Winter Park, a suburban city in central Florida, was founded as a resort community over 100 years ago. Development began around 1880 with construction of the South Florida Railroad track. Winter Park has long been a destination for celebrities and prominent political figures, including Frank Sinatra, Ray Charles, and Nancy and Ronald Reagan. Its warm climate allows for year-round festivals, such as the annual Bach festival and the Sidewalk Art Festival. Travelers will find shopping, museums, and parks to enjoy in the City of Culture and Heritage!
Winter Park features many museums and art galleries. The most famous of these is perhaps the Charles Hosmer Morse Museum of American Art, which is home to the world’s largest collection of Tiffany glass. Check out the Albin Polasek Museum and Sculpture Gardens for an affordable tour of the artist’s house, property, and work. Its proximity to Lake Osceola allow visitors to spend a pleasant afternoon viewing art and relaxing by the water.
Perched next to scenic Lake Osceola, Winter Park has several opportunities for water recreation. Take a scenic boat tour of the lake, or try renting a paddleboard for a more adventurous way to explore the waterscape! Enjoy views of Cyprus trees and stately lakeside homes from your vantage point on the water.
Visit Park Avenue, a charming street near downtown Winter Park, for clothing boutiques, bistros, and bookstores. Its old buildings and low-hanging Cyprus trees are reminiscent of Disneyland’s New Orleans Square. Featuring over 140 shops, Park Avenue is certain to have something for every traveler. It is also known as a dog-friendly area!
Merely 15 minutes away, Orlando is a dynamic city most notably containing many theme parks. Epcot, Universal Studios, and Sea World are all within the city limits, making Orlando a family-friendly destination. If you’re looking to escape the crowds, take a stroll through the Harry P. Leu Gardens, a 50-acre sanctuary in the midst of a bustling city. There are also numerous highly-rated spas.
Daytona Beach, known for the Daytona 500 NASCAR race, is an hour’s drive from Winter Park. Visit the Daytona International Speedway for races and tours—fanatics can even drive around the track at the Richard Petty Driving Experience! Other attractions include the Boardwalk and pier, the Ponce de Leon Inlet Lighthouse and Museum, and the beach itself.
Out-of-state visitors may be inclined to take the 4-hour drive to Everglades National Park at the southern tip of Florida. This 1.5-million-acre sanctuary is home to turtles, alligators, and many types of birds. There is hiking for all levels, bird watching, and water recreation here.
A quick search on Tripping.com yields nearly 1,000 results for vacation rentals near Winter Park. Many homes retain the area’s Spanish-style charm with porches to enjoy the year-round warm weather. Search for a lakeside property to enjoy Winter Park’s abundant opportunities for water recreation.
Out of town visitors can choose between Orlando International Airport and Orlando Sanford International Airport to bring them to Winter Park. Winter Park can also be accessed by car via Interstate 4 from the north and the south.
Looking for the perfect vacation rental for your Winter Park getaway? Tripping.com’s got you covered. Whether you’re seeking a vacation home, cabin rental or cottage, Winter Park offers 151 affordable vacation home rentals to choose from, with far more amenities, space and comforts than the average hotel room. Select from 131 properties with high-speed WiFi Internet, 54 full with jacuzzi and pool, and homes complete with outdoor patio, great for entertaining with guests. Whatever your needs, find the perfect home rental that best matches your accommodation style and budget.For travelers planning for an extended stay, long-term lodging and corporate rentals only cost an average of $25 a month. Save hundreds with affordable vacation rentals on Tripping.com and, in many cases, book directly online so you’re all set to go. Winter Park has 151 gorgeous homes with 35 pet-friendly rentals to choose from, perfect for your dog or cat. Check out our vacation rental listings now to get the latest deals, and book the right vacation home rental for you and the whole family. Feel at home wherever you are and experience an unforgettable vacation with Tripping.com.
Search properties from 8 vacation rental sites in Winter Park where the top providers in that area are HomeAway, TripAdvisor, and Expedia. There are 84 HomeAway rentals, 31 TripAdvisor short term rentals and 12 Expedia vacation rentals.