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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

Compare 202 Cottages in Winter Park with updated reviews, rates, and availability.

Orlando Lakefront Tiny House Community
Exterior

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (253)
"They went the extra mile to make me comfortable. It's really great here. Lots of nature but downtown is close by. "
The price is AED 219
AED 515 total
includes taxes & fees
12 Feb - 13 Feb
Orlando Lakefront Tiny House Community
Tiny Hidden Cottage
Room

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (28)
"The house is perfect for my weekend trips to the area and I plan to stay there again if my travels permit. "
The price is AED 298
AED 571 total
includes taxes & fees
11 Feb - 12 Feb
Tiny Hidden Cottage
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Orlando oasis ☀️

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

9.8 out of 10, Exceptional, (9)
"It's a lovely, well-appointed, well-located place. The cottage is within easy walking distance of multiple restaurants. The communication was excellent. I hope to stay at the cottage again soon!"
The price is AED 477
AED 1,039 total
includes taxes & fees
26 Jan - 27 Jan
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
The Sanford Foodie Guest House
Terrace/patio

The Sanford Foodie Guest House

9.8 out of 10, Exceptional, (6)
"Great spot if you are visiting the area. The host was nice and helpful!"
The price is AED 239
AED 748 total
includes taxes & fees
26 Jan - 27 Jan
The Sanford Foodie Guest House
Florida Valentine’s Day Guest House with Private pool & WiFi
Miscellaneous

Florida Valentine’s Day Guest House with Private pool & WiFi

9.8 out of 10, Exceptional, (27)
"I had surgery and stayed here for my recovery, nice quiet area, easily accessible to stores and very comfortable bed. I felt very comfortable while recuperating. Washer and dryer big plus and the pool was beautiful and well kept. I didn't get to use the pool but I sure would have loved to. I will be back when I have to go for my checkups "
Florida Valentine’s Day Guest House with Private pool & WiFi
Dtwn Winter Garden Home: 12 Mi to Disney!
Winter Garden Vacation Rental | 3BR | 2BA | 1,200 Sq Ft | 3 Steps to Enter

Dtwn Winter Garden Home: 12 Mi to Disney!

9.6 out of 10, Exceptional, (5)
"We evacuated from Helene. Because we were unable to return to our home, we ended up having to rent multiple vacation rentals. This is the first home that actually looked like it did online--really lovely. (I agree, yard can use some TLC) I liked the retro touches throughout. Comfortable furniture and beds. Luxury towels and linens. Really nice! Walk west and cross over Dillard two block then three blocks north to Plant street and you'll find many wonderful restaurants and shops. Saturday...
Dtwn Winter Garden Home: 12 Mi to Disney!
Stunning Lakeview Townhome w/ Private Pool!
Pool

Stunning Lakeview Townhome w/ Private Pool!

4.0 star property
8.4 out of 10, Very Good, (9)
"Perfect location house was just what is described "
Stunning Lakeview Townhome w/ Private Pool!
Orlando Home w/ Private Pool: 10 Mi to UCF Campus!
Pool

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

3.0 star property
Orlando Home w/ Private Pool: 10 Mi to UCF Campus!
Valentine’s Day Cottage with queen bed & fire pit.
Room

Valentine’s Day Cottage with queen bed & fire pit.

10.0 out of 10, Exceptional, (10)
"This cozy cottage was just as described. Tucked away on a quiet street and just perfect for our getaway. Communication with host was prompt and precise. The place was very clean and offered all amenities that you would need to fill right at home would definitely recommend."
The price is AED 386
AED 896 total
includes taxes & fees
17 Feb - 18 Feb
Valentine’s Day Cottage with queen bed & fire pit.
16 Mi to Disney: Cottage w/ Deck in Winter Garden
Living area

16 Mi to Disney: Cottage w/ Deck in Winter Garden

3.0 star property
10.0 out of 10, Exceptional, (1)
"This house is adorable! It was perfect for us as a couple. Very sweetly decorated and homey. The neighborhood is very quiet and off the beaten path, as they say, yet very close to stores and beautiful downtown Winter Garden. We would SO stay again! Would love to do a seasonal stay. "
16 Mi to Disney: Cottage w/ Deck in Winter Garden
The Pink Door Cottage-Historic Sanford
Exterior detail

The Pink Door Cottage-Historic Sanford

10.0 out of 10, Exceptional, (11)
"Super clean, comfortable home within walking distance to Sanford downtown. You’re right smack in the middle of the historic district if you stay on this charming home. We walked everywhere and really enjoyed the location. The house as well had everything you’d need. "
The Pink Door Cottage-Historic Sanford
Lake-view Home w/ Game Room in Orlando!
Exterior

Lake-view Home w/ Game Room in Orlando!

