Background Studies on political ideology and health have found associations between individual ideology and health as well as between ecological measures of political ideology and health. Individual ideology and aggregate measures such as political regimes, however, were never examined simultaneously. Methodology/Principal Findings Using adjusted logistic multilevel models to analyze data on individuals from 29 European countries and Israel, we found that individual ideology and political regime are independently associated with self-rated health. Individuals with rightwing ideologies report better health than leftwing individuals. Respondents from Eastern Europe and former Soviet republics report poorer health than individuals from social democratic, liberal, Christian conservative, and former Mediterranean dictatorship countries. In contrast to individual ideology and political regimes, country level aggregations of individual ideology are not related to reporting poor health. Conclusions/Significance This study shows that although both individual political ideology and contextual political regime are independently associated with individuals' self-rated health, individual political ideology appears to be more strongly associated with self-rated health than political regime.