This chapter reflects on the production of Orlando, Florida and how the prevailing vision of its downtown development reiterates the enduring legacy of settler colonialism through its anti-homeless policies. These policies manifest as ugly laws, laws designed to define the unsightly and unwanted bodies of the citizenry in order to keep them from view. These laws are presented simultaneously as concerning aesthetics, safety issues, and even charity, while also serving the enduring settler colonial power structures that first shaped and sanctioned the state of Florida. The focus for analysis is the existing policies that regulate the downtown district of Orlando. These policies exhibit many of the characteristics that Susan Schweik identifies in the ugly laws, particularly with regard to the social, textual, and performative contexts in which the laws are deployed. Ultimately, this analysis denaturalizes downtown space in order to disrupt notions of white settler innocence and neutrality of space. The chapter demonstrates how Orlando’s strategies of city regulation are used to ensure the absence of ugliness, and how these techniques are deployed to maintain the dominance of both settler colonialism and the dynamics between settler society and ableism.