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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
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Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Winter Park Cottages

Orlando Lakefront Tiny House Community
Relax in a serene outdoor space with a deck overlooking a tranquil body of water, surrounded by lush greenery.

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (327)
"We enjoyed our stay."
The price is CA $89
CA $201 total
includes taxes & fees
Sep 8 - Sep 9
Orlando Lakefront Tiny House Community
Tiny Hidden Cottage
Enjoy a meal with a view from this kitchen, featuring a large window and a potted plant.

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (48)
"Host provided eggs from chickens that roost on the property - nice extra!"
The price is CA $98
CA $198 total
includes taxes & fees
Aug 10 - Aug 11
Tiny Hidden Cottage
5003 Windermere Avenue
Relax by the pool with a meal at this outdoor dining area, featuring a table and chairs under a pendant light.

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
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
Stroll through a serene garden with lush greenery, neatly trimmed hedges, and a variety of flowering plants.

Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,

8.4 out of 10, Very good, (15)
"This was a cute place in a nice neighborhood "
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
Private Patio: College Park Cottage in Orlando!
Welcome to a serene single-story home surrounded by a lush lawn and a majestic tree.

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!
Residents can enjoy a central swimming pool complex surrounded by well-maintained lawns and pathways.

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!
Dtwn Winter Garden Home: 12 Mi to Disney!
Cozy home with a covered porch and a beautiful tree-lined yard.

Dtwn Winter Garden Home: 12 Mi to Disney!

10.0 out of 10, Exceptional, (13)
"We had a wonderful stay in Analia’s home. It was a perfect location and 4 adults were quit comfortable for two weeks. "
Dtwn Winter Garden Home: 12 Mi to Disney!
The Pink Door Cottage-Historic Sanford
Relax in this charming gazebo with a dining table and comfortable seating.

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
Labor Day Getaway!! Guest House with Private pool & WiFi
Welcome to a charming single-story home with a red door, surrounded by lush greenery and a wooden fence.

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
Lovely Spacious Guesthouse in Mills 50 District, Orlando
Enter a cozy retreat with a warm and inviting atmosphere, featuring a glass door, wooden fence, and string lights.

Lovely Spacious Guesthouse in Mills 50 District, Orlando

10.0 out of 10, Exceptional, (1)
"Loved this space, by great locations. Can’t wait to visit again."
Lovely Spacious Guesthouse in Mills 50 District, Orlando
16 Mi to Disney: Cottage w/ Deck in Winter Garden
Two-bedroom house with a front porch and yard, perfect for a family getaway.

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
~ 12 Mi to Disney: Downtown Winter Garden Cottage!
Escape to a peaceful retreat with a charming single-story house featuring a quaint porch and a welcoming front yard with a small garden.

~ 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!
Deltona Lake House, Day Trip to Disney & Universal
House (2 Bedrooms) | Front of property

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!
Stroll up the pathway to the charming front door, featuring a glass panel, and enter a serene home surrounded by lush trees and a beautifully manicured lawn.

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!
Residents enjoy a central pool complex with water features and a basketball court, surrounded by green spaces and clear pathways.

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!
Charming 2-bedroom Country Cottage in Kissimmee with private parking
Exterior

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 CA $144
CA $191 total
includes taxes & fees
Aug 18 - Aug 19
Charming 2-bedroom Country Cottage in Kissimmee with private parking
Comfortable 4BR Getaway: Wifi & Parking Included
Stunning home with a beautifully manicured lawn and a charming front porch.

Comfortable 4BR Getaway: Wifi & Parking Included

3.0 star property
Comfortable 4BR Getaway: Wifi & Parking Included
Downtown Cottage
Two single beds with matching headboards and footboards, a ceiling fan, and a large window with vertical blinds.

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 CA $80
CA $234 total
includes taxes & fees
Aug 10 - Aug 11
Downtown Cottage
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Traditional home with a gabled roof and front porch, surrounded by lush gardens.

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 CA $247
CA $486 total
includes taxes & fees
Aug 11 - Aug 12
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
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

Hyatt Regency Orlando

Hyatt Regency Orlando

10/10 Excellent
"We loved every moment of it "
Emil 3-night trip
Posted 8 hours ago
Hyatt Regency Orlando