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

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)
$331 nightly
The price is $368
Sep 12 - Sep 13
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
Sep 20 - Sep 21
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
8.8 out of 10, Excellent, (15 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
$151 nightly
The price is $168
Sep 13 - Sep 14
Total with taxes and fees
Downtown Cottage
A resort with a swimming pool, parking, and a view of a lake.

4. 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
A table with a potted plant and a cup of coffee, overlooking a scenic landscape.

5. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
$174 nightly
The price is $194
Sep 13 - Sep 14
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.

6. 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, (52 reviews)
"Everything was super clean and exactly as described. Great location and great stay!"
United States
Garrett S.
$291 nightly
The price is $323
Sep 28 - Sep 29
Total with taxes and fees
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
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)
$164 nightly
The price is $184
Sep 12 - Sep 13
Total with taxes and fees
Perfect Place for a Perfect Vacation
A single-story mobile home with a front porch and a small deck.

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

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
$179 nightly
The price is $201
Sep 12 - Sep 13
Total with taxes and fees
Newly Remodeled Tiny Home 20 minutes from Disney!~
A covered outdoor area with a concrete floor, surrounded by grass and trees.

9. 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.
$167 nightly
The price is $186
Sep 17 - Sep 18
Total with taxes and fees
Enchanted Cottage with Pool and Mini-Golf Near Disney
An aerial view of a resort with multiple swimming pools, a dock, and a residential area with houses.

10. 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
$733 nightly
The price is $833
Sep 21 - Sep 22
Total with taxes and fees
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
A kitchen with white cabinets, a granite countertop, a stainless steel sink, and a black microwave.

11. 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
$152 nightly
The price is $169
Sep 14 - Sep 15
Total with taxes and fees
Tiny house close to Disney KISSIMMEE
A residential area with houses featuring sloped roofs and solar panels.

12. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
$227 nightly
The price is $258
Sep 30 - Oct 1
Total with taxes and fees
Upstay: Bright Family-friendly Retreat With Patio
A hammock tied between two wooden posts, a wooden deck, and a view of a lake with trees and a clear sky.

13. 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 13 - Sep 14
Total with taxes and fees
Cozy Lake Front Cottage
A multi-story residential building with balconies, a lawn, and outdoor seating.

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

Th10 - 3BR House Near Disney and Universal Studios
3.0 star property
Orlando
$417 nightly
The price is $469
Sep 14 - Sep 15
Total with taxes and fees
Th10 - 3BR House Near Disney and Universal Studios
A lakeside patio with wooden rocking chairs and a table, overlooking a calm lake and a forested area.

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

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
Orlando
$201 nightly
The price is $224
Sep 13 - Sep 14
Total with taxes and fees
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
A single-story house with a gabled roof, a front porch, and a small front yard with a large agave plant.

16. 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.
$272 nightly
The price is $305
Sep 27 - Sep 28
Total with taxes and fees
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
A modern living room with a sofa, a large wall clock, and a mirror.

17. 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.
$181 nightly
The price is $203
Sep 14 - Sep 15
Total with taxes and fees
Family-Friendly Cottage Near Orlando’s Top Attractions
A single-story house with a brick facade, a garage, and a well-maintained lawn.

18. ~ 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 12 - Sep 13
Total with taxes and fees
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
A compact kitchen with a built-in TV, a dining area with a bench, and a wall decorated with motivational posters.

19. 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
$188 nightly
The price is $211
Sep 22 - Sep 23
Total with taxes and fees
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
A restaurant with outdoor seating and a thatched roof.

20. "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
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 Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"N_A"
Miguel Angel 4-night trip
Posted less than an hour ago
Universal's Cabana Bay Beach Resort

Find out more about Windermere

Windermere Cottages information

Number of reviews
144
Accommodation
2491 Cottages
Lowest Price
$168
Highest Price
$833

Frequently asked questions

How much do cottages in Windermere cost?
Rates for cottages in Windermere range between $168 and $833 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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