Winter Park, FL, USA

Winter Park, FL, USA

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Where to stay near Winter Park, FL?

Our 2018 property listings offer a large selection of 1,711 vacation rentals near Winter Park. From 778 condos to 300 houses, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Winter Park for a holiday or a weekend are on HomeAway.

Follow in the footsteps of presidents in Winter Park

It might be hard to believe that well-to-do Winter Park hides just north of Orlando's wild rollercoasters and world-famous theme parks, but it does. Winter Park vacation rentals come steeped in southern charm, surrounded by sultry, palm-swaying gardens, willow-peppered parks, wildflower meadows, and other gorgeous tropical green spaces. They offer a gateway to a refined and warm Floridian hotspot, where boating tours and azalea blooms are the name of the game.

Wander between the palm trees and the art galleries

Arty types certainly won't be disappointed by the wealth of galleries and museums that peppers the downtown of Winter Park. Ranging from off-beat jewelry exhibitions to prestigious fine-art collections of American greats, there's all sorts of creative showcases to wonder at. If you'd prefer to stay out in the warm Floridian weather, then you could also consider a boating trip up and down the winding canals that shoot through the resort, or simply search for a Winter Park vacation rental with a sun-splashed veranda overlooking Lake Virginia.

Art, architecture, and American cuisine in Winter Park

Scenic Olde Winter Park is surely the main attraction in this classic resort town in the heart of the Sunshine State. A warren of cobbled lanes and hidden squares that shoulders up against Lake Virginia, it's cut through by babbling canals and comes with hearty American bistros touting stacked burgers and spicy Tex-Mex. Close by, the Charles Hosmer Morse Museum can be seen hiding behind rows of swaying palm trees, hosting the dazzling glass mosaic works and jewelry of Louis Comfort Tiffany. And after that, be sure to hit the award-winning campus grounds of Rollins College – it's considered one of the most beautiful in the whole country.

Enjoy the sultry Florida heat in Winter Park

Winter Park was named because of its popularity with well-to-do American tycoons and VIPs during the colder months, promising warm temperatures and laid-back living on the lakesides between December and March. Not much has changed. Folk still flock here to wander the wildflower meadows and take boating tours when icy weather is buffeting the northern states. This is when you're likely to find the local eateries and country clubs at their most lively and inviting. Other travelers will head in for the Sidewalk Art Festival in March, when you'd do well to look for Winter Park vacation rentals down Park Avenue, between the street entertainers and food stalls.

Winter Park: Peppered by Florida's lakes

Winter Park is encompassed by countless lakes and reservoirs, giving it an enviable location between some of Florida's most beautiful waterways. You can opt to hit the canals and boat through the ponds to explore the rolling flatlands and oak-peppered swamps. Or, you can stay on dry land and adventure all the way to downtown Orlando on bike or foot via the popular Cady Way Trail. To immerse yourself even deeper in the tropical heart of the Sunshine State, there's always the chance to go on safari on Lake Jesup, where you can witness gators and rare wetland birds.