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Cottages in Winter Garden

House (2 Bedrooms) | Interior
Fire Pit & Yard: Updated Winter Garden Home!

Cottage in Winter Garden

3.0 star property
$455 nightly
The price is $509
Nov 29 - Nov 30
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!
The Sunshine Lake Shake | Individually decorated, individually furnished, laptop workspace
Orlando Lakefront Tiny House Community

Cottage in Orlando

3.0 star property
9.4 out of 10, Exceptional, (331)
"We enjoyed our stay."
United States
Ardeeh
$151 nightly
The price is $169
Dec 7 - Dec 8
Total with taxes and fees
Orlando Lakefront Tiny House Community
Exterior
The Little Lake Mary Guest House • Warm, Cozy & Inviting

Cottage in Lake Mary

9.8 out of 10, Exceptional, (43)
"Absolutely incredible house, felt like home away from home"
United States
Hannah R.
$240 nightly
The price is $265
Dec 7 - Dec 8
Total with taxes and fees
The Little Lake Mary Guest House • Warm, Cozy & Inviting
Interior
Tiny Hidden Cottage

Cottage in Longwood

9.2 out of 10, Wonderful, (56)
"Check in process and house were both great. "
United States
Marc H.
$131 nightly
The price is $144
Nov 29 - Nov 30
Total with taxes and fees
Tiny Hidden Cottage
Property grounds
Sweetheart Cottage Near Downtown Lake Mary•Queen Bed, Fire Pit & Private Lanai

Cottage in Lake Mary

10.0 out of 10, Exceptional, (16)
"Great place and exactly as described. "
United States
Kanzeda C.
$234 nightly
The price is $259
Dec 14 - Dec 15
Total with taxes and fees
Sweetheart Cottage Near Downtown Lake Mary•Queen Bed, Fire Pit & Private Lanai
Exterior
Charming 2-bedroom Country Cottage in Kissimmee with private parking

Cottage in Kissimmee

9.0 out of 10, Wonderful, (4)
"great experience. very clean and in a good area"
United States
Aubrey V.
$120 nightly
The price is $133
Dec 15 - Dec 16
Total with taxes and fees
Charming 2-bedroom Country Cottage in Kissimmee with private parking
Exterior
Incredible Private Lakefront Cottage Retreat

Cottage in Altamonte Springs

10.0 out of 10, Exceptional, (27)
"One of our best stays. "
United States
matthew m.
$284 nightly
The price is $314
Dec 12 - Dec 13
Total with taxes and fees
Incredible Private Lakefront Cottage Retreat
1 bedroom, desk, iron/ironing board, free WiFi
Downtown Cottage

Cottage in Colonialtown North

8.4 out of 10, Very Good, (6)
"Thank you for a wonderful stay. This gem of a guest house is in a perfect location in the Mills50 area of downtown Orlando. A perfectly cozy little home with comfortable beds and a welcoming environment. We look forward to staying again next time we are in Orlando!"
United States
Josh L.
$149 nightly
The price is $165
Dec 2 - Dec 3
Total with taxes and fees
Downtown Cottage
Fridge, microwave, oven, stovetop
Garden Cottage-Swim/Spa sleeps 6 Ctrl Orlando Disney Universal SeaWorld Beaches,

Cottage in Altamonte Springs

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.
$280 nightly
The price is $310
Dec 22 - Dec 23
Total with taxes and fees
Garden Cottage-Swim/Spa sleeps 6 Ctrl Orlando Disney Universal SeaWorld Beaches,
Exterior
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

Cottage in College Park

10.0 out of 10, Exceptional, (29)
"Absolutely beautiful place, fully equipped and close to everything. We very much enjoyed our stay."
United States
Sara R.
$336 nightly
The price is $373
Nov 29 - Nov 30
Total with taxes and fees
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Children's area
Charming 2-bedroom cottage in Kissimmee

Cottage in Kissimmee

2.0 star property
10.0 out of 10, Exceptional, (1)
"Kudos to the hosts. A seamless experience. My first ever vacation rental and I was very impressed. The cottage was super clean and was equipped with everything and then some. "
United States
Gail E.
$197 nightly
The price is $221
Nov 30 - Dec 1
Total with taxes and fees
Charming 2-bedroom cottage in Kissimmee
Property grounds
Hidden Lake View Cottage 5 miles from Disney!

