Background: Antiretroviral therapy has minimized mother-to-child transmission of HIV and given hope to HIV-positive women considering pregnancy. In Jamaica, 36% of HIV-positive pregnant women enrolled in a pediatric/perinatal HIV/AIDS program had repeat pregnancies. Objective: To describe the epidemiology and identify factors associated with pregnancy after HIV diagnosis among HIV-positive women in Western Jamaica. Methods: A cross-sectional study was designed among HIV-positive women 18–54 years old who either had or did not have at least one pregnancy after HIV-positive diagnosis. A questionnaire was used to collect information on sociodemographic factors and health-seeking, reproductive, and sexual risk behaviors. Results: A total of 219 HIV-positive women participated in this study. Length of time since HIV diagnosis, CD4 count, and birth-control methods used were significant predictors of pregnancy after HIV diagnosis. Women diagnosed with HIV <5 years previously had lower odds for pregnancy after HIV diagnosis (adjusted OR 0.12, 95% CI 0.02–0.84) compared to those who had been diagnosed ≥8 years previously. Women with CD4 count <350 were over six times as likely to have a pregnancy after HIV diagnosis (adjusted OR 6.94, 95% CI 1.18–40.66). The odds for pregnancy after HIV diagnosis for a woman decreased by 93% if her children shared the same father (adjusted OR 0.07, 95% CI 0.006–0.77). Conclusion: This study identified significant predictors of pregnancy after HIV diagnosis that indicate that integrative family-planning interventions with supportive reproductive counseling are likely to help HIV-positive women obtain early appropriate care and plan the pregnancies they desire.