The expansion of construction zones, transportation, and utilities for industry and high-tech areas due to human activities has caused the deterioration of the natural ecological environment. As cities face problems related to the surface urban heat island (SUHI) effect and environmental pollution, there is an urgent need to develop new methods for the ecological–microclimatic assessment and structural–functional planning of urban areas. The main goal of this study was to demonstrate the evolution of the surface urban heat island (SUHI) effect in Moscow over a long period and to determine the interaction between SUHIs and urban pollution islands (UPIs) using a geospatial analysis platform while optimizing vegetation classification with machine learning. Additionally, we are creating a digital database for modeling the sustainability of cities on the GEE platform using cloud computing. This study used cloud computing and remote sensing image analysis platforms for a 17-year temporal-series ecological–microclimatic assessment, which provided a sequence of values describing the ongoing process of changes in the ecological conditions of Moscow over time. Combining machine learning with the random forest algorithm (RF) improved vegetation classification accuracy while reducing computation time. The study findings demonstrated how the SUHI affected Moscow’s territory and showed the urban areas significantly impacted by this phenomenon. The locations of surface urban heat islands in Moscow and areas affected by SUHI and UPI were identified using numerical modeling of the urban thermal field variance index (UTFVI). From the findings, we identified the need to develop a new method for obtaining geospatial data for assessing the interaction between UPIs and SUHIs using cloud computing and mathematical data models.