Save hundreds with a vacation home rental from Tripping.com and forget the hotel room. For the ultimate getaway, Winter Park offers 1650 affordable vacation rentals with a price to match your budget and accommodation needs. Prices in Winter Park start at an average price of $265 a night with long-term rentals averaging $13010 a month.These vacation rentals offer a range of amenities, so you’ll feel right at home. For those looking to stay in a corporate rental, 1465 of Winter Park’s rentals offer high speed WiFi Internet so you can easily keep in touch with your company or team. Go for a swim at one of the 477 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 1415 vacation home rentals.Traveling with your dog or cat? Choose from 122 pet-friendly rentals in Winter Park that allow you to bring your extended family along.Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your pets. Many properties allow you to book directly online, so once you find that perfect vacation rental, you’ll be all set to go!Search properties from 11 vacation rental sites in Winter Park where the top providers in that area are HomeAway, Expedia, and TripAdvisor. There are 850 HomeAway rentals, 275 Expedia short term rentals and 224 TripAdvisor vacation rentals.