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Private Vacation Homes in Winter Park

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Winter Park Cabin Rentals

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Vacation Condos in Winter Park

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All Vacation Rentals in Winter Park

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Winter Park Vacation Rentals

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.

Save Big on Vacation Rental Packages

The Berkley, Orlando
Bluegreen Vacations Orlando's Sunshine Resort
Luxury 15 Bedroom Suites Home for 30 Guests
Amazing Home With 2 Themed Bedrooms
Spacious Vacation Home With Pool Jacuzzi Near Disney