During the past 20 years, street vendors in various cities in the Global South have resisted aggressive state sanctioned removals and relocation strategies by organizing for vendors’ rights, protesting, and creating street vending member organizations with flexible relationships to the local state. Through these means, street vendors claim “rights in the city,” even as the bodies they inhabit and the spaces they produce are devalued by state legitimizing systems. In this article, I present a case study of the Union de Tianguistas y Comerciantes Ambulantes del Estado de Quintana Roo, a “bottom-up” driven, flexible street vending membership organization not formalized by the state in Cancún. I argue that the Union becomes a platform for street vendors to claim rights to the city, and exemplifies vending systems that combine economic activities with leisure spaces in marginalized urban areas, and circumvent strict vending regulations without being absorbed into or directly monitored by the state. Highlighting the Union’s sustainable practices of spatial transformation, and vision of self-managed spaces of socioeconomic urban life in Cancún, illuminates how the members of the Union claim rights to the city as an example of a process of awakening toward imagining possibilities for urban futures that moves away from the state and capitalists systems, and akin to what Lefebvre termed autogestion toward resisting neoliberal ideologies that currently dominate urban planning projects in the Global South.