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Vacation Rentals in Winter Park

See all Vacation Rentals in Winter Park
$100
Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow

Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow

Winter Park, FL
Located in Goldenrod, this historic vacation home is 1.9 mi (3 km) from Full Sail University and within 6 mi (10 km) of Rollins College and Winter Park Village. Albin Polasek Museum and Sculpture Gardens and Kraft Azalea Gardens are also within 6 mi (10 km).
Cute Guest House In Winter Park Minutes From Downtown in Car

Cute Guest House In Winter Park Minutes From Downtown in Car

Winter Park, FL
This apartment features barbecue grills.
Amazing Location- Walk to Everything

Amazing Location- Walk to Everything

Winter Park, FL
This condo features a water park, a garden, and barbecue grills.
$304
Lounge on Blue Velvet Couches at a Charming Hideaway

Lounge on Blue Velvet Couches at a Charming Hideaway

Winter Park, FL
Situated in Winter Park, this vacation home is within 1 mi (2 km) of Casa Feliz Historic Home Museum and Winter Park Village. Orlando Science Center and Rollins College are also within 3 mi (5 km). Winter Park Station is 21 minutes by foot.
Mid Century Luxury, 1 Block From Park Ave

Mid Century Luxury, 1 Block From Park Ave

Winter Park, FL
This apartment features a water park and a garden.
Just Like Home... With A Pool!

Just Like Home... With A Pool!

Winter Park, FL
This family-friendly Winter Park vacation home is within 3 mi (5 km) of Red Bug Lake Park and Full Sail University. Kraft Azalea Gardens and Rollins College are also within 6 mi (10 km).
Family Home With Flexible Schedule

Family Home With Flexible Schedule

Winter Park, FL
A spa tub is featured at this vacation home, along with a garden and barbecue grills.
Cute Bungalow Minutes Walk From Park Avenue

Cute Bungalow Minutes Walk From Park Avenue

Winter Park, FL
Situated in Winter Park, this vacation home is within 1 mi (2 km) of Morse Museum of American Art and Rollins College. Orlando Science Center and Winter Park Village are also within 3 mi (5 km). Winter Park Station is 10 minutes by foot.
Mid Century Luxury, 1 Block From Park Ave

Mid Century Luxury, 1 Block From Park Ave

Winter Park, FL
Located in the heart of Winter Park, this historic apartment building is within a 15-minute walk of Morse Museum of American Art and Rollins College. Orlando Science Center and Winter Park Village are also within 3 mi (5 km). Winter Park Station is 8 minutes by foot.
Comfy Home in Winter Park, can Accommodate up 6 Guests!

Comfy Home in Winter Park, can Accommodate up 6 Guests!

Winter Park, FL
This vacation home includes a garden and barbecue grills.
Casa Aloma

Casa Aloma

Winter Park, FL
A garden is available at this vacation home.
Casa Justine

Casa Justine

Winter Park, FL
A spa tub is featured at this vacation home, along with a garden.
Lounge on Blue Velvet Couches at a Charming Hideaway

Lounge on Blue Velvet Couches at a Charming Hideaway

Winter Park, FL
Situated in Winter Park, this vacation home is within 1 mi (2 km) of Casa Feliz Historic Home Museum and Winter Park Village. Orlando Science Center and Rollins College are also within 3 mi (5 km). Winter Park Station is 21 minutes by foot.
Winter Park charm. Close to Park Ave

Winter Park charm. Close to Park Ave

Winter Park, FL
Situated in Winter Park, this vacation home is within 1 mi (2 km) of Enzian Theater and Winter Park Village. Orlando Science Center and Rollins College are also within 3 mi (5 km). Winter Park Station is 25 minutes by foot.
Casa Winter Park

Casa Winter Park

Winter Park, FL
A garden is available at this vacation home.
Map

The next time you’re looking to get away from it all, head to Winter Park in central Florida. You’ll feel less like a tourist visiting for the first time and more like a local taking a casual stroll when you reserve one of many luxurious Winter Park vacation rentals. Stay within walking distance of the city’s 11-acre Central Park, or use your private accommodation as a resting place between trips to nearby Walt Disney World® and Universal Orlando.

The Local Life

Home to a charming downtown district with brick-lined streets, Winter Park is the perfect vacation destination for those who want to slow down and enjoy life for a while. Instead of driving all over town, stay in the heart of all the action by booking a convenient apartment rental in the center of the city. Once in your chosen accommodation, you can wake up at your leisure and wander into an inviting café for a light breakfast of croissants and cappuccinos. Snap a few photos of the stunning oak trees around the city, and take in the massive amount of vegetation inside the city’s Mead Botanical Garden. After exploring the Charles Hosmer Morse Museum of American Art, retreat to your quiet accommodation for an evening of sipping local wine on your personal patio.

For travelers looking to perfect their swing on the green during their trip to Florida, there’s no better place to stay than Extended Stay America, as its location is close to several golf courses. Traveling with the family in tow? Stay at the DoubleTree by Hilton Orlando Airport and enjoy the area’s many theme parks and attractions while staying reasonably close to Orlando International Airport. Travelocity offers accommodations throughout Florida—including Winter Park and Orlando—that will open up a world of possibility for your travels. Peruse the array of options we have available today, and start planning your picture-perfect trip to Winter Park.


*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.