Cottage in Kissimmee

9.0 out of 10, Wonderful, (2)
"Awesome"
United States
Bulmaro S.
$198 nightly
The price is $222
Dec 1 - Dec 2
Total with taxes and fees
Hidden Lake View Cottage 5 miles from Disney!
Microwave, stovetop
Tiny house close to Disney KISSIMMEE

Cottage in 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.
$155 nightly
The price is $173
Dec 7 - Dec 8
Total with taxes and fees
Tiny house close to Disney KISSIMMEE
Property grounds
Fully-Stocked Cozy Tropical Cottage-4 mi to Disney

Cottage in Kissimmee

$237 nightly
The price is $264
Dec 3 - Dec 4
Total with taxes and fees
Fully-Stocked Cozy Tropical Cottage-4 mi to Disney
Exterior
Perfect Place for a Perfect Vacation

Cottage in Kissimmee

3.0 star property
10.0 out of 10, Exceptional, (1)
$172 nightly
The price is $192
Dec 5 - Dec 6
Total with taxes and fees
Perfect Place for a Perfect Vacation
Front of property
Historic Tremain Cottages

Cottage in Mount Dora

3.0 star property
8.4 out of 10, Very Good, (32)
"Great location!"
United States
Lisa
$188 nightly
The price is $209
Dec 29 - Dec 30
Total with taxes and fees
Historic Tremain Cottages
Private kitchen
Cozy Lake Cottage - 4 miles to Disney

Cottage in Kissimmee

$247 nightly
The price is $277
Dec 20 - Dec 21
Total with taxes and fees
Cozy Lake Cottage - 4 miles to Disney
Property grounds
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

Cottage in Kissimmee

$189 nightly
The price is $212
Nov 30 - Dec 1
Total with taxes and fees
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Exterior
Disney, Universal and Legoland Getaway

Cottage in Kissimmee

9.2 out of 10, Wonderful, (9)
"I love the place ! It was beautiful! Enough room for everyone "
United States
Anthony M.
$218 nightly
The price is $244
Nov 29 - Nov 30
Total with taxes and fees
Disney, Universal and Legoland Getaway
House (4 Bedrooms) | Interior
Family-friendly Home w/ Lanai ~ 6 Mi to Disney

Cottage in Montego Bay

3.0 star property
$474 nightly
The price is $534
Nov 29 - Nov 30
Total with taxes and fees
Family-friendly Home w/ Lanai ~ 6 Mi to Disney
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 Winter Garden Hotel Reviews

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Room was spotless & staff was super courteous."
Cesar 2-night trip
Posted 15 hours ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Find out more about Winter Garden

Winter Garden Cottages information

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Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between and per night. These stays offer a chance to get reacquainted with nature — at a price you can afford. 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.
Why book your cottage in Winter Garden with Expedia?
Expedia has some great cottages in Winter Garden, so get ready for a memorable vacation on nature's doorstep. If you're sticking to a budget, select how much you'd like to spend and the preferred star rating of your property. Or, use our filters to search for cottages with free WiFi or a kitchen. We'll help you find the right fit whatever your bank balance or plans.
How can I find cheap cottages in Winter Garden?
With Expedia's convenient filter tool, scoring cheap cottages in Winter Garden has never been simpler. To discover accommodations that'll make your wallet happy, fine-tune your search results by budget, star rating and amenities.
What is there to do in Winter Garden near my cottage?
Whatever you're into, Winter Garden has plenty of things to keep you on the go. Orange County National Golf Club, Resurrection Catholic Church and West Orange Trail are on many travelers' agendas. Don't forget to explore Winter Garden Art Association, Winter Garden Heritage Museum and Oakland Nature Preserve either. With Expedia's Winter Garden hotel deals, you'll be able to see more renowned attractions like these with the cash you save.

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