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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Winter Garden cottages

Exterior

Cottage in Lake Mary

The Little Lake Mary Guest House • Warm, Cozy & Inviting
9.8 out of 10, Exceptional, (46 reviews)
"Absolutely perfect location! It was truly one of the best places we have stayed at!"
United States
Jaelyn M.
The price is AED 413
AED 984 total
includes taxes & fees
24 Jan - 25 Jan
The Little Lake Mary Guest House • Warm, Cozy & Inviting
Beach

Cottage in Longwood

Tiny Hidden Cottage
9.2 out of 10, Wonderful, (61 reviews)
"Check in process and house were both great. "
United States
Marc H.
The price is AED 290
AED 563 total
includes taxes & fees
28 Jan - 29 Jan
Tiny Hidden Cottage
Interior

Cottage in Colonialtown North

Downtown Cottage
8.6 out of 10, Excellent, (8 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is AED 215
AED 625 total
includes taxes & fees
25 Jan - 26 Jan
Downtown Cottage
Exterior

Cottage in Altamonte Springs

Incredible Private Lakefront Cottage Retreat
10.0 out of 10, Exceptional, (31 reviews)
"One of our best stays. "
United States
matthew m.
The price is AED 522
AED 1,287 total
includes taxes & fees
14 Feb - 15 Feb
Incredible Private Lakefront Cottage Retreat
Exterior

Cottage in College Park

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
10.0 out of 10, Exceptional, (30 reviews)
"Absolutely beautiful place, fully equipped and close to everything. We very much enjoyed our stay."
United States
Sara R.
The price is AED 694
AED 1,293 total
includes taxes & fees
25 Jan - 26 Jan
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Microwave, stovetop

Cottage in Kissimmee

Tiny house close to Disney KISSIMMEE
2.0 star property
8.6 out of 10, Excellent, (4 reviews)
"Just needed a place to stay close to Disney for the night and the place was clean and easy to check in and out. "
United States
Jena B.
The price is AED 294
AED 678 total
includes taxes & fees
13 Feb - 14 Feb
Tiny house close to Disney KISSIMMEE
Dining

Cottage in Kissimmee

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
The price is AED 340
AED 804 total
includes taxes & fees
18 Jan - 19 Jan
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Smart TV, books

Cottage in Kissimmee

Family-Friendly Cottage Near Orlando’s Top Attractions
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.
Family-Friendly Cottage Near Orlando’s Top Attractions
Exterior

Cottage in Kissimmee

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, 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 AED 364
AED 1,026 total
includes taxes & fees
10 Feb - 11 Feb
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Interior

Cottage in Kissimmee

Encore Swanky
3.0 star property
The price is AED 789
AED 2,379 total
includes taxes & fees
1 Feb - 2 Feb
Encore Swanky
House (4 Bedrooms) | Interior

Cottage in Indian Ridge

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
3.0 star property
The price is AED 426
AED 1,732 total
includes taxes & fees
18 Jan - 19 Jan
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Exterior

Cottage in Davenport

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
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 AED 281
AED 594 total
includes taxes & fees
19 Jan - 20 Jan
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Exterior

Cottage in Reunion

Wellerden at Reunion Resort!by Shine Villas
3.5 star property
The price is AED 706
AED 2,401 total
includes taxes & fees
21 Jan - 22 Jan
Wellerden at Reunion Resort!by Shine Villas
The Garden, Pet Friendly | Terrace/patio

Cottage in Mount Dora

Historic Tremain Cottages
3.0 star property
8.6 out of 10, Excellent, (34 reviews)
"Easy check in. Nice, cozy and clean room. Walking distance to all local attractions. Would definitely stay here again. "
United States
Robert
Historic Tremain Cottages
Exterior

Cottage in Kissimmee

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
9.8 out of 10, Exceptional, (7 reviews)
"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.
The price is AED 393
AED 1,061 total
includes taxes & fees
27 Jan - 28 Jan
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Exterior

Cottage in Kissimmee

Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Exterior

Cottage in Kissimmee

Dreamy Coral Cottage with Hot Tub near Disney with Margaritaville Resort &.
2.0 star property
Dreamy Coral Cottage with Hot Tub near Disney with Margaritaville Resort &.
Exterior

Cottage in Kissimmee

Palm Tree Paradise Cottage near Disney with Margaritaville Resort & Island H20.
Palm Tree Paradise Cottage near Disney with Margaritaville Resort & Island H20.
Exterior

Cottage in Kissimmee

Vivid Cottage Near Disney with Margaritaville Resort & Island H2O Access -.
Vivid Cottage Near Disney with Margaritaville Resort & Island H2O Access -.
Exterior

Cottage in Kissimmee

Sky Blue Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Sky Blue 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 Winter Garden Hotel Reviews

Ramada by Wyndham Suites Orlando Airport

Ramada by Wyndham Suites Orlando Airport

10/10 Excellent
"Good breakfast "
Shakia 1-night trip
Posted 13 hours ago
Ramada by Wyndham Suites Orlando Airport

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between AED 563 and AED 2,401 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.

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