The best rentals from the top sites, all in one place

We believe finding a vacation rental in Winter Park should be easy and not take hours of searching and scrolling. We’ve designed VacationRenter from the ground up to help travelers find the perfect rental faster and easier.

Where to stay in Winter Park

Vacation rentals in Winter Park

There are 191 vacation rentals near Winter Park for all manner or mood of travel, availability of time off, and size of budget. So, if you are hoping for an affordable Winter Park vacation, you can find 10% rentals under $41/night. Or if you are willing to splurge on a luxury vacation in Winter Park, there are 19 between $234 and $839/night. Whether you are sleeping by yourself or with a significant other, or are travelling with a group of 21 there are short term home and apartment rentals in Winter Park to fit your Florida vacation needs. The most popular types of short-term rental homes in Winter Park are houses, private rooms and apartments. Winter Park has been a frequently searched travel destination this year and continues to grow in popularity. VacationRenter offers a wide selection of vacation rental availability from leading travel sites like VRBO (Vacation Rentals By Owner), Homeaway,, and many more. Search your travel dates to find available Winter Park vacation homes for your trip.

Home-types in Winter Park

Winter Park has a variety of property types for you to consider when booking a trip. Here are the most popular property types in Winter Park:
- Beach191 vacation rentals
- House106 vacation rentals
- Private Room45 vacation rentals
- Condo35 vacation rentals
- Apartment35 vacation rentals

Points of interests in Winter Park

Winter Park has several popular points of interest for you to check out when visiting the area. Here are the most popular points of interest in Winter Park:
- Winter Park History Museum: 50 vacation rentals
- Community Playground: 48 vacation rentals
- Central Park: 43 vacation rentals
- Downtown Winter Park: 15 vacation rentals
- Kraft Azalea Garden: 14 vacation rentals
- Scenic Boat Tour: 12 vacation rentals