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 23 - Aug 24
Total with taxes and fees
Shore Steps Cottage - Walking Distance To The Town Of Windermere

2. Cozy 1-bedroom tiny home minutes from Disney, SeaWorld, and Universal!

Cozy 1-bedroom tiny home minutes from Disney, SeaWorld, and Universal!
Kissimmee
$74 nightly
The price is $81
Aug 24 - Aug 25
Total with taxes and fees
Cozy 1-bedroom tiny home minutes from Disney, SeaWorld, and Universal!

3. Pond Access & Grill! Group Escape, 19 Mi to WDW

Pond Access & Grill! Group Escape, 19 Mi to WDW
3.0 star property
Kissimmee
$302 nightly
The price is $343
Aug 23 - Aug 24
Total with taxes and fees
Pond Access & Grill! Group Escape, 19 Mi to WDW
A multi-story residential building with balconies, a lawn, and outdoor seating.

4. 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 house with a red door, a front porch, and a pathway leading to the entrance.

5. 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.

6. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
$178 nightly
The price is $198
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.

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, (47 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 13 - Sep 14
Total with taxes and fees
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
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
$187 nightly
The price is $209
Aug 23 - Aug 24
Total with taxes and fees
Newly Remodeled Tiny Home 20 minutes from Disney!~
A residential area with houses featuring sloped roofs and solar panels.

9. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
$224 nightly
The price is $254
Aug 26 - Aug 27
Total with taxes and fees
Upstay: Bright Family-friendly Retreat With Patio
A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

10. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
$345 nightly
The price is $383
Aug 23 - Aug 24
Total with taxes and fees
Serenity - Family & Pet Friendly, Amazing Location
A house with a porch, surrounded by a grassy area and a pond with lily pads.

11. 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
$328 nightly
The price is $362
Sep 1 - Sep 2
Total with taxes and fees
Incredible Private Lakefront Cottage Retreat
A mobile home with a paved driveway, a lawn, and a golf cart parked in front.

12. 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 two-story house with a front porch, a brick driveway, and a well-maintained lawn.

13. 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 resort with multiple buildings, a large swimming pool, and a lake in the background.

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

Th89 - 3BR House Near Disney With Resort Access
3.0 star property
Orlando
$416 nightly
The price is $467
Sep 6 - Sep 7
Total with taxes and fees
Th89 - 3BR House Near Disney With Resort Access
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
$210 nightly
The price is $233
Aug 24 - Aug 25
Total with taxes and fees
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
A kitchen with white cabinets, a granite countertop, a stainless steel sink, and a black microwave.

16. 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
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.
$183 nightly
The price is $205
Aug 31 - Sep 1
Total with taxes and fees
Family-Friendly Cottage Near Orlando’s Top Attractions
A hammock tied between two wooden posts, a wooden deck, and a view of a lake with trees and a clear sky.

18. 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 single-story house with a gabled roof, a front porch, and a small front yard with a large agave plant.

19. 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.

20. 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
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

Marriott's Grande Vista

Marriott's Grande Vista

8/10 Good
"Room was clean. Parking was good and accessible. Pools were fine. Bar was what you’d expect for premium drinks."
Michael 2-night trip
Posted less than an hour ago
Marriott's Grande Vista

Find out more about Windermere

Windermere Cottages information

Number of reviews
Accommodation
2491 Cottages
Lowest Price
$254
Highest Price
$836

Frequently asked questions

How much do cottages in Windermere cost?
Rates for cottages in Windermere range between $254 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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