This study investigates the role of property quality in shaping booking intentions within the dynamic landscape of the hospitality sector. A comprehensive approach, integrating qualitative and quantitative methodologies, is employed, utilising Airdna’s dataset spanning from July 2016 to June 2020. Multiple regression models, including interaction terms, are applied to scrutinise the moderating role of property quality. The study unveils unexpected findings, particularly a counterintuitive negative correlation between property quality and booking intentions in Model 7, challenging conventional assumptions. Theoretical implications call for a deeper exploration of contextual nuances and psychological intricacies influencing guest preferences, urging a re-evaluation of established models within hospitality management. On a practical note, the study emphasises the significance of continuous quality improvement and dynamic strategies aligned with evolving consumer expectations. The unexpected correlation prompts a shift towards more context-specific approaches in understanding and managing guest behavior, offering valuable insights for both academia and the ever-evolving landscape of the hospitality industry.