The objective of this study was to determine the prevalence of depressive symptoms in Jamaican adolescents and examine its association with individual and family factors. We used an abbreviated form of the Beck's Depression Inventory II (BDI-II) to assess depressive symptoms among 748 students, attending public high schools in the parish of Hanover Jamaica. In the analysis, we classified adolescents with scores in the upper quartile of the depressive symptom score as having depressive symptoms. Multivariate logistic regression was used to determine the predictors of depressive symptoms. 14.2% of participants reported depressive symptoms. There was association between engagement in sexual activity [Odds Ratio (OR) = 1.61, 95% Confidence Interval (CI) = 1.02-2.51], parental monitoring of adolescent activity (OR=2.04, 95%CI=1.33 -3.12), maternal affection and support (OR= 4.07, 95%CI= 2.62-6.33), and paternal affection and support (OR= 1.58, 95%CI= 1.05-2.39) with self reported depressive symptoms at the bivariate level. In the final model, depressive symptoms was associated with perceived lack of maternal affection and support (OR= 4.06, 95%CI= 2.61-6.32) and showed marginal association with being sexually experienced (OR= 1.59, 95%CI= 1.00-2.52). As most homes are female-headed, establishing support systems for the mother to take care of their adolescent children may decrease the odds of depressive symptoms. Sexually experienced adolescents may require screening for depression. Further research is required to fully explore all factors that could predispose Jamaican adolescents to depression. ©2007 with author. Published by TheScientificWorld.