People living with HIV (PLWH) are a heterogeneous group of immunocompromised persons, yet underrepresented in randomized clinical trials leading to vaccination registration. Detectable HIV viral load and having chronic comorbidities may increase the risk of severe COVID-19 outcomes in this group of patients. We aimed to assess the efficacy and safety of vaccinations against COVID-19 in PLWH. Materials and Methods: We performed a retrospective analysis of medical records of HIV-positive individuals routinely followed up between 1st January 2021 and 30 April 2022 that were at the HIV Outpatient Clinic in Warsaw. The analysis included data on the type and date of administration of subsequent doses of COVID-19 vaccination, adverse vaccine reactions, and the history of SARS-CoV-2 infection. Results: In total, 217 patients were included in the analysis, with a median age of 43 years (IQR: 35.5–51.5 years) and median CD4+ count of 591 cells/uL (IQR: 459.5–745.0 cells/uL). Most of the patients were male (191/217, 88.0%) and were vaccinated with the BNT162b2 vaccine (143/217, 65.9%). None of the patients diagnosed with COVID-19 required hospitalization. Vaccine adverse events (VAE) mostly occurred after the 1st dose (in 33/217 (15.2%)), and none of them were severe or required medical care. Conclusions: In our cohort of patients, vaccination against COVID-19 proved to be safe and effective against a severe course of the disease among people living with HIV. However, vaccination, to a lesser degree, protects against mild SARS-CoV-2 infection. Longer observations are required in order to assess the sustainability of protection against severe COVID-19 in this group of patients.