A lakeside community with houses and boats.

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

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
$330 nightly
The price is $367
Aug 8 - Aug 9
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
Aug 9 - Aug 10
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!
Exterior detail

3. Downtown Cottage

Downtown Cottage
Colonialtown North
8.4 out of 10, Very Good, (12 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
$155 nightly
The price is $171
Aug 9 - Aug 10
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
$204 nightly
The price is $226
Aug 9 - Aug 10
Total with taxes and fees
Romantic Lakefront Getaway with Balcony near Downtown Orlando
Property grounds

5. Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (24 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
Aug 8 - Aug 9
Total with taxes and fees
Cozy Lake Front Cottage
Exterior

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

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
$185 nightly
The price is $207
Aug 8 - Aug 9
Total with taxes and fees
Newly Remodeled Tiny Home 20 minutes from 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, (44 reviews)
"The place was great overall, had everything needed. Rooms and bathrooms were spacious. Hosts left goodies for the stay, communicated what was needed, and made the check-in/check-out process very easy. Would stay again. It was perfect distance from Kia Center (5 min drive) "
United States
M L.
$313 nightly
The price is $347
Aug 23 - Aug 24
Total with taxes and fees
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
House (3 Bedrooms) | Interior

8. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
$364 nightly
The price is $404
Aug 8 - Aug 9
Total with taxes and fees
Serenity - Family & Pet Friendly, Amazing Location
House (3 Bedrooms) | Interior

9. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
$244 nightly
The price is $276
Aug 20 - Aug 21
Total with taxes and fees
Upstay: Bright Family-friendly Retreat With Patio
Dining

10. 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
Aug 11 - Aug 12
Total with taxes and fees
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Exterior

11. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
$180 nightly
The price is $202
Aug 31 - Sep 1
Total with taxes and fees
Perfect Place for a Perfect Vacation
Exterior

12. Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (38 reviews)
"Beautiful property in a fantastic location! We've booking this stay twice and will be back again."
United States
Lisa
$343 nightly
The price is $379
Aug 23 - Aug 24
Total with taxes and fees
Incredible Private Lakefront Cottage Retreat
Microwave, stovetop

13. 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
$174 nightly
The price is $195
Aug 31 - Sep 1
Total with taxes and fees
Tiny house close to Disney KISSIMMEE
Exterior

14. 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.
$277 nightly
The price is $310
Sep 1 - Sep 2
Total with taxes and fees
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Smart TV, books

15. 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 7 - Sep 8
Total with taxes and fees
Family-Friendly Cottage Near Orlando’s Top Attractions
Exterior

16. 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
$780 nightly
The price is $885
Aug 11 - Aug 12
Total with taxes and fees
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
Property grounds

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

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
Orlando
$205 nightly
The price is $228
Sep 1 - Sep 2
Total with taxes and fees
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
Exterior

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

Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
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.
$141 nightly
The price is $156
Aug 8 - Aug 9
Total with taxes and fees
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
House (4 Bedrooms) | Interior

19. ~ 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
Aug 21 - Aug 22
Total with taxes and fees
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Exterior

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

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.4 out of 10, Exceptional, (11 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
$256 nightly
The price is $287
Aug 9 - Aug 10
Total with taxes and fees
"Casa Kiwi" Margaritaville Cottage 5 minutes 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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Only thing little far from all the attractions otherwise very nice, clean and comfortable accommodation."
DINESH 2-night trip
Posted 2 hours ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Find out more about Windermere

Windermere Cottages information

Number of reviews
143
Accommodation
2205 Cottages
Lowest Price
$156
Highest Price
$885

Frequently asked questions

How much do cottages in Windermere cost?
Rates for cottages in Windermere range between $156 and $885 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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