1,973 Winter Park Vacation Rentals & Short Term Rentals

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Compare Winter Park vacation rentals from 12 rental sites including HomeAway, Booking.com, TripAdvisor and more, ranging from $25 to $1975 a night.

Information about Winter Park

Vacation Rentals in Winter Park

Find the best Winter Park vacation rentals with Tripping.com. Choose from 1977 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $25 a night to $1975 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 1703 of homes in Winter Park offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 662 rentals with pool or jacuzzi, or relax with the family in one of the 1445 homes with cable TV.

For all those dog lovers and cat lovers, Winter Park offers 151 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 12 rental sites in Winter Park where the top providers in that area are HomeAway, Booking.com, and TripAdvisor. There are 1155 HomeAway rentals, 348 Booking.com short term rentals and 237 TripAdvisor vacation rentals.