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7 Saf. - 9 Saf.

In two weeks

14 Saf. - 16 Saf.

In one month

28 Saf. - 2 Rab. I

In two months

28 Rab. I - 30 Rab. I

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

"The views are absolutely incredible. Every time I go to Orlando, I stay here"

SAR 578 total

includes taxes & fees

23 Feb - 24 Feb

"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!"

SAR 1,634 total

includes taxes & fees

3 Feb - 4 Feb

"Cute tiny house. Very clean. Private. I was not happy with the AC window unit in the bedroom as it woke me up whenever it turned on. There is a chicken coop next to it with a rooster that greeted me in the morning. But I love backyard chickens so that was ok. Would be nice to provide ice for drinks and cream for coffee. Thanks. "

SAR 588 total

includes taxes & fees

13 Feb - 14 Feb

"Great spot if you are visiting the area. The host was nice and helpful!"

SAR 827 total

includes taxes & fees

3 Feb - 4 Feb

"Very much enjoyed our stay. Weather didn’t allow pool use; but I’m sure it would have been great."

SAR 1,025 total

includes taxes & fees

3 Mar - 4 Mar

"Perfect location house was just what is described "

"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!"

SAR 817 total

includes taxes & fees

10 Feb - 11 Feb

Winter Garden Vacation Rental | 3BR | 2BA | 1,200 Sq Ft | 3 Steps to Enter

"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...

"Suite was super comfy and attention to detail in furnishings was great"

"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. "

"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 . "

"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. "

"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"

"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...

"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."

"It was a nice place ."

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Other property types in Winter Park

"Large rooms"

SAR 342 total

includes taxes & fees

3 Feb - 4 Feb

"Great property to stay at and fantastic staff!! "

"Hooked onto a very good shopping mall. Plenty of "eats" everywhere. Maybe the only negative is extra fees."

SAR 936 total

includes taxes & fees

3 Feb - 4 Feb

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Frequently asked questions

How much do cottages in Winter Park cost?

Prices for cottages in Winter Park range between and 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?

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Search Cottages in Winter Park

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Check prices for these dates

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

Orlando Lakefront Tiny House Community

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

Tiny Hidden Cottage

The Sanford Foodie Guest House

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

Stunning Lakeview Townhome w/ Private Pool!

Downtown Cottage

Dtwn Winter Garden Home: 12 Mi to Disney!

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

The Pink Door Cottage-Historic Sanford

5003 Windermere Avenue

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

Screened Lanai + Fenced Yard: Luxe Orlando Home

THE HIDEAWAY AT COLLEGE PARK

Caribbean Dreamin

Lake-view Home w/ Game Room in Orlando!

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

Luxurious Home W/private Pool, Near Disney!

Beautiful, Modern Home W/private Pool! Near WDW

Close to Attraction: Home in Orlando

Other property types in Winter Park

The View Studio Suites and Event Venue

Lake Buena Vista Resort Village & Spa

Florida Hotel & Conference Center in the Florida Mall

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