2,756 Winter Park Holiday Rentals

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Compare Winter Park holiday rentals from 12 rental sites including HomeAway, Booking.com, PerfectPlaces and more, from $25 a night.

Information about Winter Park

Vacation Rentals in Winter Park

Looking for a vacation rental in Winter Park? Tripping.com has 2756 rental homes available in Winter Park. Potential renters will find 57 studios, 964 1-bedroom, 828 2-bedroom and 907 rentals with 3 or more bedrooms from $25 a night. Many of these properties are instantly bookable.

The average price of a nightly rental in Winter Park is $282 while the average price of a weekly rental is $1541. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Winter Park home is $7061.

Wondering if you can bring your favorite dog or cat with you? We have 192 pet friendly vacation rentals available for you. In addition to accommodating pets, Winter Park rentals offer a variety of amenities. In particular, 2226 rentals have internet and wifi, 1982 have TV and/or cable and 898 have a pool or hot tub.

Search properties from 12 rental sites in Winter Park where the top providers in that area are HomeAway, Booking.com, and PerfectPlaces. There are 1603 HomeAway rentals, 416 Booking.com short term rentals and 406 PerfectPlaces vacation rentals.