Cities around the globe are breaking their heads on how to respond to Airbnb and other short-term rental platforms. And even though this player has been in the field for over a decade now, cities are still struggling with the question: what to do with Airbnb and how to regulate? But what is it that they are struggling with exactly? And why is regulating so hard? These and other questions will be answered in this article that is a short version of my earlier published article in Current Issues in Tourism.