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Youth homelessness represents a persistent and significant challenge for service sectors with limited best practice guidance. Housing supports, in particular, are widely deployed, with the practice-oriented literature providing little detail regarding service design beyond broad domains such as employment support and life skills coaching. The present multiple case study investigation was designed to develop a preliminary understanding of the guiding principles that attend the development of interventions that support youth exiting homelessness in the Canadian context. These case studies were conducted with a diverse group of five organizations recognized as sector leaders, with findings considered in light of practice standards from the better-established adult housing literature. Key findings with respect to service models included the strategies used to provide flexible, culturally responsive, tailored services with an emphasis on specialist support. Implementation factors included the navigation of strategic partnerships, the use of data in capacity-building, and the benefits and drawbacks of larger, centralized service environments versus smaller, dispersed environments. Youth-specific considerations in housing stabilization models are highlighted. This work contributes to a growing body of literature that seeks to articulate best practices in the effort to address and prevent youth homelessness.