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.
Find the best Winter Park vacation rentals with Tripping.com. Choose from 89 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $40 a night to $571 a night.
Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? of homes in Winter Park offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the rentals with pool or jacuzzi, or relax with the family in one of the homes with cable TV.
For all those dog lovers and cat lovers, Winter Park offers pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.Search properties from 7 rental sites in Winter Park where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 49 HomeAway rentals, 26 TripAdvisor short term rentals and 7 Booking.com vacation rentals.