Background: The aging of the population has increased the number of frail people living in long-term care facilities, underscoring the need for continuous updates in infectious diseases prevention strategies. The aim of this study was to analyze two pneumococcal disease outbreaks in elderly residences in Gipuzkoa, northern Spain, their impact on residents, and the containment measures implemented. Material and methods: The outbreaks took place in 2023 and in 2024 in two residences of 111 and of 155 residents, respectively. Diagnosis was based on clinical criteria, radiological findings, and microbiological techniques. Pneumococcal isolates were characterized by whole-genome sequencing. Results: The outbreaks involved five and six residents, respectively. Most residents in both facilities had been vaccinated with the pneumococcal polysaccharide 23-valent vaccine (PPV23) more than five years prior. The median attack rates were 4.5% and 3.9%, lower than those reported in similar outbreaks. The adopted infection transmission prevention measures successfully limited the spread of the outbreaks. Conclusions: PPV23 vaccination did not prevent invasive pneumococcal infection in the affected residents. The vaccination of elderly people living in long-term care facilities with 20-valent and 21-valent pneumococcal conjugated vaccines should be evaluated as a new preventive measure.