A lakeside community with houses and boats.

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

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)
$335 nightly
The price is $372
Aug 24 - Aug 25
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
Aug 27 - Aug 28
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!
A house with a red door, a front porch, and a pathway leading to the entrance.

3. Downtown Cottage

Downtown Cottage
Colonialtown North
8.6 out of 10, Excellent, (14 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
$150 nightly
The price is $167
Aug 24 - Aug 25
Total with taxes and fees
Downtown Cottage
A table with a potted plant and a cup of coffee, overlooking a scenic landscape.

4. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
$175 nightly
The price is $194
Aug 26 - Aug 27
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.

5. 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, (47 reviews)
"Everything was super clean and exactly as described. Great location and great stay!"
United States
Garrett S.
$294 nightly
The price is $326
Sep 13 - Sep 14
Total with taxes and fees
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
A residential area with houses featuring sloped roofs and solar panels.

6. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
$220 nightly
The price is $249
Aug 24 - Aug 25
Total with taxes and fees
Upstay: Bright Family-friendly Retreat With Patio
A mobile home with a paved driveway, a lawn, and a golf cart parked in front.

7. 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
Aug 24 - Aug 25
Total with taxes and fees
Perfect Place for a Perfect Vacation
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
$347 nightly
The price is $385
Aug 24 - Aug 25
Total with taxes and fees
Serenity - Family & Pet Friendly, Amazing Location
A modern living room with a sofa, a large wall clock, and a mirror.

9. 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.
$183 nightly
The price is $205
Aug 31 - Sep 1
Total with taxes and fees
Family-Friendly Cottage Near Orlando’s Top Attractions
A kitchen with white cabinets, a granite countertop, a stainless steel sink, and a black microwave.

10. 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
$148 nightly
The price is $165
Sep 1 - Sep 2
Total with taxes and fees
Tiny house close to Disney KISSIMMEE
An aerial view of a resort with multiple swimming pools, a dock, and a residential area with houses.

11. 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 20 - Sep 21
Total with taxes and fees
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
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.
$278 nightly
The price is $311
Sep 1 - Sep 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
$198 nightly
The price is $221
Aug 31 - Sep 1
Total with taxes and fees
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
A row of two-story houses with a front porch, a small garden with various plants, and a clear blue sky.

14. Pastel Paradise Villa near Disney With Margaritaville Resort and Island H20.

Pastel Paradise Villa near Disney With Margaritaville Resort and Island H20.
Kissimmee
$456 nightly
The price is $510
Aug 26 - Aug 27
Total with taxes and fees
Pastel Paradise Villa near Disney With Margaritaville Resort and Island H20.
A two-story residential building with a central entrance, a small balcony, and a well-maintained garden with various plants and a palm tree.

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

Crystal Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
$484 nightly
The price is $542
Aug 26 - Aug 27
Total with taxes and fees
Crystal Cottage near Disney with Margaritaville Resort & Island H2O Access -.
A hammock tied between two wooden posts, a wooden deck, and a view of a lake with trees and a clear sky.

16. 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.
$268 nightly
The price is $294
Aug 24 - Aug 25
Total with taxes and fees
Cozy Lake Front Cottage
A row of coastal-style buildings with balconies, a clear sky, and a well-maintained garden.

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

Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
$482 nightly
The price is $539
Aug 26 - Aug 27
Total with taxes and fees
Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.
A two-story building with a balcony, a small porch, and a parking lot in front.

18. Livin' for the Weekend Cottage near Disney with Island H2O Access - 8021FF

Livin' for the Weekend Cottage near Disney with Island H2O Access - 8021FF
Kissimmee
$484 nightly
The price is $542
Aug 30 - Aug 31
Total with taxes and fees
Livin' for the Weekend Cottage near Disney with Island H2O Access - 8021FF
A restaurant with outdoor seating and a thatched roof.

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

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.4 out of 10, Exceptional, (12 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
$238 nightly
The price is $266
Aug 27 - Aug 28
Total with taxes and fees
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
A row of colorful houses with a parking lot in front.

20. Breezy Green Cottage with Private Hot Tub near Disney with Margaritaville.

Breezy Green Cottage with Private Hot Tub near Disney with Margaritaville.
Kissimmee
8.0 out of 10, Very Good, (1 review)
"We’ve stayed at Margaritaville at least 4-5 times in different houses and we always have a great time. This house had a great location, as it was close to the gym and pool area. Negatives: on the listing it says there is a king bed, definitely no king bed. The first night was cold and none of the beds had anything other than sheets and when we called and requested additional blankets, we were told it was going to be $10 each blanket! The room did not come with sheets for the pull out couch so...
United States
Chad A.
$484 nightly
The price is $542
Aug 30 - Aug 31
Total with taxes and fees
Breezy Green Cottage with Private Hot Tub near Disney with Margaritaville.
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

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

8/10 Good
"The water park was well maintained and my son had an amazing time. The pools were clean and the staff was very friendly and attentive. The rooms are clean and very spacious. I would stay here again."
Monica 5-night trip
Posted 3 hours ago
The Grove Resort & Water Park Orlando

Find out more about Windermere

Windermere Cottages information

Number of reviews
97
Accommodation
2491 Cottages
Lowest Price
$165
Highest Price
$836

Frequently asked questions

How much do cottages in Windermere cost?
Rates for cottages in Windermere range between $165 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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