Find Vacation Rentals in Winter Park, Orange County

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Winter Park
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Winter Park
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Popular Winter Park Vacation Rentals

Find the perfect Winter Park vacation rental

House Winter Park
from $151 per night
House ∙ 8 guests ∙ 4 bedrooms
Winter Park, Orange County, Florida, United States
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Vrbo
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House Winter Park
from $108 per night
House ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding (51 ratings)
Winter Park, Orange County, Florida, United States
Details
Vrbo
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Details
House Winter Park
from $106 per night
House ∙ 6 guests ∙ 2 bedrooms
4.8
Outstanding (8 ratings)
Winter Park, Orange County, Florida, United States
Details
Vrbo
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Details
House Winter Park
from $169 per night
House ∙ 9 guests ∙ 3 bedrooms
5.0
Outstanding (2 ratings)
Winter Park, Orange County, Florida, United States
Details
Vrbo
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Details
House Winter Park
from $268 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (4 ratings)
Winter Park, Orange County, Florida, United States
Details
Vrbo
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Details
House Winter Park
from $112 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (2 ratings)
Winter Park, Orange County, Florida, United States
Details
Vrbo
Details
Details
Cottage Winter Park
from $186 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (59 ratings)
Winter Park, Orange County, Florida, United States
Details
Vrbo
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Details
House Winter Park
from $207 per night
House ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding (30 ratings)
Winter Park, Orange County, Florida, United States
Details
Vrbo
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Details
House Winter Park
from $259 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (4 ratings)
Winter Park, Orange County, Florida, United States
Details
Vrbo
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Details
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Vacation rentals with Wi-Fi

House  Winter Park
from $89 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (2 ratings)
Winter Park, Orange County, Florida, United States
Internet
Details
HomeToGo
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Details
House  Winter Park
from $230 per night
House ∙ 8 guests ∙ 4 bedrooms
4.0
Very good (1 rating)
Winter Park, Orange County, Florida, United States
Internet
Details
Vrbo
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Details
Apartment  Winter Park
from $128 per night
Apartment ∙ 6 guests ∙ 1 bedroom
5.0
Outstanding
Winter Park, Orange County, Florida, United States
Internet
Details
Vacasa
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Vacation rentals and apartments with air conditioning

Apartment  Winter Park
from $179 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (103 ratings)
Winter Park, Orange County, Florida, United States
Air conditioning
Details
Vrbo
Details
Details
House  Winter Park
from $176 per night
House ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding (36 ratings)
Winter Park, Orange County, Florida, United States
Air conditioning
Details
Vrbo
Details
Details
House  Winter Park
from $323 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding (117 ratings)
Winter Park, Orange County, Florida, United States
Air conditioning
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Vrbo
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Details
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Apartments and vacation rentals with a kitchen

House  Winter Park
from $361 per night
House ∙ 8 guests ∙ 4 bedrooms
4.9
Outstanding (133 ratings)
Winter Park, Orange County, Florida, United States
Kitchen
Details
Vrbo
Details
Details
House  Winter Park
from $406 per night
House ∙ 10 guests ∙ 4 bedrooms
Winter Park, Orange County, Florida, United States
Kitchen
Details
Vrbo
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Details
Apartment  Winter Park
from $170 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding (35 ratings)
Winter Park, Orange County, Florida, United States
Kitchen
Details
Vrbo
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Details
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Frequently Asked Questions

What is the average price per night for accommodation in Winter Park?

In Winter Park, vacation rentals start at $92 per night.

Are there any vacation rentals available to book in Winter Park?

You can find and compare 173 offers in Winter Park and book an ideal place for your next getaway.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Winter Park Information

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.

Popular Day Trips Near Winter Park

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