Homelessness has negative implications for mental well-being and quality of life. This paper identifies the quality of life variables that contribute to positive or negative wellbeing, reporting on a regression analysis from 343 individuals experiencing homelessness in Canada. Results indicate that a lack of sleep duration and quality reduced mental well-being for both genders, not having access to food and/or hygiene facilities decreased men’s well-being, and engaging in illegal subsistence strategies, such as selling drugs, negatively impacted women’s mental well-being. For persons experiencing homelessness, mental well-being and quality-of-life are gendered outcomes of their limited access to social determinants of health.