Jamaica has had over 200 floods in the past 50 years, causing significant human and economic losses. Kingston has often caused the most damage due to its high population density and capital exposure. Kingston is crucial to the country’s socio-economic stability, and climate change is increasing flood risk, but a local-scale assessment of its flood risk is unavailable. This study fills this gap in the literature by using two models of the integrated Valuation of Ecosystem Services and Tradeoffs (inVEST) suite to qualitatively assess Kingston metropolitan pluvial and coastal flood risk. Key locations like Kingston Container Terminal and downtown Kingston are at high coastal flood risk, according to the results. The study also shows that sea level rise (117%) and habitat loss (104%) will increase the highly exposed area. Instead of hard-engineering coastal protection, this study suggests investing in nature-based and ecoengineering solutions to improve coastal resilience and ecosystem services. The urban flood assessment finds downtown, particularly the Mountview and Minor catchments, at high risk due to poor runoff retention and high population density. To fully address downtown pluvial flood risk, structural social reforms are needed. To reduce short-term flood risk, local authorities should consider targeted adaptation measures. These may include maintaining the drainage gully system and reducing surface runoff in uphill downtown areas. Thus, this study seeks to inform Kingston urban planners about risk distribution and suggest adaptation measures to improve flood resilience.