<i>Purpose</i> Prior studies reported homeless adolescents engage in more sexual risk than their housed peers. However, these comparisons are typically made post hoc by comparing homeless adolescent community-based samples with high school probability samples. This study uses a random sample of high school students to examine homelessness experiences and sexual risk behaviors. <i>Methods</i> A supplemental survey to the Youth Risk Behavior Survey containing questions regarding homelessness and sexual health was administered to Los Angeles high school students (N = 1,839). Multivariate logistic regressions assessed the associations between demographics, past year homelessness experiences (i.e., place of nighttime residence), and being sexually active and condom use at last intercourse. <i>Results</i> Homelessness experiences consisted of staying in a shelter (10.4%), a public place (10.1%), and with a stranger (5.6%). Lesbian, gay, bisexual, transgender, questioning (LGBTQ), younger, and male adolescents were more likely to experience homelessness. LGBTQ adolescents were also more likely to report staying with a stranger and less likely to report staying in a shelter. Compared to adolescents who stayed in shelters, adolescents who stayed with strangers and in public places were more likely to engage in unprotected sex at last intercourse. <i>Conclusions</i> Adolescents who report sexual activity and sexual risk taking are more likely to report homelessness experiences. With regard to sexual health, staying with strangers could be a particularly risky form of homelessness; LGBTQ and black adolescents are more likely to experience this form of homelessness. Efforts to reduce homelessness and sexual risk-taking need to recognize the specific vulnerabilities faced by these populations.