Over the past few years, great attention has been given to the impacts of the COVID-19 pandemic and its consequences on employee psychological well-being (PWB), particularly in the hospitality industry. Like many aspects of human life, employee PWB is influenced by multiple factors. One of the factors that may affect employee PWB is transformational leadership (TLS). Accordingly, we aim through this study to empirically (1) examine the direct effect of transformational leadership on employee PWB and (2) investigate the potential independent and serial mediation effects of employee engagement (EEG) and job satisfaction (JS) on the TLS-PWB relationship after the height of the COVID-19 pandemic. Data were gathered using an online questionnaire from a convenience sample of 403 front-line employees from five-star hotels in Saudi Arabia. The partial least squares structural equation modeling (PLS-SEM) with the bootstrapping technique was utilized to test the study hypotheses. Based on the demands–resources (JD-R) theory, the findings of this study reveal a significant positive effect of TLS on hotel employees’ PWB. Additionally, drawing on the stimulus–organism–response (S-O-R) model, the two main contributions of this study are: (1) EEG and JS serially and independently have a significant partial mediational effect on the TLS-PWB relationship among hotel employees, and (2) EEG has a greater impact on the TLS-PWB relationship as an intervening variable than the two other mediators (JS, as well as EEG and JS serially). Based on these findings, hotel management should mainly consider developing and encouraging TLS behavior among their managers to promote EEG and increase JS among their followers, which consequently enhances their PWB and alleviates negative psychological outcomes due to experiencing a disaster such as the COVID-19 pandemic.