Though housing inequality is manifest in a variety of ways around the world, one of the most noteworthy has been the rise of short-term rentals. And while a growing body of literature has demonstrated the negative impacts of this new housing typology on cities and neighborhoods, as well as the need for such cities to regulate this phenomenon, scholars have had less to say about how the fights for and against these regulations have actually played out. Through a case study of proposed short-term rental regulations in the small southern college town of Starkville, Mississippi, this paper documents some of the key ways that fights over short-term rental regulation actually play out on the ground, and how these dynamics can lead to more effective approaches to regulating short-term rentals in the future.