The study aimed to explore the mediating role of strategic flexibility and its four dimensions (coordination flexibility, production flexibility, marketing flexibility, and human resources flexibility) in the relationship between digital leadership and organizational ambidexterity in travel agencies in the Kingdom of Saudi Arabia. The descriptive analytical approach and questionnaire were used to collect data from the study sample, which consisted of managers and supervisors in these agencies. The analysis of 422 valid questionnaires was based on using appropriate statistical tests to verify the study objectives and hypotheses. The results showed a statistically significant positive effect of digital leadership on organizational ambidexterity, strategic flexibility, and its four dimensions. The results also showed a statistically significant positive effect of strategic flexibility and its dimensions on organizational ambidexterity. The results also showed that strategic flexibility, the production flexibility, and marketing flexibility played partial mediating roles, while the coordination flexibility and human resources flexibility played complete mediating roles in the relationship between digital leadership and organizational ambidexterity in travel agencies.