- Rollins College: Rollins College is a private, liberal arts college located in Winter Park. Founded in 1885, it is known for its strong academics and beautiful campus.
- The Charles Hosmer Morse Museum of American Art: The Morse Museum is home to one of the world's most comprehensive collections of works by Louis Comfort Tiffany. It also features a collection of American art from the late 19th and early 20th centuries.
- The Albin Polasek Museum & Sculpture Gardens: The Polasek Museum is dedicated to the work of Albin Polasek, a Croatian-born American sculptor. It features a collection of his sculptures, as well as a beautiful sculpture garden.
- The Central Park: The Central Park is a 121-acre park located in the heart of Winter Park. It features lakes, gardens, walking trails, and playgrounds.
- Park Avenue: Park Avenue is the main street in Winter Park and is lined with shops, restaurants, and galleries. It is a popular spot for locals and tourists to stroll and shop.
- Boat Tours: Winter Park is home to several lakes, and there are several boat tour companies that offer cruises of the lakes. These tours provide a unique perspective of the area.
- Annual Festivals: Winter Park is known for its annual festivals, including the Winter Park Sidewalk Art Festival, the Winter Park Jazz Festival, and the Winter Park Food & Wine Festival.