Islands tend to conjure images of tourist beaches or rural peripherality. They rarely figure into the urban studies literature as theoretically generative spaces that can potentially reinvigorate urban knowledge production. In empirical terms, urban studies mainly foreground inland spaces and barely represent the nature of coastal cities such as island cultures, increasing watermark on the coast, and urban island mobility patterns. Attending postcolonial provocations that advocate for urban theorization beyond the usual Anglo-American context, I interrogate the urban-rural interface of island cities. In particular, I foreground the various urban expressions reshaping island dynamics using a case study in the Philippines— gender dynamics of transnational island urbanism. I respond to the session on Tropical and island urbanism: Emerging urban theories and narratives in tropical and island contexts by moving the discussions on urban political contestations beyond the urban-rural binary. We argue, rather, that those labelled as urban and rural areas are mutually reinforcing spaces of island urbanism.