Urban vegetation can mitigate increases in summer air temperature by reducing the solar gain received by buildings. To quantify the temperature-moderating influence of city trees and vine-covered buildings, a total of 13 pairs of temperature loggers were installed on the surfaces of eight buildings in downtown Toronto, Canada, for 6 months during the summer of 2008. One logger in each pair was shaded by vegetation while the other measured built surface temperature in full sunlight. We investigated the temperature-moderating benefits of solitary mature trees, clusters of trees, and perennial vines using a linear-mixed model and a multiple regression analysis of degree hour difference. We then assessed the temperature-moderating effect of leaf area, plant size and proximity to building, and plant location relative to solar path. During a period of high solar intensity, we measured an average temperature differential of 11.7 °C, with as many as 10-12 h of sustained cooler built surface temperatures. Vegetation on the west-facing aspect of built structures provided the greatest temperature moderation, with maximum benefit (peak temperature difference) occurring late in the afternoon. Large mature trees growing within 5 m of buildings showed the greatest ability to moderate built surface temperature, with those growing in clusters delivering limited additional benefit compared with isolated trees. Perennial vines proved as effective as trees at moderating rise in built surface temperature to the south and west sides of buildings, providing an attractive alternative to shade trees where soil volume and space are limited.