Although a large part of the world’s workforce engaged in mandatory Work from Home during the COVID-19 pandemic, the experience was not the same for everyone. This study explores whether different groups of employees, based on their work and organizational characteristics (i.e., organizational size, number of days per week working from home, working in team) and personal characteristics (i.e., remote work experience, having children at home), express different beliefs about working remotely, acceptance of the technology necessary to Work from Home, and well-being. A study was conducted with 163 Italian workers who answered an online questionnaire from November 2020 to January 2021. A cluster analysis revealed that work, organizational, and personal variables distinguish five different types of workers. ANOVA statistics showed that remote workers from big companies who worked remotely several days a week, had experience (because they worked remotely before the national lockdowns), and worked in a team, had more positive beliefs about working remotely, higher technology acceptance, and better coping strategies, compared to the other groups of workers. Practical implications to support institutional and organizational decision-makers and HR managers to promote remote work and employee well-being are presented.