An in-depth look into the mechanics of short term rentals in Italy. The study is based on a vast dataset comprising of all the properties listed on the Airbnb website in 10 major cities in the years 2015, 2016 and 2017. We discuss the spatial patterns of Airbnb supply and demand within and between cities, we then hypothesize on the possible drivers of the Airbnb offer and suggest a possible way to assess whether Airbnb supply could be driven by an economic advantage of short-term over long term letting. We also discuss the way the benefits of this particular incarnation of the sharing economy are shared among participants. Finally, we conclude by presenting a possible alternative way of regulating Airbnb.