The first COVID-19 contagion wave caused unprecedented restraining measures worldwide. In Italy, a period of generalized lockdown involving home confinement of the entire population was imposed for almost two months (9 March–3 May 2020). The present is the most extensive investigation aimed to unravel the demographic, psychological, chronobiological, and work-related predictors of sleep disturbances throughout the pandemic emergency. A total of 13,989 Italians completed a web-based survey during the confinement period (25 March–3 May). We collected demographic and lockdown-related work changes information, and we evaluated sleep quality, insomnia and depression symptoms, chronotype, perceived stress, and anxiety using validated questionnaires. The majority of the respondents reported a negative impact of confinement on their sleep and a delayed sleep phase. We highlighted an alarming prevalence of sleep disturbances during the lockdown. Main predictors of sleep disturbances identified by regression models were: female gender, advanced age, being a healthcare worker, living in southern Italy, confinement duration, and a higher level of depression, stress, and anxiety. The evening chronotype emerged as a vulnerability factor, while morning-type individuals showed a lower predisposition to sleep and psychological problems. Finally, working from home was associated with less severe sleep disturbances. Besides confirming the role of specific demographic and psychological factors in developing sleep disorders during the COVID-19 pandemic, we propose that circadian typologies could react differently to a particular period of reduced social jetlag. Moreover, our results suggest that working from home could play a protective role against the development of sleep disturbances during the current pandemic emergency.