Winter Park, FL, USA

Winter Park, FL, USA

We found 417 vacation rentals — enter your dates for availability


Find the best place to stay — Winter Park

Where to stay around Winter Park?

Our 2018 property listings offer a large selection of 417 vacation rentals near Winter Park. From 148 houses to 108 condos, 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.

What are the popular points of interest near where I can stay when traveling to Winter Park?

HomeAway offers a large selection of vacation rentals near lovely places in Winter Park. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Rollins College: 3,368 vacation rentals
  • Winter Park Village: 2,777 vacation rentals
  • Florida Hospital Orlando: 5,529 vacation rentals
  • Casa Feliz Historic Home Museum: 2,504 vacation rentals
  • Winter Park Country Club: 2,483 vacation rentals

But there are many other points of interest around Winter Park listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent houses in Winter Park?

Yes, of course. HomeAway has 148 houses in Winter Park. Our other popular types of vacation rentals in Winter Park include:

  • Condos: 108 rentals available
  • Apartments: 50 rentals available
  • Villas: 34 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including townhomes and more.

Can I rent golf rentals in Winter Park?

Absolutely, HomeAway has 126 golf rentals in Winter Park. You have also many other possibilities in Winter Park area, including:

  • Downtown rentals: 65 rentals
  • Lake rentals: 45 rentals
  • Waterfront rentals: 36 rentals

Please use our search bar to access the selection of vacation rentals.

Can I find a vacation rental with pool in Winter Park?

Yes, you can select your preferred vacation rental with pool among our 251 vacation rentals with pool available in Winter Park. Please use our search bar to access the selection of vacation rentals available.

    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.