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Cottages in Winter Garden

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (330)
"We enjoyed our stay."
Orlando Lakefront Tiny House Community

8000 Lost Shaker Lane

3.0 star property
9.6 out of 10, Exceptional, (7)
"Great place! good location and clean but the patio furniture looked like a hurricane had just happened. I try calling the company incharge of the rental unit but they never came to fix it. Overall good place to stay! "
8000 Lost Shaker Lane

Cozy Cottage 3 blocks from town

10.0 out of 10, Exceptional, (37)
"Great place close to everything would definitely stay again"
Cozy Cottage 3 blocks from town

ADorable Downtown Mount Dora Cottage with Fenced Yard for your pet

9.8 out of 10, Exceptional, (35)
"Great location. "
ADorable Downtown Mount Dora Cottage with Fenced Yard for your pet

Tiny Hidden Cottage

9.2 out of 10, Wonderful, (51)
"We had such a great time staying here. A cute little spot made a great quick stay for us."
$131 nightly
The price is $144
Oct 5 - Oct 6
Total with taxes and fees
Tiny Hidden Cottage

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

10.0 out of 10, Exceptional, (4)
"The cottage was conveniently located near d'town. Comfortable, clean and well-stocked. "
$228 nightly
The price is $250
Oct 6 - Oct 7
Total with taxes and fees
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"

Oaktree Cottage in Mount Dora Historic District

9.8 out of 10, Exceptional, (10)
"Tastefully decorated and well equipped rental. Convenient walk to downtown "
Oaktree Cottage in Mount Dora Historic District

Mount Dora Cottages

3.0 star property
9.4 out of 10, Exceptional, (208)
"Our family loved this place and the neighborhood is perfect for a quiet afternoon. "
$237 nightly
The price is $263
Oct 5 - Oct 6
Total with taxes and fees
Mount Dora Cottages

Family 4BR Home w/ Resort Pool Near Disney

3.0 star property
Family 4BR Home w/ Resort Pool Near Disney

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

10.0 out of 10, Exceptional, (28)
"Easy and convenient in a nice place "
$317 nightly
The price is $352
Oct 6 - Oct 7
Total with taxes and fees
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

5003 Windermere Avenue

3.0 star property
10.0 out of 10, Exceptional, (3)
"Great location, convenient to all shopping needs. Close to Disney World. Good amenities. Great for families traveling together."
5003 Windermere Avenue

LAKEFRONT - kayak, fish, paddleboard, canoe, HOT TUB, golf -near Orlando

10.0 out of 10, Exceptional, (179)
"Had a great time. Very cute home on a relaxing lake. Hosts very helpful and communicative. Wish we could have stayed longer. "
LAKEFRONT - kayak, fish, paddleboard, canoe, HOT TUB, golf -near Orlando

End of the summer special! Guesthouse with lake view and private pool

9.8 out of 10, Exceptional, (42)
"Really happy with our choice to stay here. The house was perfectly clean and comfortable, the kitchen is well equipped, the pool was amazing and felt private and relaxing. This will be my top choice to book again next time I am in the area. "
$243 nightly
The price is $268
Oct 12 - Oct 13
Total with taxes and fees
End of the summer special! Guesthouse with lake view and private pool

High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood

10.0 out of 10, Exceptional, (139)
"Everything was stellar!! Loved Mt Dora!! Loved the location. "
High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood

Charming 2-bedroom cottage in downtown Mount Dora with RV parking, pets welcome

2.0 star property
10.0 out of 10, Exceptional, (15)
"Great place to stay very clean and warm loved it would recommend "
Charming 2-bedroom cottage in downtown Mount Dora with RV parking, pets welcome

Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621

3.0 star property
Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621

Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003

3.0 star property
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003

Downtown Cottage

8.4 out of 10, Very Good, (6)
"Thank you for a wonderful stay. This gem of a guest house is in a perfect location in the Mills50 area of downtown Orlando. A perfectly cozy little home with comfortable beds and a welcoming environment. We look forward to staying again next time we are in Orlando!"
$164 nightly
The price is $181
Oct 12 - Oct 13
Total with taxes and fees
Downtown Cottage

Modern Townhome W/private Pool & Free Water Park!

4.0 star property
8.8 out of 10, Excellent, (5)
"Place was in great location. "
Modern Townhome W/private Pool & Free Water Park!

Historic Tremain Cottages

3.0 star property
8.4 out of 10, Very Good, (31)
"Great location!"
$190 nightly
The price is $211
Oct 8 - Oct 9
Total with taxes and fees
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

Find out more about Winter Garden

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
1,125
Accommodation
2026 Cottages
Lowest Price
$144
Highest Price
$352

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