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The uncertainty of climate change’s impacts hinders adaptation actions, particularly micro-scale urban design interventions. This paper proposes a sixfold urban design framework to assess and enhance the resilience of urban form to climate change, where urban form refers to the patterns of streets, buildings, and land uses. The framework is then applied to Long Bay in Negril, Jamaica–a coastal area that incorporates the complex interactions between urbanization and a highly vulnerable socio-ecological system to climate change-related hazards, primarily sea-level rise. Empirical evidence from 19 in-depth interviews with planning and design professionals and development actors, in situ observations, and morphological analyses reveal that Long Bay’s current adaptation strategies heavily rely on bounce-back resilience measures that predominantly consider the impacts of extreme climatic events rather than slow-onset ones. Such strategies abet current tourism-driven development patterns while overlooking Long Bay’s inherent abilities for generative transformation and incremental changes to meet climatic uncertainty. Instead, this study’s findings highlight how generative urban form transformation would better equip Long Bay to cope with future uncertainty–climatic or other.