The fostering of resilience in young people is based on a variety of social, cultural, and political factors that impact their interactions with and in the community. Through analysis of life history narratives of young women experiencing homelessness, this research links resilience not to traits inherent in individual young people, but to sustained social support. We emphasize the importance of key familial relationships as they relate to the development of resilience in young people. This research shows that positive connections within family, broadly defined to include families of choice and extended family networks, are vital to supporting young people experiencing homelessness. We also pay particular attention to the implications of family and resilience in the lives of Aboriginal young women experiencing homelessness, recognizing the significance of decolonization, cultural identity, and Indigenous world views in the success and stability of Aboriginal young people. This article argues that policy approaches to youth homelessness should address and eradicate policies that have a history of perpetuating culture erasure and the continuation of colonization. In order to enhance resilience, youth require a multi-systemic approach that provides support in the form of family reconnection, which acknowledges and respects a broader definition of family, moving beyond the nuclear family to extended family members, families of choice, and supportive communities.