3.0 star property
Lake-view Home w/ Game Room in Orlando!
Caribbean Dreamin
Living area

Caribbean Dreamin

3.0 star property
10.0 out of 10, Exceptional, (1)
"This Caribbean Dreamin property is awesome! It is clean, spacious, and very well kept. Contrary to the contract, the house includes all the amenities for all bathrooms as well as dishwashing detergent. Nice touch! The community is very pretty and well kept. Shopping nearby. Unfortunately, we were here for a couple nights during Hurricane Milton so didn't go out at all. But being in a nice home away from home made a difference during the stressful time. I would highly recommend this...
Caribbean Dreamin
Luxurious Home W/private Pool, Near Disney!
Pool

Luxurious Home W/private Pool, Near Disney!

4.0 star property
8.0 out of 10, Very Good, (3)
"House was great, however chose to pay for the early check-in so we could use the pool. To use the heater for the pool it’s an up charge. Understand. However they charged me $25 per day for the entire stay but the pool wasn’t warm until the morning we checked out."
Luxurious Home W/private Pool, Near Disney!
5003 Windermere Avenue
Pool

5003 Windermere Avenue

3.0 star property
10.0 out of 10, Exceptional, (1)
"very nice house , with 4 Rooms , 1 of them in the 1st floor so very convenient to my mom . kitchen is awesome , new and good quality appliances we take the kids to the club , there is a lazy river and the sliders are fun . No additional charges . "
5003 Windermere Avenue
Screened Lanai + Fenced Yard: Luxe Orlando Home
Living area

Screened Lanai + Fenced Yard: Luxe Orlando Home

3.0 star property
Screened Lanai + Fenced Yard: Luxe Orlando Home
Downtown Cottage
Exterior detail

Downtown Cottage

10.0 out of 10, Exceptional, (3)
"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 349
AED 776 total
includes taxes & fees
26 Jan - 27 Jan
Downtown Cottage
THE HIDEAWAY AT COLLEGE PARK
Property grounds

THE HIDEAWAY AT COLLEGE PARK

8.0 out of 10, Very Good, (1)
"Overall, this was a great stay for my needs. The location was close to where I needed to be. I ABSOLUTELY loved the decor. I had three concerns. We did not know how to use the security code and had to YouTube directions. The second bedroom did not have a "bed" and there is not a curtain so my guest slept in the living room. bedro a bedroom and was very small"
THE HIDEAWAY AT COLLEGE PARK
Beautiful, Modern Home W/private Pool! Near WDW
Living area

Beautiful, Modern Home W/private Pool! Near WDW

4.0 star property
8.4 out of 10, Very Good, (12)
"It was a nice place ."
Beautiful, Modern Home W/private Pool! Near WDW
Premier Lakeview Stylish Home
Room

Premier Lakeview Stylish Home

Premier Lakeview Stylish 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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Other property types in Winter Park

The View Studio Suites and Event Venue
Front of property

The View Studio Suites and Event Venue

3.5 star property
8.4 out of 10, Very Good, (755)
"Me encanta, opino que deberían de haber más áreas recreativas "
The price is AED 264
AED 298 total
includes taxes & fees
26 Jan - 27 Jan
The View Studio Suites and Event Venue
Lake Buena Vista Resort Village & Spa
Outdoor pool

Lake Buena Vista Resort Village & Spa

4.0 star property
8.4 out of 10, Very Good, (8292)
"Rooms were very clean from the kitchen to the bedrooms. "
Lake Buena Vista Resort Village & Spa
Florida Hotel & Conference Center in the Florida Mall
Exterior

Florida Hotel & Conference Center in the Florida Mall

3.5 star property
9.0 out of 10, Wonderful, (1706)
"The hotel is connected to the Florida mall, a great place to shop and eat. close to other attractions."
The price is AED 693
AED 875 total
includes taxes & fees
25 Jan - 26 Jan
Florida Hotel & Conference Center in the Florida Mall
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.

Frequently asked questions

How much do cottages in Winter Park cost?
Prices for cottages in Winter Park range between AED 219 and AED 477 per night. No matter your budget, you’re sure to find an ideal place to immerse yourself in nature. 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 great cottages in Winter Park, so get set for a memorable stay close to nature. If you have a fixed budget, choose how much you’d like to spend and your preferred property star rating. Or, make your way to the filters to search for cottages with a pool or a hot tub. We’ll help you find the perfect pad whatever your style of travel or plans.
How can I find cheap cottages in Winter Park?
With Expedia’s user-friendly filter tool, sourcing cheap cottages in Winter Park couldn’t be simpler. To view accommodations that’ll make your wallet happy, narrow your search results by star rating, budget and amenities.