Aerial Overlooking Lakeside Homes in Central Florida

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Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

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
$336 nightly
The price is $373
Jun 10 - Jun 11
Total with taxes and fees
Shore Steps Cottage - Walking Distance To The Town Of Windermere
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.
$172 nightly
The price is $190
Jun 10 - Jun 11
Total with taxes and fees
Downtown Cottage
House (4 Bedrooms) | Front of property

Pool Access! Spacious Home Near Wekiwa Springs

Pool Access! Spacious Home Near Wekiwa Springs
3.0 star property
Apopka
$364 nightly
The price is $406
Jun 10 - Jun 11
Total with taxes and fees
Pool Access! Spacious Home Near Wekiwa Springs
Property grounds

Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (22 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
Jun 12 - Jun 13
Total with taxes and fees
Cozy Lake Front Cottage
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.
$153 nightly
The price is $171
Jun 23 - Jun 24
Total with taxes and fees
Tiny house close to Disney KISSIMMEE
Property grounds

Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
$198 nightly
The price is $220
Jun 10 - Jun 11
Total with taxes and fees
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)
$171 nightly
The price is $191
Jun 10 - Jun 11
Total with taxes and fees
Perfect Place for a Perfect Vacation
House (4 Bedrooms) | Interior

Family Resort Home w Pool, BBQ & Game Room

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
$308 nightly
The price is $345
Jun 14 - Jun 15
Total with taxes and fees
Family Resort Home w Pool, BBQ & Game Room
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
10.0 out of 10, Exceptional, (41 reviews)
"Our hosts were incredibly accommodating and welcoming. This was the perfect place for us to stay while in town for a wedding in Winter Park. Thank you! "
United States
Danielle S.
$322 nightly
The price is $358
Jul 2 - Jul 3
Total with taxes and fees
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
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.
$190 nightly
The price is $213
Jun 16 - Jun 17
Total with taxes and fees
Family-Friendly Cottage Near Orlando’s Top Attractions
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
$193 nightly
The price is $216
Jun 27 - Jun 28
Total with taxes and fees
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Exterior

Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney

Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
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.
$141 nightly
The price is $156
Jun 10 - Jun 11
Total with taxes and fees
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
House (3 Bedrooms) | Interior

Davenport Basecamp! 3BR Family Home w/ Patio

Davenport Basecamp! 3BR Family Home w/ Patio
3.0 star property
Davenport
$328 nightly
The price is $364
Jun 10 - Jun 11
Total with taxes and fees
Davenport Basecamp! 3BR Family Home w/ Patio
House (3 Bedrooms) | Interior

Oasis Near Disney w Golf View, Family&pet Friendly

Oasis Near Disney w Golf View, Family&pet Friendly
3.0 star property
Reunion
$424 nightly
The price is $446
Jun 11 - Jun 12
Total with taxes and fees
Oasis Near Disney w Golf View, Family&pet Friendly
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.
$235 nightly
The price is $263
Jun 10 - Jun 11
Total with taxes and fees
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
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.
$250 nightly
The price is $280
Jun 13 - Jun 14
Total with taxes and fees
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
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
$795 nightly
The price is $902
Jun 11 - Jun 12
Total with taxes and fees
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
House (3 Bedrooms) | Interior

Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
$234 nightly
The price is $266
Jun 14 - Jun 15
Total with taxes and fees
Upstay: Bright Family-friendly Retreat With Patio
Property grounds

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
Orlando
$239 nightly
The price is $266
Jul 5 - Jul 6
Total with taxes and fees
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
House (4 Bedrooms) | Interior

~ 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 $472
Jun 10 - Jun 11
Total with taxes and fees
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Everything was good. Very comfortable"
Janellys 1-night trip
Posted 1 hour ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Find out more about Windermere

Windermere Cottages information

Number of reviews
85
Accommodation
2328 Cottages
Lowest Price
$156
Highest Price
$902

Frequently asked questions

How much do cottages in Windermere cost?
Rates for cottages in Windermere range between $156 and $902 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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