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Winter Park Vacation Rentals Winter Park is a city in Orange County, Florida, United States. The population was 24,090 at the 2000 census. According to the U.S. Census Bureau's 2006 estimates, the city had a population of 28,083. The city is home to Rollins College, Full Sail Real World Education and the Charles Hosmer Morse Museum of American Art, which houses the largest collection of Tiffany glass on Earth. Winter Park enjoys more parkspace per capita than any other city in Florida. Winter Park was founded as a resort destination by wealthy New England Industrialists before the turn of the 20th century. It is recognized as the first centrally planned community in Florida; its main street includes not only public civic buildings and retail, but also art galleries, a private liberal arts college, museums, a park, a train station, a golf course country club, a historic cemetery, and a beach and boat launch. Winter Park is celebrated for a sense of place and history, uncommon to many parts of Central Florida. Many structures are more than 100 years old. The scenic "olde Winter Park" area is punctuated by small, winding brick streets, and a canopy of old Southern Live Oak and Camphor trees, draped with Spanish Moss. The city draws thousands of visitors to annual festivals including the Bach Festival, the nationally ranked Sidewalk Art Festival, and the Winter Park Concours d'Elegance.
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