A lakeside community with houses and boats.

Search Windermere Cottage Rentals from CA $222

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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)
The price is CA $230
CA $563 total
includes taxes & fees
Oct 6 - Oct 7
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
The price is CA $284
CA $711 total
includes taxes & fees
Oct 18 - Oct 19
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.
The price is CA $103
CA $265 total
includes taxes & fees
Oct 11 - Oct 12
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
The price is CA $117
CA $288 total
includes taxes & fees
Nov 3 - Nov 4
Romantic Lakefront Getaway with Balcony near Downtown Orlando
Exterior

5. Gorgeous Cottage near Lake Louisa & mins 2 Disney.

Gorgeous Cottage near Lake Louisa & mins 2 Disney.
Vacation Village
9.4 out of 10, Exceptional, (65 reviews)
"Wonderful time at a property just right for our needs and wants. "
United States
Peter C.
The price is CA $177
CA $225 total
includes taxes & fees
Oct 8 - Oct 9
Gorgeous Cottage near Lake Louisa & mins 2 Disney.
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, (54 reviews)
"Everything was super clean and exactly as described. Great location and great stay!"
United States
Garrett S.
The price is CA $225
CA $470 total
includes taxes & fees
Oct 12 - Oct 13
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
A multi-story residential building with balconies, a lawn, and outdoor seating.

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

Th10 - 3BR House Near Disney and Universal Studios
3.0 star property
Orlando
The price is CA $351
CA $699 total
includes taxes & fees
Oct 28 - Oct 29
Th10 - 3BR House Near Disney and Universal Studios
A residential area with houses featuring sloped roofs and solar panels.

8. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is CA $107
CA $362 total
includes taxes & fees
Oct 19 - Oct 20
Upstay: Bright Family-friendly Retreat With Patio
A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

9. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is CA $132
CA $566 total
includes taxes & fees
Oct 6 - Oct 7
Serenity - Family & Pet Friendly, Amazing Location
A mobile home with a paved driveway, a lawn, and a golf cart parked in front.

10. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is CA $115
CA $276 total
includes taxes & fees
Oct 6 - Oct 7
Perfect Place for a Perfect Vacation
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
The price is CA $83
CA $228 total
includes taxes & fees
Oct 7 - Oct 8
Tiny house close to Disney KISSIMMEE
A residential house with a front yard, a palm tree, and a garage.

12. Chic Orlando Family Getaway w/ Fenced Yard!

Chic Orlando Family Getaway w/ Fenced Yard!
3.0 star property
Rosemont
10.0 out of 10, Exceptional, (2 reviews)
"The house was well supplied with amenities, family friendly and it was very fun to use the pool and games. There’s a super Walmart and other shops close by."
United States
Jennifer
The price is CA $261
CA $794 total
includes taxes & fees
Oct 15 - Oct 16
Chic Orlando Family Getaway w/ Fenced Yard!
A modern living room with a sofa, a large wall clock, and a mirror.

13. 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.
The price is CA $128
CA $292 total
includes taxes & fees
Oct 6 - Oct 7
Family-Friendly Cottage Near Orlando’s Top Attractions
A single-story house with a gabled roof, a front porch, and a small front yard with a large agave plant.

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.
The price is CA $134
CA $443 total
includes taxes & fees
Oct 6 - Oct 7
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
A single-story mobile home with a front porch and a small deck.

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

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
The price is CA $121
CA $301 total
includes taxes & fees
Oct 6 - Oct 7
Newly Remodeled Tiny Home 20 minutes from Disney!~
A compact kitchen with a built-in TV, a dining area with a bench, and a wall decorated with motivational posters.

16. 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
The price is CA $132
CA $312 total
includes taxes & fees
Oct 11 - Oct 12
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
A resort with a large central pool, a smaller circular pool, and a fountain. There are multiple buildings with balconies and a parking lot.

17. Th130 - 3BR House Near Disney and Universal Parks

Th130 - 3BR House Near Disney and Universal Parks
3.0 star property
Orlando
The price is CA $322
CA $666 total
includes taxes & fees
Oct 12 - Oct 13
Th130 - 3BR House Near Disney and Universal Parks
A two-story house with a garage, surrounded by well-maintained lawns and palm trees.

18. Family Resort Home w Pool, BBQ & Game Room

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is CA $160
CA $480 total
includes taxes & fees
Oct 18 - Oct 19
Family Resort Home w Pool, BBQ & Game Room
A small cabin with a porch and a garage, surrounded by trees and a clear sky.

19. 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.
The price is CA $101
CA $222 total
includes taxes & fees
Oct 6 - Oct 7
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
A single-story house with a covered patio area, a lawn, and a clear sky.

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

Pond Access & Grill! Group Escape, 19 Mi to WDW
3.0 star property
Kissimmee
The price is CA $209
CA $287 total
includes taxes & fees
Oct 6 - Oct 7
Pond Access & Grill! Group Escape, 19 Mi to WDW
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windermere Hotel Reviews

Universal's Endless Summer Resort - Dockside Inn and Suites

Universal's Endless Summer Resort - Dockside Inn and Suites

10/10 Excellent
"Best hotel when visiten Universal Orlando Parks. Easy bus riding to parks and City Walk."
Jose 4-night trip
Posted less than an hour ago
Universal's Endless Summer Resort - Dockside Inn and Suites

Find out more about Windermere

Windermere Cottages information

Number of reviews
68
Accommodation
2711 Cottages
Lowest Price
CA $222
Highest Price
CA $794

Frequently asked questions

How much do cottages in Windermere cost?
Rates for cottages in Windermere range between CA $222 and CA $794 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.

Explore a world of travel with Expedia