An urban heat island (UHI) effect is a phenomenon that occurs when urban areas experience higher temperature than their surrounding rural areas. This contributes to global warming, risk of heat-related mortalities and unpredictable thermal conditions. Therefore, gaining insights into the knowledge of resilience and adaptation against adverse urban heat effects contribute to the development of sustainable cities. This chapter presents three case studies focusing on the contemporary Australian experience in mitigating UHI effects and thermal discomfort at regional, city and local scales. The case studies are based on satellite imagery, in-situ observations and community engagement to deliver a comprehensive understanding of the contemporary efforts to reduce the effect of urban heat. On the regional scale, the role of strategic urban planning and related infill development policy on spatial variation of UHI was examined. This was conducted through diurnal and nocturnal Moderate Resolution Imaging Spectroradiometer (MODIS) imageries in South East Queensland between 2005 and 2018. Subsequently, this chapter describes an innovative approach to integrate geospatial data and community opinions on urban greening and community shade to develop a shade mapping and (walking) route comfort model for the city as an adaptation approach to excess heat in urban areas. Finally, the survey findings on the human-place relationship in urban environments of Melbourne’s Central Business District (CBD) under various meteorological conditions at the local level was presented. The findings will significantly contribute to enhancing the resilience and adaptation strategies for urban heat.