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Our top choices for Winter Garden cottages

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
11 Nov - 12 Nov
Fire Pit & Yard: Updated Winter Garden Home!

2. Vacation Village Resort a "Hilltop Haven" Cozy 2-bedroom cottage in Clermont

Vacation Village Resort a "Hilltop Haven" Cozy 2-bedroom cottage in Clermont
Vacation Village
10.0 out of 10, Exceptional, (1 review)
"I loved the home: the views, the sunsets, the lake, the pool, the peace and tranquility, and so much more. Clermont is truly the "Gem of the Hills". And the nearby shops: Publix, Keyfood, the small Brazilian market, Shantee's Caribbean market, etc.; there is such a variety of foods. And Salt Shack overlooking Lake Minneola is another gem. I will be coming again and again to this home and this location."
United States
Anonymous traveller
The price is AU$298
includes taxes & fees
18 Nov - 19 Nov
Vacation Village Resort a "Hilltop Haven" Cozy 2-bedroom cottage in Clermont

3. 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$445
includes taxes & fees
9 Dec - 10 Dec
Shore Steps Cottage - Walking Distance To The Town Of Windermere

4. 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, (70 reviews)
"The Property was very clean ! Super convenient location and the perfect size for a family with 2 younger children ! Suzy was super nice !"
United States
Gary
The price is AU$349
includes taxes & fees
11 Nov - 12 Nov
Orlando Pool Days & Hammock Naps Book Your Escape NOW!

5. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (18 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is AU$254
includes taxes & fees
11 Nov - 12 Nov
Downtown Cottage

6. Charming Historic Cottage with Cozy Porch and Garden Retreat

Charming Historic Cottage with Cozy Porch and Garden Retreat
Polk City
10.0 out of 10, Exceptional, (7 reviews)
"Clean comfort all ok"
United States
Donald P.
The price is AU$297
includes taxes & fees
22 Nov - 23 Nov
Charming Historic Cottage with Cozy Porch and Garden Retreat

7. Family Resort Home w Pool, BBQ & Game Room

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is AU$474
includes taxes & fees
29 Nov - 30 Nov
Family Resort Home w Pool, BBQ & Game Room

8. Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (44 reviews)
"Lovely stay in Mount Dora, perfect location, clean and quiet. Would definitely stay again."
United States
Charlotte
The price is AU$347
includes taxes & fees
11 Nov - 12 Nov
Historic Tremain Cottages

9. 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, (56 reviews)
"Great location, well stocked and beds were very comfortable."
United States
Raegan S.
The price is AU$484
includes taxes & fees
7 Dec - 8 Dec
The Coach House- Entire Home - 2 bedroom/3 bath - Orlando Getaway!

10. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is AU$567
includes taxes & fees
15 Nov - 16 Nov
Serenity - Family & Pet Friendly, Amazing Location

11. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
10.0 out of 10, Exceptional, (1 review)
"Cozy and nice place. It was very clean. Comunication with host was easy. Great view and sitting area from balcony to the lake. Very relaxing!"
United States
jacqueline M.
The price is AU$303
includes taxes & fees
30 Nov - 1 Dec
Romantic Lakefront Getaway with Balcony near Downtown Orlando

12. Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (27 reviews)
"Very nice cottage, beautiful view"
United States
rachel c.
The price is AU$452
includes taxes & fees
29 Nov - 30 Nov
Cozy Lake Front Cottage

13. Cozy 1-bedroom tiny home minutes from Disney, SeaWorld, and Universal!

Cozy 1-bedroom tiny home minutes from Disney, SeaWorld, and Universal!
Kissimmee
Cozy 1-bedroom tiny home minutes from Disney, SeaWorld, and Universal!

14. Golf, Dine & Unwind Poolside! Haines City Getaway

Golf, Dine & Unwind Poolside! Haines City Getaway
3.0 star property
Haines City
The price is AU$620
includes taxes & fees
6 Dec - 7 Dec
Golf, Dine & Unwind Poolside! Haines City Getaway

15. 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$215
includes taxes & fees
12 Nov - 13 Nov
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney

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

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (23 reviews)
"We had an amazing stay! The place was beautiful, cozy, and incredibly comfortable. Even though we had to leave earlier than planned, we truly enjoyed our time here. The host was kind, responsive, and made everything easy from start to finish. We would definitely stay here again and look forward to returning in the future. Highly recommend!"
United States
Chiann M.
The price is AU$360
includes taxes & fees
6 Dec - 7 Dec
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

17. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is AU$358
includes taxes & fees
11 Nov - 12 Nov
Upstay: Bright Family-friendly Retreat With Patio

18. 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, (26 reviews)
"Great stay! Very welcoming home and very comfortable beds. Would rent again."
United States
Thomas K.
The price is AU$358
includes taxes & fees
16 Nov - 17 Nov
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"

19. Newly Remodeled Tiny Home 20 minutes from Disney!~

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
The price is AU$291
includes taxes & fees
11 Nov - 12 Nov
Newly Remodeled Tiny Home 20 minutes from 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

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
275
Accommodation
2858 Cottages
Lowest Price
AU$215
Highest Price
AU$757

Frequently asked questions

How much do cottages in Winter Garden cost?
Rates for cottages in Winter Garden range between AU$215 and AU$757 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.