The aim of this study was to investigate the associations between sibling history, parental history and simultaneous sibling and parental history of diabetes, and the presence of the metabolic syndrome (MetS) and its components. Our study comprised 5000 participants from Taiwan Biobank until April, 2014. The participants were stratified into four groups according to sibling and/or parental family history (FH) of DM. MetS was defined as having 3 of the following 5 abnormalities based on the standard of the NCEP ATP III and modified criteria for Asians. The prevalence of MetS and its traits was estimated and compared among the four familial risk strata. Multivariate logistic regression analysis showed participants with sibling FH of DM [vs. no FH of DM; odds ratio (OR) 1.815; 95% confidence interval (CI) 1.293 to 2.548; p = 0.001], participants with parental FH of DM (vs. no FH of DM; OR 1.771; 95% CI 1.468 to 2.135; p < 0.001), and participants with simultaneous sibling and parental FH of DM (vs. no FH of DM; OR 2.961; 95% CI 2.108 to 4.161; p < 0.001) were significantly associated with MetS. A synergistic effect of sibling FH of DM and parental FH of DM on the association of MetS was also observed. In a nationally representative sample of Taiwan adults, a simultaneous sibling and parental history of diabetes shows a significant, independent association with MetS and its components, except for abdominal obesity. The association highlights the importance of obtaining stratified FH information in clinical practice and may help to identify individuals who should be targeted for screening and early prevention of MetS.