Background and Objectives: Infectious disease outbreaks are a major challenge for public health systems worldwide, especially for healthcare workers (HCWs). Taif city, in Saudi Arabia, has a high population density and is a tourist destination, which puts it at a high risk of infectious disease outbreaks. Despite its geographical importance, no previous study has been conducted that focuses on assessing the preparedness of healthcare workers in Taif city for managing infectious disease outbreaks. Therefore, we aimed to assess the overall level of preparedness among HCWs in healthcare facilities across Taif city and identify the challenges they face when managing infectious disease outbreaks. Materials and Methods: We conducted a cross-sectional study from October to December 2024 among 294 healthcare workers, using a structured questionnaire. We assessed the sociodemographic characteristics, infection prevention and control (IPC) training received by HCWs, the level of preparedness for managing infectious disease outbreaks, and their level of knowledge (low, moderate, or high). The association between sociodemographic characteristics and knowledge from having received IPC training and the level of preparedness was assessed using binary logistic regression. A p-value of ≤ 0.05 was considered as significant. Results: Around 31.7% of the participants were aged 31–40 years, with 59.2% of them being female. Among the HCWs we assessed, 44.6% were nurses and 31.3% of the HCWs were from hospitals with a bed capacity of over 500. Only 16.3% of HCWs felt fully prepared on a personal level and only 20.7% believed their facility was fully prepared for managing an outbreak. A low level of knowledge was reported among 71.8% of the participants. The odds of having received IPC training were significantly higher among HCWs aged 41–50 years (AOR = 15.7; 95% CI = 4.26–58.1), for those working in the inpatient department (AOR = 6.3; 95% CI = 1.46–27.05), and for those with a moderate level of knowledge (AOR = 0.12; 95% CI = 0.03–0.5). The odds of being fully prepared for an infectious disease outbreak were significantly higher for males (AOR = 2.58; 95% CI = 1.18–5.63) and those working in the in-patient department (AOR = 6.87; 95% CI = 1.7–27.8) and significantly lower for those with a low level of knowledge (AOR = 0.19; 95% CI = 0.06–0.61). Conclusion: Even though many HCWs have undergone IPC training, our findings highlight gaps in both knowledge and overall preparedness among healthcare workers in Taif city. Regular refresher courses, improved resource allocation, and implementing scenario-based emergency drills may help in improving the overall knowledge and preparedness of HCWs.