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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Cottages in Winter Park

Orlando Lakefront Tiny House Community
The Club House | 2 bedrooms, individually decorated, individually furnished

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (323)
"We enjoyed our stay, I loved the the view of the lake from the main bedroom ,it’s a beautiful and relaxing place."
The price is AED 268
AED 570 total
includes taxes & fees
20 Jul - 21 Jul
Orlando Lakefront Tiny House Community
Tiny Hidden Cottage
Interior

Tiny Hidden Cottage

9.2 out of 10, Wonderful, (47)
"Host provided eggs from chickens that roost on the property - nice extra!"
The price is AED 290
AED 563 total
includes taxes & fees
19 Jul - 20 Jul
Tiny Hidden Cottage
Charming 2-bedroom Country Cottage in Kissimmee with private parking
Fridge, microwave, oven, stovetop

Charming 2-bedroom Country Cottage in Kissimmee with private parking

10.0 out of 10, Exceptional, (2)
"The house was exactly as shown. It was very clean and really nice. Great space for parking my large trailer. The neighborhood was nice and very quiet. We would definitely stay again."
The price is AED 422
AED 553 total
includes taxes & fees
28 Jul - 29 Jul
Charming 2-bedroom Country Cottage in Kissimmee with private parking
Florida Guest House with Private pool & WiFi
Outdoor pool

Florida Guest House with Private pool & WiFi

9.8 out of 10, Exceptional, (38)
"Wonderful stay. This is my second time here and love the accommodations and location. Very quiet. "
The price is AED 374
AED 905 total
includes taxes & fees
26 Jul - 27 Jul
Florida Guest House with Private pool & WiFi
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
Private Patio: College Park Cottage in Orlando!
Outdoor dining

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!
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
2 bedrooms, in-room safe, desk, iron/ironing board

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

10.0 out of 10, Exceptional, (24)
"Easy and convenient in a nice place "
The price is AED 641
AED 1,274 total
includes taxes & fees
28 Jul - 29 Jul
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
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)
"This property was excellent and lived up to the expectations in the post! So close to the parks, we came back everyday to cool down by the pool and recharge our batteries."
Modern Townhome W/private Pool & Free Water Park!
The Pink Door Cottage-Historic Sanford
Outdoor dining

The Pink Door Cottage-Historic Sanford

9.8 out of 10, Exceptional, (17)
"Fully equipped with everything one could need whilst staying here."
The Pink Door Cottage-Historic Sanford
16 Mi to Disney: Cottage w/ Deck in Winter Garden
Fridge, microwave, stovetop, dishwasher

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

10.0 out of 10, Exceptional, (12)
"This place was amazing! The location is perfect and the house is sooo cute! Would stay again for sure!!"
16 Mi to Disney: Cottage w/ Deck in Winter Garden
Deltona Lake House, Day Trip to Disney & Universal
House (2 Bedrooms) | Interior

Deltona Lake House, Day Trip to Disney & Universal

3.0 star property
10.0 out of 10, Exceptional, (3)
"This house was perfect! Very spacious, clean, and felt like a very safe neighborhood for a few women traveling. The ONLY improvements I would suggest would be having more towels, and extra blankets available for guests. And I would replace the pull out couch mattress as it was very uncomfortable. Still a 10/10 overall!"
Deltona Lake House, Day Trip to Disney & Universal
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
Orlando Home w/ Private Pool: 10 Mi to UCF Campus!
Paper towels

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

3.0 star property
Orlando Home w/ Private Pool: 10 Mi to UCF Campus!
Luxurious Home W/private Pool, Near Disney!
Outdoor 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!
Comfortable 4BR Getaway: Wifi & Parking Included
House (4 Bedrooms) | Floor plan

Comfortable 4BR Getaway: Wifi & Parking Included

3.0 star property
Comfortable 4BR Getaway: Wifi & Parking Included
Orlando Golden Girls Retreat: Prime Location!
House (1 Bedroom) | Interior

Orlando Golden Girls Retreat: Prime Location!

3.0 star property
Orlando Golden Girls Retreat: Prime Location!
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 264
AED 685 total
includes taxes & fees
20 Jul - 21 Jul
Downtown Cottage
Chic Orlando Family Getaway w/ Fenced Yard!
House (4 Bedrooms) | Front of property

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!
14 Mi to Universal Studios: Central Orlando Home
Interior

14 Mi to Universal Studios: Central Orlando Home

3.0 star property
14 Mi to Universal Studios: Central Orlando Home
Cozy Tiny Home Near Disney World & Orlando Parks!
Fridge, microwave, oven, stovetop

Cozy Tiny Home Near Disney World & Orlando Parks!

8.2 out of 10, Very Good, (10)
"My husband and I stayed at this property while going to disney. Perfect size for us! Great property "
Cozy Tiny Home Near Disney World & Orlando Parks!
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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Frequently asked questions

How much do cottages in Winter Park cost?
Cottages in Winter Park range between AED 264 and AED 641 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.