The rapid growth of the urban population and the increasing densification of the built environment have led to a significant rise in urban air temperatures compared to rural areas, a phenomenon known as the urban heat island. During summer, this urban warming drives energy demand for cooling, as buildings strive to maintain comfortable indoor temperatures. Building Integrated Vegetation Technologies (BIVTs), such as green roofs and green walls, can mitigate extreme summer temperatures in urban environments and influence building energy use to varying extents, depending on the geometric characteristics of the buildings and the specific BIVT applied. This study investigates the effects of green roof-, green façade-, and living wall-based scenarios on urban air temperatures, aiming to identify which BIVT is most effective in reducing urban overheating under different conditions. Additionally, the study evaluates the potential of these BIVTs to influence building energy consumption. The research focuses on three Mediterranean cities: Rome, Bari, and Florence. Within these cities, urban areas with distinct building arrangements—scattered, arrayed, and enclosed—were selected to broaden the applicability of the findings. The urban areas share a similar background climate (Csa) according to the Köppen-Geiger classification. Two hundred and eighty-one BIVT-based scenarios were developed and modeled using ENVI-met software to explore which technologies and configurations offer the greatest urban air temperature reductions. Furthermore, the impact of BIVTs on building energy use was evaluated using EnergyPlus software. The results of this study will provide valuable insights into the most promising BIVTs for enhancing urban and building sustainability.