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Our top choices for Windermere cottages

Interior
Downtown Cottage

Cottage in Colonialtown North

Downtown Cottage
8.4 out of 10, Very Good, (7)
"Clean perfect location for what we needed "
United States
Jerred B.
$154 nightly
The price is $170
Jan 1 - Jan 2, 2026
Total with taxes and fees
Downtown Cottage
Beach
Tiny Hidden Cottage

Cottage in Longwood

Tiny Hidden Cottage
9.2 out of 10, Wonderful, (58)
"Check in process and house were both great. "
United States
Marc H.
$131 nightly
The price is $144
Dec 24 - Dec 25
Total with taxes and fees
Tiny Hidden Cottage
Exterior
Garden Cottage-Swim/Spa sleeps 6 Ctrl Orlando Disney Universal SeaWorld Beaches,

Cottage in Altamonte Springs

Garden Cottage-Swim/Spa sleeps 6 Ctrl Orlando Disney Universal SeaWorld Beaches,
8.6 out of 10, Excellent, (17)
"Lots of room to spend time with family and friends. Great location, easy to move around Orlando from here."
United States
Rachael C.
$283 nightly
The price is $313
Jan 13 - Jan 14, 2026
Total with taxes and fees
Garden Cottage-Swim/Spa sleeps 6 Ctrl Orlando Disney Universal SeaWorld Beaches,
Exterior
Incredible Private Lakefront Cottage Retreat

Cottage in Altamonte Springs

Incredible Private Lakefront Cottage Retreat
10.0 out of 10, Exceptional, (30)
"One of our best stays. "
United States
matthew m.
$355 nightly
The price is $393
Jan 8 - Jan 9, 2026
Total with taxes and fees
Incredible Private Lakefront Cottage Retreat
Exterior
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

Cottage in College Park

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
10.0 out of 10, Exceptional, (30)
"Absolutely beautiful place, fully equipped and close to everything. We very much enjoyed our stay."
United States
Sara R.
$319 nightly
The price is $355
Jan 23 - Jan 24, 2026
Total with taxes and fees
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
House (3 Bedrooms) | Interior
Upstay: Bright Family-friendly Retreat With Patio

Cottage in Chatham Park

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
$239 nightly
The price is $271
Jan 8 - Jan 9, 2026
Total with taxes and fees
Upstay: Bright Family-friendly Retreat With Patio
Microwave, stovetop
Tiny house close to Disney KISSIMMEE

Cottage in Kissimmee

Tiny house close to Disney KISSIMMEE
2.0 star property
9.0 out of 10, Wonderful, (2)
"The location was great. We really just needed somewhere to sleep because we spent the day at the Disney Parks. The place had enough beds and was a great price."
United States
Christine M.
$158 nightly
The price is $177
Jan 6 - Jan 7, 2026
Total with taxes and fees
Tiny house close to Disney KISSIMMEE
Exterior
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema

Cottage in Kissimmee

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
3.0 star property
$1,060 nightly
The price is $1,203
Dec 29 - Dec 30
Total with taxes and fees
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
Smart TV, books
Family-Friendly Cottage Near Orlando’s Top Attractions

Cottage in Kissimmee

Family-Friendly Cottage Near Orlando’s Top Attractions
10.0 out of 10, Exceptional, (1)
"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.
$180 nightly
The price is $202
Jan 7 - Jan 8, 2026
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

Cottage in Kissimmee

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
$188 nightly
The price is $211
Jan 5 - Jan 6, 2026
Total with taxes and fees
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Exterior
Charming 1-bedroom cottage in Kissimmee

Cottage in Kissimmee

Charming 1-bedroom cottage in Kissimmee
$222 nightly
The price is $249
Dec 29 - Dec 30
Total with taxes and fees
Charming 1-bedroom cottage in Kissimmee
Living area
Cozy Lake Cottage - 4 miles to Disney

Cottage in Kissimmee

Cozy Lake Cottage - 4 miles to Disney
$253 nightly
The price is $283
Dec 24 - Dec 25
Total with taxes and fees
Cozy Lake Cottage - 4 miles to Disney
Private kitchen
Cozy Tropical Cottage - 4 mi to Disney

Cottage in Kissimmee

Cozy Tropical Cottage - 4 mi to Disney
$255 nightly
The price is $285
Dec 28 - Dec 29
Total with taxes and fees
Cozy Tropical Cottage - 4 mi to Disney
House (Multiple Bedrooms) | Interior
Watersong Swanky

Cottage in Davenport

Watersong Swanky
3.0 star property
$899 nightly
The price is $1,005
Jan 8 - Jan 9, 2026
Total with taxes and fees
Watersong Swanky
Exterior
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD

Cottage in Davenport

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
5.0 out of 10, (2)
"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.
$150 nightly
The price is $166
Dec 28 - Dec 29
Total with taxes and fees
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
House (6 Bedrooms) | Interior
Upstay: 6BR Resort Home w Pool & Basketball Court

Cottage in Kissimmee

Upstay: 6BR Resort Home w Pool & Basketball Court
3.0 star property
Upstay: 6BR Resort Home w Pool & Basketball Court
House (4 Bedrooms) | Interior
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

Cottage in Indian Ridge

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
3.0 star property
$419 nightly
The price is $472
Jan 10 - Jan 11, 2026
Total with taxes and fees
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Exterior
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

Cottage in Kissimmee

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
9.8 out of 10, Exceptional, (6)
"Wonderful place to stay overnight. Nice furnishings. Good room layout for family. Convenience of washer and dryer. Host was quick and responsive. Thank you for a terrific stay."
United States
George L.
$268 nightly
The price is $300
Jan 7 - Jan 8, 2026
Total with taxes and fees
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Exterior
Sunrise Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.

Cottage in Kissimmee

Sunrise Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
10.0 out of 10, Exceptional, (1)
"Comfy, cozy and room for everyone to have their own space . Easy to get around. Places to eat and shop right outside the property, so convenient."
United States
Marilou J.
Sunrise Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
Exterior
Celestial Cottage near Disney with Margaritaville Resort & Island H2O Access -.

Cottage in Kissimmee

Celestial Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Celestial Cottage near Disney with Margaritaville Resort & Island H2O Access -.
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 Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"Yes"
Khadine 1-night trip
Posted 16 hours ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Find out more about Windermere

Windermere Cottages information

Number of reviews
137
Accommodation
1829 Cottages
Lowest Price
$144
Highest Price
$1,203

Frequently asked questions

How much do cottages in Windermere cost?
Rates for cottages in Windermere range between $144 and $1,203 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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