Despite advances in diagnosis, antimicrobial therapy and supportive care modalities, community-acquired pneumonia (CAP) remains an important cause of morbidity and mortality, especially in patients who require hospitalization. Elderly patients with poor functional status are characterized by a higher risk of developing severe CAP, due to the frequent presence of underlying respiratory and cardiac diseases, alteration of mental status, and immunosuppression. In recent years, changes in the healthcare system have shifted a considerable part of older patient care from hospitals to the community, and the traditional distinction between community- and hospital-acquired infections has become less clear. Pneumonia occurring among outpatients in contact with the healthcare system has been termed healthcare-associated pneumonia. Older frail patients have a high frequency of aspiration pneumonia and pneumonia due to gram-negative bacilli and other multidrug resistant pathogens. The contemporary presence of renal impairment usually requires specific dose adjustment of antibiotic therapy, which may be toxic in this specific patient population. This review produces a summary of therapeutic recommendations on the basis of the most updated clinical and pharmacological data.