Calor, InêsMagarotto, Mateus2023-07-292023-07-292019978-88-99243-93-7https://hdl.handle.net/20.500.14235/424Short-term rental platforms, especially Airbnb, represent a deep change in the housing sector. In Portugal, the first attempts at designing regulatory measures to balance short-term rental are far from achieving high levels of compliance. As in other European cities, the monitoring and enforcement of rules drawn up so far entail difficulties for most of the management entities. This paper aims to discuss the relationship between the type of rules designed for short-term rentals, and the enforcement effort required from public entities. The methodology relies on a brief analysis of the rules implemented in different European cities through available literature, and a detailed assessment on the evolution on the Portuguese case, evaluating the expectations on the level of compliance with short term planning rules. To access enforcement effort, we propose a systematization of the type of rules in place in the main European cities. In countries with traditionally low levels of compliance and reduced enforcement results (such as Portugal), reducing the enforcement effort seems the ‘smart’ thing to do. We conclude that monitoring and enforcement of short-term rental rules is not a ‘mission impossible’ but it is certainly a demanding one.enAirbnbShort-term rentalHousingTourismIllegal developmentArticle2868-2877