Introduction: Sleep disorders have been reported in individuals living with HIV (PLWH), with a prevalence rate of over 50%. The main risk factors contributing to the development of sleep disturbances are not yet fully understood. We investigate the prevalence and risk factors associated with poor sleep quality in a population of PLWH who are receiving antiretroviral therapy (ART). Methods: The Pittsburgh Sleep Quality Index (PSQI) was used to evaluate sleep quality in PLWH attending our HIV Outpatient Clinic between October 2022 and April 2023. All subjects with a PSQI score > 5 were considered bad sleepers. A logistic regression analysis was carried out to assess risk factors associated with a PSQI score > 5. Results: A total of 132 PLWH (78% males) who received ART for at least one month were included in this observational study. The median age was 56 (IQR 47–61). Among all, 41 (31%) had a history of AIDS, and 95 (72%) were receiving an INSTI-based ART. The study population was divided into two groups: PSQI ≤ 5 (90; 68.2%) and PSQI > 5 (42; 31.8%). A lower BMI and the use of bictegravir in the current ART were associated with a PSQI score ≤ 5. In the multivariate analysis, the use of a bictegravir-based ART remained the only factor associated with better sleep quality (OR 0.17; p = 0.0222). No further associations between sleep disturbances and other epidemiological and clinical features were found. Conclusion: In this real-life scenario, poor sleep quality was observed in 31% of the cases, primarily among individuals with higher BMI. In addition, bictegravir users might seem to have a lower likelihood of experiencing poor sleep quality.