The current competitive scenario is fast-moving toward an integration of sophisticated technological innovations, i.e. smart solutions, for hospitality, in particular the accommodation industry. Internet of Things (IoT) technologies are able to connect and let communicate different devices to craft a personalized customer experience. Given the undeniable impact for the hospitality sector, the decisions about adopting smart solutions is not always linear: benefits and limitations co-exist and need to be weighed against each other. By adopting a fuzzy-set Qualitative Comparative Analysis, this paper compares several decision-making factors that may influence the willingness to adopt IoT, surveying owners/managers in the Greek accommodation industry. Results show four sufficient solutions and the relative configurations: (i) a weighted evaluation of risks and opportunities; (ii) benefits to gain a competitive advantage; (iii) risks and barriers to innovate; and (iv) future technological necessities related to the increasing digitalization. An accurate discussion of theoretical and managerial implications is built upon these solutions.