Plan for peace of mind

Some properties allow cancellations up to 14 days before arrival. Check the policy before booking.

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Can I find a vacation rental around Winter Park?

Yes, our 2020 property listings offer a large selection of 517 vacation rentals near Winter Park. From 255 Houses to 39 Condos/Apartments, 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 is the best area to stay when traveling to Winter Park?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Winter Park:

  • Summit Estates: 328 vacation rentals
  • Boulder Bay: 682 vacation rentals
  • Fox Farm: 585 vacation rentals
  • Castle Glen Estates: 550 vacation rentals
  • Evergreen Estates: 1,085 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

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:

  • Bear Mountain: 2,269 vacation rentals
  • Boulder Bay Park: 3,011 vacation rentals
  • Lakeview Shopping Center: 2,898 vacation rentals
  • Big Bear Discovery Center: 2,954 vacation rentals
  • North Shore Recreation Area: 2,954 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 255 Houses in Winter Park. Our other popular types of vacation rentals in Winter Park include:

  • Condos/Apartments: 39 rentals available
  • Cabins: 118 rentals available
  • Cottages: 118 rentals available

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

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

Yes, you can select your preferred vacation rental with pool among our 69 vacation rentals with pool available in Winter Park. Please use our search bar to access the selection of vacation rentals available.

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