In Canada, approximately 150,000 youth live on the street. Street-involvement and homelessness have been associated with various health risks, including increased substance use, blood-borne infections and sexually transmitted diseases. We undertook a qualitative study to better understand the social and structural barriers street-involved youth who use illicit drugs encounter when seeking housing. We conducted 38 semi-structured interviews with street-involved youth in Vancouver, Canada from May to October 2008. Interviewees were recruited from the At-risk Youth Study (ARYS) cohort, which follows youth aged 14 to 26 who have experience with illicit drug use. All interviews were thematically analyzed, with particular emphasis on participants' perspectives regarding their housing situation and their experiences seeking housing. Many street-involved youth reported feeling unsupported in their efforts to find housing. For the majority of youth, existing abstinence-focused shelters did not constitute a viable option and, as a result, many felt excluded from these facilities. Many youth identified inflexible shelter rules and a lack of privacy as outweighing the benefits of sleeping indoors. Single-room occupancy hotels (SROs) were reported to be the only affordable housing options, as many landlords would not rent to youth on welfare. Many youth reported resisting moving to SROs as they viewed them as unsafe and as giving up hope for a return to mainstream society. The findings of the present study shed light on the social and structural barriers street-involved youth face in attaining housing and challenge the popular view of youth homelessness constituting a lifestyle choice. Our findings point to the need for housing strategies that include safe, low threshold, harm reduction focused housing options for youth who engage in illicit substance use.