This study examined perceptions of adolescents regarding their parents’ behaviours such as guidance, punitiveness, monitoring and autonomy granting, and their influence on the development of adolescent self-esteem in Kenya. A standardized research instrument was used to gather data from a sample of 630 Kenyan high school students that ranged in age from 15 to 18 years and had a mean age of 16.3 years. The gender of these participants comprised of 35.7% males and 64.3% females. Standardized regression coefficients revealed that paternal guidance (ÿ = .204; p< .0001) was a stronger positive predictor of adolescents’ self-esteem compared to maternal guidance (ÿ =.164; p < .001). On the contrary maternal punitiveness (ÿ = -184; p<.01) was a stronger negative predictor of adolescent self-esteem than that of paternal punitiveness (ÿ = -124; p < .01). However, paternal monitoring (ÿ = 0.87; p> .05) and maternal monitoring (ÿ = 0.61; p> .05) were not significant predictors of Kenyan adolescents’ self-esteem. Furthermore results revealed that paternal autonomy granting (ÿ = -020; p >.05) was a negative, but insignificant predictor of Kenyan adolescents’ self-esteem, while the maternal autonomy granting (ÿ = 0.009; p> .05) had a positive but insignificant effect on adolescent self-esteem. The findings of this study may be useful for family life educators and family practitioners as they develop training materials on culturally relevant determinants of positive adolescent developmental outcomes.