While estimating homelessness in Canada has been difficult, it is believed at least 200,000 Canadians experience homelessness each year. What is often missing from research into homelessness in Canada is identification of the specific situations and needs of women experiencing homelessness. This paper identifies the complexity and specific issues for women experiencing homelessness, and presents two different supportive housing models offered by the Jean Tweed Centre in Toronto as responsive models to the needs of women. The two housing models discussed serve women experiencing homelessness and concurrent mental health, and/or substance use concerns.