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Check prices for these dates

In two weeks
19 Sep - 21 Sep
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov

Cottages in Winter Park

Orlando Lakefront Tiny House Community
The Sunshine Lake Shake | 2 bedrooms, individually decorated, individually furnished

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (328)
"We enjoyed our stay."
The price is AED 318
AED 627 total
includes taxes & fees
7 Sep - 8 Sep
Orlando Lakefront Tiny House Community
Tiny Hidden Cottage
Interior

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (50)
"Great location, quiet area & friendly hosts. Could use some updated kitchenware and pans, toaster didnt seem to work. Otherwise was a nice place."
The price is AED 261
AED 531 total
includes taxes & fees
3 Sep - 4 Sep
Tiny Hidden Cottage
LAKEFRONT - kayak, fish, paddleboard, canoe, HOT TUB, golf -near Orlando
Outdoor spa tub

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

10.0 out of 10, Exceptional, (176)
"Very clean, comfortable home with beautiful view of the lake. Enjoyed everything about the stay and will return. Communication was excellent. "
LAKEFRONT - kayak, fish, paddleboard, canoe, HOT TUB, golf -near Orlando
5003 Windermere Avenue
Miscellaneous

5003 Windermere Avenue

3.0 star property
10.0 out of 10, Exceptional, (2)
"Great location, convenient to all shopping needs. Close to Disney World. Good amenities. Great for families traveling together."
5003 Windermere Avenue
Labor Day Getaway!! Guest House with Private pool & WiFi
Exterior

Labor Day Getaway!! Guest House with Private pool & WiFi

9.8 out of 10, Exceptional, (40)
"Wonderful stay. This is my second time here and love the accommodations and location. Very quiet. "
Labor Day Getaway!! Guest House with Private pool & WiFi
~ 12 Mi to Disney: Downtown Winter Garden Cottage!
Exterior

~ 12 Mi to Disney: Downtown Winter Garden Cottage!

9.8 out of 10, Exceptional, (43)
"We LOVE staying at Flamingo House. We are a repeat customer and will be back again soon. Suzie and is wonderful to work with and the house is everything we need!"
~ 12 Mi to Disney: Downtown Winter Garden Cottage!
Private Patio: College Park Cottage in Orlando!
Exterior

Private Patio: College Park Cottage in Orlando!

10.0 out of 10, Exceptional, (8)
"I stayed here for a month with my dog. It was exactly what I needed! The hosts thought of everything that you could possibly need. There is a ton of space and everything is organized and clean. Location is great being close to local shops, necessities, and major roads."
Private Patio: College Park Cottage in Orlando!
Modern Townhome W/private Pool & Free Water Park!
Miscellaneous

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!
Lovely Spacious Guesthouse in Mills 50 District, Orlando
Exterior

Lovely Spacious Guesthouse in Mills 50 District, Orlando

9.0 out of 10, Wonderful, (2)
"Loved this space, by great locations. Can’t wait to visit again."
Lovely Spacious Guesthouse in Mills 50 District, Orlando
2BR COTTAGE IN SANFORD HISTORIC DISTRICT
Exterior

2BR COTTAGE IN SANFORD HISTORIC DISTRICT

10.0 out of 10, Exceptional, (107)
"We had a great time at this charming cottage. Hosts were easy to communicate with and very accommodating. "
2BR COTTAGE IN SANFORD HISTORIC DISTRICT
Orlando Home w/ Private Pool: 10 Mi to UCF Campus!
Exterior

Orlando Home w/ Private Pool: 10 Mi to UCF Campus!

3.0 star property
Orlando Home w/ Private Pool: 10 Mi to UCF Campus!
4718 Sleepy Hollow Drive
House (6 Bedrooms) | Property amenity

4718 Sleepy Hollow Drive

3.0 star property
2.0 out of 10, (1)
"I was highly disappointed after our stay. Our air conditioner never worked and it was inconvenient for our jam packed days to wait for someone to fix this. Really ruined our evenings."
4718 Sleepy Hollow Drive
Downtown Cottage
1 bedroom, desk, iron/ironing board, free WiFi

Downtown Cottage

9.6 out of 10, Exceptional, (4)
"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!"
The price is AED 182
AED 588 total
includes taxes & fees
3 Sep - 4 Sep
Downtown Cottage
10251 Ebb Tide Lane
House (5 Bedrooms) | Property amenity

10251 Ebb Tide Lane

3.0 star property
10251 Ebb Tide Lane
Comfortable 4BR Getaway: Wifi & Parking Included
House (4 Bedrooms) | Front of property

Comfortable 4BR Getaway: Wifi & Parking Included

3.0 star property
Comfortable 4BR Getaway: Wifi & Parking Included
Resort Townhome: Perfect Orlando Vacation Spot!!
House (3 Bedrooms) | Property amenity

Resort Townhome: Perfect Orlando Vacation Spot!!

4.0 star property
8.0 out of 10, Very Good, (1)
Resort Townhome: Perfect Orlando Vacation Spot!!
5014 Tideview Circle #9
House (3 Bedrooms) | Property amenity

5014 Tideview Circle #9

3.0 star property
5014 Tideview Circle #9
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Exterior

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

10.0 out of 10, Exceptional, (26)
"Easy and convenient in a nice place "
The price is AED 658
AED 1,297 total
includes taxes & fees
3 Sep - 4 Sep
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Chic Orlando Family Getaway w/ Fenced Yard!
House (4 Bedrooms) | Interior

Chic Orlando Family Getaway w/ Fenced Yard!

3.0 star property
10.0 out of 10, Exceptional, (1)
Chic Orlando Family Getaway w/ Fenced Yard!
Fire Pit & Yard: Updated Winter Garden Home!
House (2 Bedrooms) | Interior

Fire Pit & Yard: Updated Winter Garden Home!

3.0 star property
Fire Pit & Yard: Updated Winter Garden Home!
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 Park Hotel Reviews

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

10/10 Excellent
"Amazing"
Juan Carlos 2-night trip
Posted 3 days ago
Palazzo Lakeside Hotel
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent
"This resort is a definite stay in the future for me and my family. Great for singles, couples or families with children. If you're not staying with kids & want a quieter experience, don't get a room near the pool or their beautiful waterpark :) "
Jenelle 4-night trip
Posted 3 days ago
Westgate Lakes Resort & Spa Universal Studios Area

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Explore a world of travel with Expedia

Frequently asked questions

How much do cottages in Winter Park cost?
Cottages in Winter Park range between AED 182 and AED 658 per night. These stays offer a chance to touch base 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 Park with Expedia?
Expedia has some terrific cottages in Winter Park, so start packing for a memorable vacation close to nature. If you have a fixed budget, choose how much you'd like to spend and the preferred star rating of your property. Or, make use of our filters to search for cottages with a pool or a kitchen. We'll help you find the perfect fit whatever your plans or bank balance.
How can I find cheap cottages in Winter Park?
Expedia is here to help you easily track down cheap cottages in Winter Park. To discover your dream stay in a couple of quick clicks, simply use our handy filter tool to tailor your search results by amenities, star rating and budget.