Search Winter Garden Cottage Rentals from CA $203

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Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

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 CA $250
CA $696 total
includes taxes & fees
May 11 - May 12
Fire Pit & Yard: Updated Winter Garden Home!
Exterior

“Best Stay Ever” – Recent Guest

“Best Stay Ever” – Recent Guest
Lake Mary
9.8 out of 10, Exceptional, (52 reviews)
"Everything was wonderful! We loved the location and the house was cozy and comfortable. "
United States
Mike B.
The price is CA $137
CA $345 total
includes taxes & fees
May 27 - May 28
“Best Stay Ever” – Recent Guest
Terrace/patio

Relax Tonight. Cozy, Quiet and Super Clean.

Relax Tonight. Cozy, Quiet and Super Clean.
Lake Mary
10.0 out of 10, Exceptional, (19 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is CA $123
CA $328 total
includes taxes & fees
May 6 - May 7
Relax Tonight. Cozy, Quiet and Super Clean.
Interior

Downtown Cottage

Downtown Cottage
Colonialtown North
8.2 out of 10, Very good, (11 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is CA $105
CA $262 total
includes taxes & fees
May 11 - May 12
Downtown Cottage
Property grounds

Tiny Hidden Cottage

Tiny Hidden Cottage
Longwood
9.4 out of 10, Exceptional, (66 reviews)
"Great place, found the heater, thank you!Would stay again, just pull the bed away from the wall for us old folk "
United States
Susan J.
The price is CA $102
CA $203 total
includes taxes & fees
May 13 - May 14
Tiny Hidden Cottage
Exterior

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (34 reviews)
"The host was easy to contact and the cottage was very cozy with all necessary amenities. The lakeside location was both beautiful and peaceful, especially considering it is so close to 436 and I4. We definitely plan to return. "
United States
Carol G.
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 CA $142
CA $318 total
includes taxes & fees
May 4 - May 5
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, (37 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 CA $222
CA $455 total
includes taxes & fees
May 4 - May 5
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
House (5 Bedrooms) | Interior

Upstay - Resort Home w Cinema, Pool & Lake View

Upstay - Resort Home w Cinema, Pool & Lake View
3.0 star property
Kissimmee
Upstay - Resort Home w Cinema, Pool & Lake View
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 CA $96
CA $237 total
includes taxes & fees
May 11 - May 12
Tiny house close to Disney KISSIMMEE
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 CA $111
CA $265 total
includes taxes & fees
May 7 - May 8
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 CA $103
CA $389 total
includes taxes & fees
May 1 - May 2
Beautiful Cottage! Your Home Away From Home. 4 miles from 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 CA $123
CA $280 total
includes taxes & fees
May 5 - May 6
Family-Friendly Cottage Near Orlando’s Top Attractions
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 CA $127
CA $302 total
includes taxes & fees
May 4 - May 5
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 CA $97
CA $213 total
includes taxes & fees
May 9 - May 10
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
House (4 Bedrooms) | Interior

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
3.0 star property
Indian Ridge
The price is CA $159
CA $645 total
includes taxes & fees
May 4 - May 5
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Exterior

Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas

Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas
3.5 star property
Reunion
The price is CA $232
CA $858 total
includes taxes & fees
May 13 - May 14
Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas
House (3 Bedrooms) | Living area

Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is CA $151
CA $571 total
includes taxes & fees
May 3 - May 4
Serenity - Family & Pet Friendly, Amazing Location
House (3 Bedrooms) | Interior

Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is CA $144
CA $394 total
includes taxes & fees
May 26 - May 27
Upstay: Bright Family-friendly Retreat With Patio
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)
"Very clean room, quaint, close to the downtown area. "
United States
Raymond
The price is CA $261
CA $290 total
includes taxes & fees
May 11 - May 12
Historic Tremain Cottages
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

Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

10/10 Excellent
"Great service, everything clean , workers professional "
Leonardo D 1-night trip
Posted 1 hour ago
Rosen Inn at Pointe Orlando

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
256
Accommodation
2480 Cottages
Lowest Price
CA $203
Highest Price
CA $858

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between CA $203 and CA $858 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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