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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Winter Garden cottages

House (2 Bedrooms) | Interior

Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is ￥28,969
￥80,518 total
includes taxes & fees
Apr 2 - Apr 3
Fire Pit & Yard: Updated Winter Garden Home!
Exterior

Disney Spring Break Stylish Retreat with Private Pool & Magical Night Lights

Disney Spring Break Stylish Retreat with Private Pool & Magical Night Lights
Lake Mary
9.6 out of 10, Exceptional, (49 reviews)
"Absolutely perfect location! It was truly one of the best places we have stayed at!"
United States
Jaelyn M.
The price is ￥17,809
￥41,635 total
includes taxes & fees
Apr 7 - Apr 8
Disney Spring Break Stylish Retreat with Private Pool & Magical Night Lights
Property grounds

Spring Break Special Private Lanai & Outdoor Oasis

Spring Break Special Private Lanai & Outdoor Oasis
Lake Mary
10.0 out of 10, Exceptional, (19 reviews)
"An excellent location for stays in Lake Mary. It has everything a single or a couple needs to feel at home."
United States
Kanzeda C.
The price is ￥14,389
￥37,328 total
includes taxes & fees
Mar 26 - Mar 27
Spring Break Special Private Lanai & Outdoor Oasis
Interior

Downtown Cottage

Downtown Cottage
Colonialtown North
8.0 out of 10, Very Good, (10 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is ￥9,973
￥27,742 total
includes taxes & fees
Mar 29 - Mar 30
Downtown Cottage
Property grounds

Tiny Hidden Cottage

Tiny Hidden Cottage
Longwood
9.4 out of 10, Exceptional, (63 reviews)
"Great little cottage, it was easy to locate and access the property. Nice quiet area and we really enjoyed our stay."
United States
Anna M.
The price is ￥12,506
￥24,265 total
includes taxes & fees
Mar 31 - Apr 1
Tiny Hidden Cottage
Interior

Red Jordan Boho Style Vacation Home

Red Jordan Boho Style Vacation Home
3.0 star property
Meadow Woods
The price is ￥27,093
￥71,925 total
includes taxes & fees
Apr 5 - Apr 6
Red Jordan Boho Style Vacation Home
Exterior

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (33 reviews)
"The host was great! Love the lake and building a fire!"
United States
Rebekah W.
The price is ￥29,919
￥67,227 total
includes taxes & fees
Apr 1 - Apr 2
Incredible Private Lakefront Cottage Retreat
Property grounds

Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
The price is ￥16,424
￥35,933 total
includes taxes & fees
Mar 29 - Mar 30
Romantic Lakefront Getaway with Balcony near Downtown Orlando
Exterior

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
College Park
9.8 out of 10, Exceptional, (35 reviews)
"Lovely spot, in a quiet neighborhood. Clean and spotless, and stocked with amenities for breakfast and snacks. We'll be booking again next time we go down to visit family in Orlando."
United States
John
The price is ￥25,645
￥50,300 total
includes taxes & fees
Mar 30 - Mar 31
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Property grounds

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
Orlando
The price is ￥20,262
￥40,208 total
includes taxes & fees
Mar 31 - Apr 1
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
House (2 Bedrooms) | Interior

Chic Orlando Family Getaway w/ Fenced Yard!

Chic Orlando Family Getaway w/ Fenced Yard!
3.0 star property
Rosemont
10.0 out of 10, Exceptional, (1 review)
The price is ￥21,582
￥83,246 total
includes taxes & fees
Apr 9 - Apr 10
Chic Orlando Family Getaway w/ Fenced Yard!
Microwave, stovetop

Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.4 out of 10, Very Good, (6 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 ￥12,506
￥29,039 total
includes taxes & fees
Apr 13 - Apr 14
Tiny house close to Disney KISSIMMEE
Smart TV, books

Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions
Kissimmee
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.
The price is ￥15,355
￥33,172 total
includes taxes & fees
Apr 21 - Apr 22
Family-Friendly Cottage Near Orlando’s Top Attractions
Exterior

Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is ￥13,282
￥30,857 total
includes taxes & fees
Apr 8 - Apr 9
Perfect Place for a Perfect Vacation
Exterior

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
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 ￥15,672
￥44,204 total
includes taxes & fees
Apr 13 - Apr 14
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Dining

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Kissimmee
The price is ￥14,674
￥34,352 total
includes taxes & fees
Mar 29 - Mar 30
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Exterior

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Davenport
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 ￥15,672
￥29,583 total
includes taxes & fees
Mar 26 - Mar 27
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Interior

Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is ￥21,899
￥71,933 total
includes taxes & fees
Mar 26 - Mar 27
Serenity - Family & Pet Friendly, Amazing Location
The Garden, Pet Friendly | Terrace/patio

Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (37 reviews)
"The room was clean and the location is perfect. The host was available and very accommodating. "
United States
Kimberly
Historic Tremain Cottages
Exterior

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.6 out of 10, Exceptional, (8 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
The price is ￥18,424
￥46,652 total
includes taxes & fees
Apr 6 - Apr 7
"Casa Kiwi" Margaritaville Cottage 5 minutes 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

Marriott's Grande Vista

Marriott's Grande Vista

10/10 Excellent
"My room was nice and clean and the kids loved watching March Madness on the large screen in the pool area "
Jaskern 2-night trip
Posted 1 hour ago
Marriott's Grande Vista

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
167
Accommodation
1982 Cottages
Lowest Price
￥24,265
Highest Price
￥83,246

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between ￥24,265 and ￥83,246 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.