78 Winter Park Holiday Rentals

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Compare Winter Park holiday rentals from 16 rental sites including TripAdvisor, Booking.com, HomeAway and more, ranging from $25 to $2835 a night.

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

Looking for a vacation rental in Winter Park? Tripping.com has 1676 rental homes available in Winter Park. Potential renters will find 2 studios, 754 1-bedroom, 214 2-bedroom and 706 rentals with 3 or more bedrooms ranging from $25 a night to $2835 a night. Many of these properties are instantly bookable.

The average price of a nightly rental in Winter Park is $153 while the average price of a weekly rental is $1310. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Winter Park home is $3788.

Wondering if you can bring your favorite dog or cat with you? We have 144 pet friendly vacation rentals available for you. In addition to accommodating pets, Winter Park rentals offer a variety of amenities. In particular, 729 rentals have internet and wifi, 1244 have TV and/or cable and 449 have a pool or hot tub.

Search properties from 16 rental sites in Winter Park where the top providers in that area are TripAdvisor, Booking.com, and HomeAway. There are 624 TripAdvisor rentals, 547 Booking.com short term rentals and 218 HomeAway vacation rentals.
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