The purpose of this study is to analyze the effects of parenting attitudes and mediating variables (self-esteem, social support) on psychological well-being of perceived vocational high school students. For this purpose, 382 students of vocational high schools in four universities including Daejeon metropolitan city and three schools in Chungcheongnam-do were included in the analysis. Data were processed using SPSS 21.0 and AMOS 21.0 programs. The main results are as follows. First, the relationship between independent parenting attitude and parental psychological well-being was found to have significant influence. Second, the relationship between parenting attitude and psychological well-being mediated through self-esteem showed a significant influence on parenting attitude and self- esteem. In addition, it was found that there was a significant influence between self-esteem and psychological well-being. Third, in the relationship between parenting attitude and psychological well-being mediated by social support, there was a significant influence between parenting attitude and social support. In addition, it was confirmed that there is a negative influence between social support and psychological well-being. Based on the results of this study, we have discussed with previous research. In conclusion, the implications for improvement of psychological well-being of vocational high school students were suggested.