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 205 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 $35/night. Or if you are willing to splurge on a luxury vacation in Winter Park, there are 21 between $235 and $796/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:
- Beach205 vacation rentals
- House105 vacation rentals
- Private Room46 vacation rentals
- Condo32 vacation rentals
- Apartment32 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:
- Harry P Leu Gardens: 2,103 vacation rentals
- Martin Luther King, Jr. Park: 1,366 vacation rentals
- Community Playground: 1,366 vacation rentals
- Hannibal Square Heritage Center: 1,366 vacation rentals
- Knowles Memorial Chapel: 1,366 vacation rentals
- Winter Park History Museum: 1,366 vacation rentals
- Shady Park: 1,366 vacation rentals
- Howell Branch Preserve Pavilion: 1,366 vacation rentals
- Kraft Azalea Garden: 1,366 vacation rentals