Individuals working in the sex industry continue to experience many negative health outcomes. As such, disentangling the factors shaping poor health access remains a critical public health priority. Within a quasi-criminalised prostitution environment, this study aimed to evaluate the prevalence of occupational stigma associated with sex work and its relationship to barriers to accessing health services. Analyses draw on baseline questionnaire data from a community-based cohort of women in street-based sex work in Vancouver, Canada (2006-2008). Of a total of 252 women, 141 (55.9%) reported occupational sex work stigma (defined as hiding occupational sex work status from family, friends and/or home community), while 125 (49.6%) reported barriers to accessing health services in the previous six months. In multivariable analysis, adjusting for sociodemographic, interpersonal and work environment risks, occupational sex work stigma remained independently associated with an elevated likelihood of experiencing barriers to health access. Study findings indicate the critical need for policy and societal shifts in views of sex work as a legitimate occupation, combined with improved access to innovative, accessible and non-judgmental health care delivery models for street-based sex workers that include the direct involvement of sex workers in development and implementation.