Find Vacation Rentals in Winter Park, Orange County

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Winter Park
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House Winter Park
e.g. 5/13 - 5/20 (Sat - Sat)
$147 per night
House ∙ 6 guests ∙ 3 bedrooms
4.7
"Outstanding" (76 ratings)
Winter Park, Orange County, Florida, United States
Free cancellation
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Vrbo
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House Winter Park
e.g. 4/1 - 4/8 (Sat - Sat)
$352 per night
House ∙ 6 guests ∙ 3 bedrooms
4.8
"Excellent" (173 ratings)
Winter Park, Orange County, Florida, United States
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Vrbo
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House Winter Park
e.g. 6/3 - 6/10 (Sat - Sat)
$373 per night
House ∙ 8 guests ∙ 4 bedrooms
4.9
"Excellent" (49 ratings)
Winter Park, Orange County, Florida, United States
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Vrbo
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Cottage Winter Park
e.g. 8/27 - 9/3 (Sat - Sat)
$246 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (15 ratings)
Winter Park, Orange County, Florida, United States
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Vrbo
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House Winter Park
e.g. 9/17 - 9/24 (Sat - Sat)
$150 per night
House ∙ 3 guests ∙ 1 bedroom
5.0
"Excellent" (3 ratings)
Winter Park, Orange County, Florida, United States
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Vrbo
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Apartment Winter Park
e.g. 1/28 - 2/4 (Sat - Sat)
$200 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
Free cancellation
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Vrbo
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Condo Winter Park
e.g. 10/15 - 10/22 (Sat - Sat)
$357 per night
Condo ∙ 5 guests ∙ 2 bedrooms
5.0
"Excellent" (19 ratings)
Winter Park, Orange County, Florida, United States
Free cancellation
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Vrbo
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House Winter Park
e.g. 9/17 - 9/24 (Sat - Sat)
-24%
$150
$114 per night
House ∙ 10 guests ∙ 4 bedrooms
4.5
"Outstanding" (6 ratings)
Winter Park, Orange County, Florida, United States
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Vrbo
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Condo Winter Park
e.g. 8/27 - 9/3 (Sat - Sat)
$125 per night
Condo ∙ 4 guests ∙ 1 bedroom
Winter Park, Orange County, Florida, United States
Free cancellation
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Vrbo
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Vacation rentals and apartments with air conditioning

House Aircondition Winter Park
e.g. 4/15 - 4/22 (Sat - Sat)
-26%
$150
$112 per night
House ∙ 6 guests ∙ 3 bedrooms
4.9
"Excellent" (21 ratings)
Winter Park, Orange County, Florida, United States
Free cancellation
Aircondition
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Vrbo
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House Aircondition Winter Park
e.g. 12/9 - 12/16 (Fri - Fri)
-57%
$311
$134 per night
House ∙ 8 guests ∙ 3 bedrooms
4.9
"Excellent" (61 ratings)
Winter Park, Orange County, Florida, United States
Free cancellation
Aircondition
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Vrbo
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House Aircondition Winter Park
e.g. 5/20 - 5/27 (Sat - Sat)
$76 per night
House ∙ 4 guests ∙ 1 bedroom
4.8
"Excellent" (20 ratings)
Winter Park, Orange County, Florida, United States
Free cancellation
Aircondition
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Vrbo
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Vacation rentals with Wi-Fi

House Internet Winter Park
e.g. 12/3 - 12/10 (Sat - Sat)
$160 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
"Excellent" (90 ratings)
Winter Park, Orange County, Florida, United States
Free cancellation
Internet
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Vrbo
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House Internet Winter Park
e.g. 2/4 - 2/11 (Sat - Sat)
$142 per night
House ∙ 12 guests ∙ 3 bedrooms
4.0
"Very good" (8 ratings)
Winter Park, Orange County, Florida, United States
Free cancellation
Internet
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Vrbo
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House Internet Winter Park
e.g. 1/28 - 2/4 (Sat - Sat)
-61%
$425
$167 per night
House ∙ 15 guests ∙ 6 bedrooms
4.6
"Outstanding" (138 ratings)
Winter Park, Orange County, Florida, United States
Free cancellation
Internet
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Vrbo
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Vacation homes and cottages with a garden

House Yard Winter Park
e.g. 6/10 - 6/17 (Sat - Sat)
$373 per night
House ∙ 8 guests ∙ 5 bedrooms
4.9
"Excellent" (93 ratings)
Winter Park, Orange County, Florida, United States
Yard
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Vrbo
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House Yard Winter Park
e.g. 6/3 - 6/10 (Sat - Sat)
$153 per night
House ∙ 5 guests ∙ 3 bedrooms
4.7
"Outstanding" (37 ratings)
Winter Park, Orange County, Florida, United States
Free cancellation
Yard
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Vrbo
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House Yard Winter Park
e.g. 8/8 - 8/15 (Mon - Mon)
-21%
$194
$153 per night
House ∙ 9 guests ∙ 4 bedrooms
4.4
"Very good" (43 ratings)
Winter Park, Orange County, Florida, United States
Yard
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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 $76 per night.

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

You can find and compare 167 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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