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Check prices for these dates

Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan
In one month
6 Feb - 8 Feb
In two months
6 Mar - 8 Mar

Our top choices for Winter Garden cottages

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, (44)
"Absolutely perfect location! It was truly one of the best places we have stayed at!"
United States
Jaelyn M.
The price is AED 459
AED 1,021 total
includes taxes & fees
24 Jan - 25 Jan
The Little Lake Mary Guest House • Warm, Cozy & Inviting
Interior
Tiny Hidden Cottage

Cottage in Longwood

Tiny Hidden Cottage
9.2 out of 10, Wonderful, (60)
"Check in process and house were both great. "
United States
Marc H.
The price is AED 290
AED 563 total
includes taxes & fees
12 Jan - 13 Jan
Tiny Hidden Cottage
1 bedroom, desk, iron/ironing board, free WiFi
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.
The price is AED 182
AED 588 total
includes taxes & fees
8 Jan - 9 Jan
Downtown Cottage
Exterior
Incredible Private Lakefront Cottage Retreat

Cottage in Altamonte Springs

Incredible Private Lakefront Cottage Retreat
10.0 out of 10, Exceptional, (31)
"One of our best stays. "
United States
matthew m.
The price is AED 423
AED 1,195 total
includes taxes & fees
8 Jan - 9 Jan
Incredible Private Lakefront Cottage Retreat
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, (18)
"Lots of room to spend time with family and friends. Great location, easy to move around Orlando from here."
United States
Rachael C.
The price is AED 503
AED 1,151 total
includes taxes & fees
13 Jan - 14 Jan
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, (30)
"Absolutely beautiful place, fully equipped and close to everything. We very much enjoyed our stay."
United States
Sara R.
The price is AED 744
AED 1,356 total
includes taxes & fees
8 Jan - 9 Jan
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
The price is AED 375
AED 1,046 total
includes taxes & fees
19 Jan - 20 Jan
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
8.6 out of 10, Excellent, (4)
"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
12 Jan - 13 Jan
Tiny house close to Disney KISSIMMEE
Property grounds
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
The price is AED 324
AED 778 total
includes taxes & fees
7 Jan - 8 Jan
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Interior
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.
The price is AED 331
AED 740 total
includes taxes & fees
7 Jan - 8 Jan
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.
The price is AED 474
AED 1,187 total
includes taxes & fees
31 Jan - 1 Feb
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Interior
Watersong Swanky

Cottage in Davenport

Watersong Swanky
3.0 star property
The price is AED 1,244
AED 3,693 total
includes taxes & fees
8 Jan - 9 Jan
Watersong Swanky
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
The price is AED 426
AED 1,732 total
includes taxes & fees
10 Jan - 11 Jan
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
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.
The price is AED 294
AED 609 total
includes taxes & fees
7 Jan - 8 Jan
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Front of property
Historic Tremain Cottages

Cottage in Mount Dora

Historic Tremain Cottages
3.0 star property
8.6 out of 10, Excellent, (34)
"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
Property grounds
Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.

Cottage in Kissimmee

Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.
Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.
House (4 Bedrooms) | Interior
Upstay: Pet-friendly Family Home w Pool & Sundeck

Cottage in Kissimmee

Upstay: Pet-friendly Family Home w Pool & Sundeck
3.0 star property
The price is AED 342
AED 1,168 total
includes taxes & fees
7 Jan - 8 Jan
Upstay: Pet-friendly Family Home w Pool & Sundeck
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, (7)
"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 360
AED 1,023 total
includes taxes & fees
12 Jan - 13 Jan
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Exterior
Dreamy Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.

Cottage in Kissimmee

Dreamy Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
Dreamy Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
Exterior
The Pearl Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.

Cottage in Kissimmee

The Pearl Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
The Pearl Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
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

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent
"Breakfast ended at 9, should have ended at 10 too short time and too many people Ran out of utensils and glassware Too long lines in queue with not enough seating space"
Marlene 3-night trip
Posted 8 hours ago
Home2 Suites by Hilton Orlando at Flamingo Crossings

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between AED 563 and AED 3,693 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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