Influenza epidemics pose a great overload over health-care facilities with an increase in the burden of disease for patients and healthcare costs. Despite a well-established amount of research in the area, vaccination rates show room for improvement and more research is needed in finding systematic interventions useful in improving healthcare workers (HCWs) vaccination coverage (VC). The purpose of this study was to describe the self-reported frequency of influenza immunization in HCWs and to identify demographic, socioeconomic, lifestyle, and health factors associated with this practice in Italy. Data about 5823 workers participating in the Italian national survey about health and healthcare services utilization are analyzed in the present study. Overall, 18.8% of HCWs reported being vaccinated against seasonal flu. In the multilevel regression, older workers had a higher likelihood of vaccine uptake (OR: 6.07; 95% CI 4.72–7.79), similar to those with chronic conditions or poor self-perceived health status (OR: 2.18 95% CI 1.17–4.09). On the other hand, the results highlighted a lower rate of VC in female HCWs (OR: 0.73 95% CI 0.61–0.86). Data confirm the low compliance towards flu immunization among Italian HCWs and highlight an important gap to be investigated in women.