Supportive housing (SH), largely consisting of Transitional Living Programs (TLPs) and Permanent Supportive Housing (PSH), is the primarly intervention being applied to the one-in-ten young adults that experience homelessness in the United States each year. To date, efforts to understand the perception of these programs among young adult tenants have focused singularly on TLPs or PSH. The current qualitative study builds upon previous evidence through a comparative analysis of young adult perceptions of TLPs and PSH and examines the the physical, social, and service environments associated with each program. Results suggest six themes, including three themes focused on factors associated with location, common to both TLPs and PSH: desired proximity to friends, family, and amenities; wanted distance from negative influences; and increased ability to assimilate. Three additional themes focused on the environment internal to the housing program that differentiated the models: shared space with roommates, the service environment and relationships with SH staff, and the moving on process. Findings indicate that location is an important but complex element of the housing environment for all young SH tenants with both positive and negative factors. Within the housing environment, more TLP residents had roommates and spoke of utilizing the services associated with their housing, but discussed feeling less prepared for life after SH.