A child riding a bicycle on a wooden boardwalk with a body of water and trees in the background.

Search Winter Garden Cottage Accommodations

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Winter Garden cottages

A two-story house with a front porch, a brick driveway, and a well-maintained lawn.

1. Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is AU$727
includes taxes & fees
2 Oct - 3 Oct
Fire Pit & Yard: Updated Winter Garden Home!
A serene landscape with a pond, trees with Spanish moss, and a palm tree.

2. Shore Steps Cottage - Walking Distance To The Town Of Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere
Windermere
10.0 out of 10, Exceptional, (1 review)
The price is AU$509
includes taxes & fees
30 Sept - 1 Oct
Shore Steps Cottage - Walking Distance To The Town Of Windermere
A covered porch with wicker chairs and a ceiling fan.

3. Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (42 reviews)
"Accommodations were comfortable, quaint space. Bed was very comfortable. Just beware the shower is very narrow and ceilings low. Not ideal for a taller or bigger person. Nice and close to the downtown area. Would stay here again."
United States
Betty
The price is AU$259
includes taxes & fees
28 Sept - 29 Sept
Historic Tremain Cottages
A house with a red door, a front porch, and a pathway leading to the entrance.

4. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (15 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is AU$253
includes taxes & fees
27 Sept - 28 Sept
Downtown Cottage
A hammock tied between two wooden posts, a wooden deck, and a view of a lake with trees and a clear sky.

5. Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (25 reviews)
"The setting was very nice and in a quiet area, but conveniently located to travel around Florida. Cottage was clean and very comfortable. Would definitely stay again."
United States
Brenda P.
The price is AU$416
includes taxes & fees
28 Sept - 29 Sept
Cozy Lake Front Cottage
A white building with large windows and a brick pathway leading to it.

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

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
College Park
10.0 out of 10, Exceptional, (52 reviews)
"Everything was super clean and exactly as described. Great location and great stay!"
United States
Garrett S.
The price is AU$453
includes taxes & fees
12 Oct - 13 Oct
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

7. Upstay Family Home w Cinema, Pool & BBQ Clermont

Upstay Family Home w Cinema, Pool & BBQ Clermont
3.0 star property
Clermont
Upstay Family Home w Cinema, Pool & BBQ Clermont
A single-story building with the number 297, a red door, and a bench outside.

8. Orlando Pool Days & Hammock Naps Book Your Escape NOW!

Orlando Pool Days & Hammock Naps Book Your Escape NOW!
Lake Mary
9.8 out of 10, Exceptional, (66 reviews)
"The place was beautiful, cozy and so clean!!!! loved the pool and enjoyed spending my birthday there! will visit again soon!"
United States
Sara L.
The price is AU$359
includes taxes & fees
29 Sept - 30 Sept
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
A patio with outdoor furniture, a wooden deck, and a basketball hoop.

9. Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (21 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is AU$320
includes taxes & fees
28 Sept - 29 Sept
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
A small, single-story house with a gabled roof and a front porch.

10. Mount Dora Cottages

Mount Dora Cottages
3.0 star property
Mount Dora
9.4 out of 10, Exceptional, (212 reviews)
"Perfect spot"
United States
PATRICIA
The price is AU$336
includes taxes & fees
27 Sept - 28 Sept
Mount Dora Cottages
A well-lit garden area with a gravel pathway, decorative lights, and various plants.

11. Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"

Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Mount Dora
10.0 out of 10, Exceptional, (25 reviews)
"Great stay! Very welcoming home and very comfortable beds. Would rent again."
United States
Thomas K.
The price is AU$370
includes taxes & fees
1 Oct - 2 Oct
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
A hallway with a dining area, a black metal chair, and a sign reading "Rendezvous".

12. Beautiful Historic Cottage, Rendezvous

Beautiful Historic Cottage, Rendezvous
Mount Dora
9.4 out of 10, Exceptional, (17 reviews)
"This property is the perfect location for walking downtown shops and dining! "
United States
Julie
The price is AU$282
includes taxes & fees
29 Sept - 30 Sept
Beautiful Historic Cottage, Rendezvous
A single-story house with a front porch, a flag, and a small garden area.

13. Mount Dora Home: Private Pool, Spa & Tropical Bar!

Mount Dora Home: Private Pool, Spa & Tropical Bar!
3.0 star property
Mount Dora
6.0 out of 10, (1 review)
The price is AU$484
includes taxes & fees
28 Sept - 29 Sept
Mount Dora Home: Private Pool, Spa & Tropical Bar!
An aerial view of a resort with multiple swimming pools, a dock, and a residential area with houses.

14. Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
3.0 star property
Kissimmee
The price is AU$1,208
includes taxes & fees
5 Oct - 6 Oct
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
A table with a potted plant and a cup of coffee, overlooking a scenic landscape.

15. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
The price is AU$309
includes taxes & fees
19 Oct - 20 Oct
Romantic Lakefront Getaway with Balcony near Downtown Orlando
A resort with multiple buildings, a central pool area, and a lake.

16. Th60 - 3BR House Near Disney With Pool Access

Th60 - 3BR House Near Disney With Pool Access
3.0 star property
Orlando
The price is AU$664
includes taxes & fees
29 Sept - 30 Sept
Th60 - 3BR House Near Disney With Pool Access
An aerial view of a resort with multiple swimming pools, palm trees, and a golf course.

17. Upstay Disney 5BR Movie Mansionwindsor Cay Resort

Upstay Disney 5BR Movie Mansionwindsor Cay Resort
3.0 star property
Clermont
Upstay Disney 5BR Movie Mansionwindsor Cay Resort
A covered porch with white wicker furniture and green cushions, large windows, and a ceiling fan.

18. Beautiful Historic Cottage, The Garden

Beautiful Historic Cottage, The Garden
Mount Dora
10.0 out of 10, Exceptional, (15 reviews)
"It was a perfect house for our short stay. Great location."
United States
Connie D.
The price is AU$307
includes taxes & fees
28 Sept - 29 Sept
Beautiful Historic Cottage, The Garden
A kitchen with white cabinets, a granite countertop, a stainless steel sink, and a black microwave.

19. Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.4 out of 10, Very good, (9 reviews)
"Proximity to theme parks, restaurants, and shopping"
United States
NOLI
The price is AU$238
includes taxes & fees
26 Sept - 27 Sept
Tiny house close to Disney KISSIMMEE
A small cabin with a porch and a garage, surrounded by trees and a clear sky.

20. Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney

Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
Davenport
6.8 out of 10, (3 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 AU$224
includes taxes & fees
26 Sept - 27 Sept
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min 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.
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

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"So much to do here and see. The property is fantastic and family friendly. We will be back."
DANIEL 2-night trip
Posted 10 hours ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
484
Accommodation
2646 Cottages
Lowest Price
AU$224
Highest Price
AU$1,208

Frequently asked questions

How much do cottages in Winter Garden cost?
Rates for cottages in Winter Garden range between AU$224 and AU$1,208 per night. No matter your budget, you're sure to find a perfect place to reconnect with nature. This price was 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.
What is there to do in Winter Garden near my cottage?
No matter your tastes or interests, Winter Garden has tons to keep you on the move. The Wizarding World of Harry Potter™, Winter Garden Heritage Museum and Garden Theatre are on many travellers' agendas. Don't miss Museum of the Apopkans, The Woods Laser Tag and Carter Family Bowl either. With Expedia's Winter Garden hotel deals, you can discover more fantastic attractions like these with the cash you save.