Search Winter Garden Cottages

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Winter Garden cottages

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

Cottage in Winter Garden

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
$455 nightly
The price is $509
Dec 14 - Dec 15
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!
Exterior
The Little Lake Mary Guest House • Warm, Cozy & Inviting

Cottage in Lake Mary

The Little Lake Mary Guest House • Warm, Cozy & Inviting
9.8 out of 10, Exceptional, (43)
"Absolutely perfect location! It was truly one of the best places we have stayed at!"
United States
Jaelyn M.
$245 nightly
The price is $272
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Little Lake Mary Guest House • Warm, Cozy & Inviting
Property grounds
Sweetheart Cottage Near Downtown Lake Mary•Queen Bed, Fire Pit & Private Lanai

Cottage in Lake Mary

Sweetheart Cottage Near Downtown Lake Mary•Queen Bed, Fire Pit & Private Lanai
10.0 out of 10, Exceptional, (17)
"Great place and exactly as described. "
United States
Kanzeda C.
$220 nightly
The price is $243
Dec 14 - Dec 15
Total with taxes and fees
Sweetheart Cottage Near Downtown Lake Mary•Queen Bed, Fire Pit & Private Lanai
Exterior
Orlando Lakefront Tiny House Community

Cottage in Orlando

Orlando Lakefront Tiny House Community
3.0 star property
9.4 out of 10, Exceptional, (331)
"We enjoyed our stay."
United States
Ardeeh
$143 nightly
The price is $161
Dec 14 - Dec 15
Total with taxes and fees
Orlando Lakefront Tiny House Community
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.
$130 nightly
The price is $143
Dec 15 - Dec 16
Total with taxes and fees
Tiny Hidden Cottage
Interior
Downtown Cottage

Cottage in Colonialtown North

Downtown Cottage
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 14 - Dec 15
Total with taxes and fees
Downtown Cottage
Property grounds
Romantic Lakefront Getaway with Balcony Unit A

Cottage in Orlando

Romantic Lakefront Getaway with Balcony Unit A
2.0 star property
$206 nightly
The price is $229
Jan 5 - Jan 6, 2026
Total with taxes and fees
Romantic Lakefront Getaway with Balcony Unit A
Exterior
Incredible Private Lakefront Cottage Retreat

Cottage in Altamonte Springs

Incredible Private Lakefront Cottage Retreat
10.0 out of 10, Exceptional, (29)
"One of our best stays. "
United States
matthew m.
$357 nightly
The price is $395
Dec 15 - Dec 16
Total with taxes and fees
Incredible Private Lakefront Cottage Retreat
Smart TV
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.
$287 nightly
The price is $317
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

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
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.
$293 nightly
The price is $325
Dec 20 - Dec 21
Total with taxes and fees
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Interior
Charming 2-bedroom cottage in Kissimmee

Cottage in Kissimmee

Charming 2-bedroom 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.
$184 nightly
The price is $205
Dec 15 - Dec 16
Total with taxes and fees
Charming 2-bedroom cottage in Kissimmee
Property grounds
Hidden Lake View Cottage 5 miles from Disney!

Cottage in Kissimmee

Hidden Lake View Cottage 5 miles from Disney!
9.0 out of 10, Wonderful, (2)
"Awesome"
United States
Bulmaro S.
$195 nightly
The price is $219
Dec 14 - Dec 15
Total with taxes and fees
Hidden Lake View Cottage 5 miles from Disney!
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
Dec 12 - Dec 13
Total with taxes and fees
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Exterior
Perfect Place for a Perfect Vacation

Cottage in Kissimmee

Perfect Place for a Perfect Vacation
3.0 star property
10.0 out of 10, Exceptional, (1)
$171 nightly
The price is $191
Dec 15 - Dec 16
Total with taxes and fees
Perfect Place for a Perfect Vacation
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.
$155 nightly
The price is $173
Jan 5 - Jan 6, 2026
Total with taxes and fees
Tiny house close to Disney KISSIMMEE
Exterior
Disney, Universal and Legoland Getaway

Cottage in Kissimmee

Disney, Universal and Legoland Getaway
9.2 out of 10, Wonderful, (9)
"I love the place ! It was beautiful! Enough room for everyone "
United States
Anthony M.
$214 nightly
The price is $240
Dec 12 - Dec 13
Total with taxes and fees
Disney, Universal and Legoland Getaway
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 12 - Dec 13
Total with taxes and fees
Cozy Tropical Cottage - 4 mi to Disney
Living area
Cozy Lake Cottage - 4 miles to Disney

Cottage in Kissimmee

Cozy Lake Cottage - 4 miles to Disney
$255 nightly
The price is $285
Dec 20 - Dec 21
Total with taxes and fees
Cozy Lake Cottage - 4 miles to Disney
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.
$187 nightly
The price is $210
Jan 7 - Jan 8, 2026
Total with taxes and fees
Family-Friendly Cottage Near Orlando’s Top Attractions
Exterior
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

Cottage in Kissimmee

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
10.0 out of 10, Exceptional, (2)
"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"
United States
Jennifer b.
$257 nightly
The price is $287
Dec 17 - Dec 18
Total with taxes and fees
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
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 Winter Garden Hotel Reviews

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent
"Yes it was very nice "
Nancy 1-night trip
Posted 1 day ago
Home2 Suites by Hilton Orlando at Flamingo Crossings

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
536
Accommodation
1980 Cottages
Lowest Price
$143
Highest Price
$509

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between $143 and $509 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.

Explore a world of travel with Expedia