In 2008-2009, almost one million children experiencing homelessness were enrolled in school; this number has increased by 41% between 2009 and 2011. Unfortunately, this trend has continued to increase; according to the most recent data from the National Center for Homeless Education, the number of homeless students has reached a record of 1,056,794. These students are one of the most marginalized and victimized populations in schools. They experience more daily stressors and are more at risk than their housed peers. Unfortunately, there is a dearth in educational research about the conditions, within the school context, that promote resilience in this population that is highly at-risk. Using a conceptual framework that draws upon literature on educational risks, resilience, school structures, and school climate with respect to homeless students, this comparative qualitative case study investigated the protective factors offered by two school models for homeless students. The study compared the institutional structures, school climate, and experiences of students served by distinct types of programs: a traditional school and an alternative school designed specifically for homeless children and youth. By examining the impact of different school settings, the study contributes to a better understanding of the challenges, successes, and recommended research-based interventions designed to help a vulnerable student population. Findings suggest resilience-promoting protective factors recommended for a general student population apply to homeless students. Recommendations to schools interested in fostering resilience in their homeless population are provided