Sep 10 - Sep 11
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
"Everything about our stay was excellent! No complaints."
Pedro 2-night trip
Posted 2 hours ago
Kompose Boutique Resort at Theme Parks

Find out more about Windermere

Windermere Cottages information

Number of reviews
143
Accommodation
2491 Cottages
Lowest Price
$156
Highest Price
$836

Frequently asked questions

How much do cottages in Windermere cost?
Rates for cottages in Windermere range between $156 and $836 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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