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Price $10 - $1000+

1,390 Winter Park Holiday Rentals, Houses & Apartments

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews. Compare Winter Park holiday rentals from 14 rental sites including TripAdvisor, Booking.com, HomeAway, and more, ranging from $30 to $1050 a night. 
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    Information about Winter Park

    About Winter Park

    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!

    Things to do in Winter Park

    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!

    Day Trips from Winter Park

    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.

    Accommodation in Winter Park

    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.

    Transportation in Winter Park

    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.

    Vacation Rentals in Winter Park

    Save hundreds with a Tripping.com vacation rental and forget about the expensive hotel room. For the ultimate getaway trip, Winter Park offers 1,390 vacation home rentals for an affordable price to match your budget and accommodation needs. Book one now for an average price of $155 a night, or a long-term rental for an average price of $3562 a month.

    These homes offer a range of amenities, giving you more bang for your buck. For those looking to stay in a corporate rental, 568 of Winter Park’s rentals offer high speed internet so you can easily keep in touch with your company or team. Go for a swim at one of the 267 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 1,108 cozy homes.

    Traveling with pets? Choose from 108 pet-friendly rentals in Winter Park for a quality experience. Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your furry buddy. Book instantly with properties marked “Instabook”, and check out our other listings now to find the perfect vacation home for you.

    Search properties from 14 rental sites in Winter Park where the top providers in that area are TripAdvisor, Booking.com, and HomeAway. There are 541 TripAdvisor rentals, 532 Booking.com short term rentals and 172 HomeAway vacation rentals.