Search Windermere Cottage Rentals from CA $214

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Windermere cottages

Property grounds

Shore Steps Cottage - Walking Distance To The Town Of Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere
Windermere
The price is CA $184
CA $493 total
includes taxes & fees
May 22 - May 23
Shore Steps Cottage - Walking Distance To The Town Of Windermere
Property grounds

Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (22 reviews)
"Host was very accommodating and the cottage was perfect"
United States
Ashley P.
The price is CA $184
CA $403 total
includes taxes & fees
May 22 - May 23
Cozy Lake Front Cottage
Exterior

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (36 reviews)
"The host was easy to contact and the cottage was very cozy with all necessary amenities. The lakeside location was both beautiful and peaceful, especially considering it is so close to 436 and I4. We definitely plan to return. "
United States
Carol G.
The price is CA $184
CA $494 total
includes taxes & fees
May 26 - May 27
Incredible Private Lakefront Cottage Retreat
Interior

Downtown Cottage

Downtown Cottage
Colonialtown North
8.2 out of 10, Very good, (11 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is CA $105
CA $263 total
includes taxes & fees
Jun 1 - Jun 2
Downtown Cottage
House (2 Bedrooms) | Interior

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 $187
CA $721 total
includes taxes & fees
Jun 8 - Jun 9
Chic Orlando Family Getaway w/ Fenced Yard!
Microwave, stovetop

Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.4 out of 10, Very good, (7 reviews)
"Nice, Cute little place"
United States
Brenda N.
The price is CA $95
CA $237 total
includes taxes & fees
May 25 - May 26
Tiny house close to Disney KISSIMMEE
Exterior

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
College Park
9.8 out of 10, Exceptional, (37 reviews)
"Lovely spot, in a quiet neighborhood. Clean and spotless, and stocked with amenities for breakfast and snacks. We'll be booking again next time we go down to visit family in Orlando."
United States
John
The price is CA $247
CA $492 total
includes taxes & fees
Jun 15 - Jun 16
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Interior

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 $143
CA $451 total
includes taxes & fees
May 26 - May 27
Family Resort Home w Pool, BBQ & Game Room
Property grounds

Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
The price is CA $135
CA $308 total
includes taxes & fees
Jun 1 - Jun 2
Romantic Lakefront Getaway with Balcony near Downtown Orlando
Exterior

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 $111
CA $266 total
includes taxes & fees
May 25 - May 26
Perfect Place for a Perfect Vacation
House (3 Bedrooms) | Interior

Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is CA $113
CA $529 total
includes taxes & fees
May 26 - May 27
Serenity - Family & Pet Friendly, Amazing Location
Smart TV, books

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 $124
CA $281 total
includes taxes & fees
May 25 - May 26
Family-Friendly Cottage Near Orlando’s Top Attractions
Exterior

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 $122
CA $418 total
includes taxes & fees
Jun 10 - Jun 11
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Exterior

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.6 out of 10, Exceptional, (10 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
The price is CA $150
CA $401 total
includes taxes & fees
Jun 8 - Jun 9
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Interior

Pool Access! Spacious Home Near Wekiwa Springs

Pool Access! Spacious Home Near Wekiwa Springs
3.0 star property
Apopka
The price is CA $186
CA $559 total
includes taxes & fees
Jun 8 - Jun 9
Pool Access! Spacious Home Near Wekiwa Springs
Dining

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 $127
CA $301 total
includes taxes & fees
Jun 1 - Jun 2
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Exterior

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
The price is CA $248
CA $1,181 total
includes taxes & fees
Jun 3 - Jun 4
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
House (5 Bedrooms) | Interior

Family-friendly Villa w Pool, Hot Tub & Games Room

Family-friendly Villa w Pool, Hot Tub & Games Room
3.0 star property
Kissimmee
Family-friendly Villa w Pool, Hot Tub & Games Room
Exterior

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
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.
The price is CA $98
CA $214 total
includes taxes & fees
May 22 - May 23
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Property grounds

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
Orlando
The price is CA $166
CA $351 total
includes taxes & fees
Jun 2 - Jun 3
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
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

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

10/10 Excellent
"We came to pivot our lodging from a bad lodging solution at the last minute (at ) and that was a blessing in disguise! Our whole family loved our stay here. Clean, great environment, kind and helpful staff, great price, ate the breakfast and swam in the pool with my daughter every day. Next time we come to Orlando we will look for this hotel right away!"
Parker 4-night trip
Posted 1 hour ago
Kompose Boutique Resort at Theme Parks

Find out more about Windermere

Windermere Cottages information

Number of reviews
119
Accommodation
2269 Cottages
Lowest Price
CA $214
Highest Price
CA $1,181

Frequently asked questions

How much do cottages in Windermere cost?
Rates for cottages in Windermere range between CA $214 and CA $1,181 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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