A warming climate, increasing frequency and severity of extreme heat events, and the heat island effect are cumulatively expected to exacerbate climate thermal loading on urban buildings. This in turn could lead to increased summertime overheating risk, with any active means for addressing this likely to influence future energy consumption and CO2 emission patterns. This paper examines how the microclimatic loading presented by the heat island (UHI) effect influences summertime adaptive comfort in traditional urban residential buildings. The method for addressing this utilises the novel approach of coupling a computationally efficient urban climate model with an established building energy model to simulate a residential street canyon within the London heat island. Key findings highlighted adaptive capabilities to achieve summertime ‘comfort’ in most rooms without the need for energy intensive mechanical cooling. The alternative of using indiscriminate and widespread mechanical cooling within the canyon length is estimated to result in a 0.4 K increase in nocturnal canyon temperatures, and an additional 4.4% of CO2 released to the climate. In contrast, a targeted approach of cooling rooms where adaptive capacity is insufficient more than halves the canyon CO2 emission estimate; which in turn highlights the necessity for detailed overheating assessments in managing energy use in such traditional residential neighbourhoods within UHIs.