Objective and subjective health generally have a positive relationship, although their association may be moderated by factors such as gender and personality. We aimed to analyze the association between personality and objective (metabolic syndrome (MetS)) and subjective-physical health in older men and women. For this purpose, in 138 participants (53.6% women, Mage = 66.85), neuroticism, conscientiousness, extraversion, openness, and agreeableness (NEO Five Factor Inventory), subjective-physical health (Short Form Health Survey, SF-36), and MetS (employing waist circumference, blood pressure, triglycerides, high-density lipoprotein cholesterol, and glycated hemoglobin) were assessed. Logistic regression analysis was performed to analyze whether personality was associated with MetS. Moreover, hierarchical regression analyses were conducted to analyze the relationship between personality or MetS, and subjective-physical health. Finally, gender and personality moderation analyses were performed with PROCESS. Results showed that higher neuroticism was associated with an increased likelihood of MetS, whereas higher neuroticism and lower extraversion were associated with lower subjective-physical health. Moreover, the negative relationship between MetS and subjective-physical health was stronger in individuals with low conscientiousness. Regarding gender differences, only in women, higher extraversion was related to a decreased likelihood of MetS, and MetS was related to lower subjective-physical health. In conclusion, higher neuroticism is the main vulnerability health factor, whereas to a lesser extent extraversion and conscientiousness are protective factors. Furthermore, the association between objective and subjective health is not direct, but it may vary depending on personality and gender.