Tourism-dependent small island states face escalating climate, health, and environmental risks alongside simultaneous rapid growth in the largely unregulated short-term rental market through platforms like Airbnb. This study introduces and applies a novel Climate–Health–Environment (CHE) Index, alongside a Property Quality Index (PQI), to assess the spatial distribution of vulnerability and market performance across Airbnb listings in Jamaica. Integrating geospatial risk data with property-level metrics, we reveal a critical misalignment where systemically vulnerable properties continue achieving high occupancy and pricing, driven by aesthetics and branding rather than resilience. While PQI is the strongest predictor of guest satisfaction and price, the CHE Index illuminates hidden exposure patterns and offers practical utility for policy intervention. Findings underscore the urgent need for regulatory frameworks that align market behavior with risk-aware development. This research contributes a new empirical tool for resilience assessment and informs governance strategies for sustainable tourism in climate-vulnerable small island economies.