Collaborative consumption based on the sharing economy concept is no doubt becoming critical to the way people travel. Airbnb is a notable case to exhibit how online (P2P) platforms have helped individuals to rent out their extra living spaces to people from around the world. This study tried to understand the impact of the destinations’ characteristics on the price determinants of Airbnb and to find how the effects of the pricing factors vary according to the destinations’ characteristics using a hedonic pricing model. Two cities in the U.S. (i.e., New York and Miami) were selected to compare the effects of a destination’s characteristics on the Airbnb host’s pricing policy. Host reputation partially affect room rates in general, while transaction characteristics show relatively lower effects on prices. This study found several common factors affecting the price of Airbnb listings but also found unique factors for each destination.