A neglected area of study in adolescent development is family functioning in relation to adolescents’ sense of self and academic success. This study investigates students’ perceptions of their levels of family functioning (cohesiveness and adaptability) as it relates to their academic self-efficacy and school engagement, and answers the following questions: (1) Are there any significant differences in the academic self-efficacy beliefs and school engagement of Caribbean adolescents based on levels of family cohesion and family adaptability? (2) To what extent does the combination of family cohesion and family adaptability predict the academic self-efficacy and school engagement of Caribbean adolescents? Data were collected from a sample of 523 adolescents (197 males and 326 females) aged 17–19 years, enroled in postsecondary institutions in two Anglophone Caribbean countries (Barbados and St. Lucia). Results indicated that adolescents from families with balanced cohesion held significantly higher academic self-efficacy beliefs and school engagement levels than those from families with low cohesion. Regression analyses indicated that the family functioning model significantly predicted academic self-efficacy and school engagement. Interpretation of these results are discussed.