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Check prices for these dates

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Aug 29 - Aug 31
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Sep 5 - Sep 7
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Sep 19 - Sep 21
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Oct 17 - Oct 19

Browse Select Winter Park Cottages

Orlando Lakefront Tiny House Community
The Sunshine Lake Shake

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (328)
"We enjoyed our stay."
The price is CA $106
CA $220 total
includes taxes & fees
Aug 25 - Aug 26
Orlando Lakefront Tiny House Community
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 CA $62
CA $215 total
includes taxes & fees
Aug 21 - Aug 22
Downtown Cottage
Tiny Hidden Cottage
Interior

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (49)
"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 CA $98
CA $199 total
includes taxes & fees
Aug 21 - Aug 22
Tiny Hidden Cottage
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 $138
CA $185 total
includes taxes & fees
Aug 27 - Aug 28
Charming 2-bedroom Country Cottage in Kissimmee with private parking
The Sanford Foodie Guest House
1 bedroom, desk, WiFi, bed sheets

The Sanford Foodie Guest House

8.6 out of 10, Excellent, (12)
"Cozy little place to stay"
The price is CA $69
CA $350 total
includes taxes & fees
Sep 1 - Sep 2
The Sanford Foodie Guest House
Incredible Private Lakefront Cottage Retreat
Exterior

Incredible Private Lakefront Cottage Retreat

10.0 out of 10, Exceptional, (27)
"One of our best stays. "
The price is CA $137
CA $408 total
includes taxes & fees
Aug 21 - Aug 22
Incredible Private Lakefront Cottage Retreat
Weekday Special Orlando Cozy Cottage with queen bed & nearby pickleball courts
Property grounds

Weekday Special Orlando Cozy Cottage with queen bed & nearby pickleball courts

10.0 out of 10, Exceptional, (15)
"Great place, will stay again"
The price is CA $145
CA $342 total
includes taxes & fees
Sep 18 - Sep 19
Weekday Special Orlando Cozy Cottage with queen bed & nearby pickleball courts
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
Property grounds

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 "
The price is CA $189
CA $445 total
includes taxes & fees
Sep 16 - Sep 17
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
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 CA $247
CA $489 total
includes taxes & fees
Sep 1 - Sep 2
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 International Airport

Hyatt Regency Orlando International Airport

10/10 Excellent
"Easy"
Edmond 1-night trip
Posted 11 hours ago
Hyatt Regency Orlando International Airport