Find the best Winter Park vacation rentals on Tripping.com. With over 1925 home rentals, take your pick from a wide variety of choices including studio apartments, luxury condos, and cozy cabin rentals. Prices in Winter Park range from $50 a night. Many rentals can also be booked directly online.Vacation home rentals found on Tripping.com offer more amenities than the average hotel room along with many of the comforts of home. Going on a business trip or need to stay connected? 1667 homes in Winter Park offer high-speed WiFi Internet so you won’t miss a beat. Travelling with kids? Let them splash around in any of the 579 rentals with pool or jacuzzi, or relax with the family in one of the 1568 homes with cable TV.For all those pet owners with dogs or cats, Winter Park offers 165 pet-friendly vacation rentals for your extended family. Find the perfect vacation rental that matches your budget and style on Tripping.com.Search properties from 10 vacation rental sites in Winter Park where the top providers in that area are HomeAway, Expedia, and TripAdvisor. There are 966 HomeAway rentals, 380 Expedia short term rentals and 286 TripAdvisor vacation rentals.