Urban heat islands (UHIs) are a significant environmental problem, exacerbating the urban climate and affecting human health in the Asir region of Saudi Arabia. The need to understand the spatio-temporal dynamics of UHI in the context of urban expansion is crucial for sustainable urban planning. The aim of this study was to quantify the changes in land use and land cover (LULC) and urbanization, assess the expansion process of UHI, and analyze its connectivity in order to develop strategies to mitigate UHI in an urban context over a 30-year period from 1990 to 2020. Using remote sensing data, LULC changes were analyzed with a random forest model. LULC change rate (LCCR), land cover intensity (LCI), and landscape expansion index (LEI) were calculated to quantify urbanization. The land surface temperature for the study period was calculated using the mono-window algorithm. The UHI effect was analyzed using an integrated radius and non-linear regression approach, fitting SUHI data to polynomial curves and identifying turning points based on the regression derivative for UHI intensity belts to quantify the expansion and intensification of UHI. Landscape metrics such as the aggregation index (AI), landscape shape index (LSI), and four other matrices were calculated to assess UHI morphology and connectivity of the UHI. In addition, the LEI was adopted to measure the extent of UHI growth patterns. From 1990 to 2020, the study area experienced significant urbanization, with the built-up area increasing from 69.40 to 338.74 km2, an increase of 1.923 to 9.385% of the total area. This expansion included growth in peripheral areas of 129.33 km2, peripheral expansion of 85.40 km2, and infilling of 3.80 km2. At the same time, the UHI effect intensified with an increase in mean LST from 40.55 to 46.73°C. The spatial extent of the UHI increased, as shown by the increase in areas with an LST above 50°C from 36.58 km2 in 1990 to 133.52 km2 in 2020. The connectivity of the UHI also increased, as shown by the increase in the AI from 38.91 to 41.30 and the LSI from 56.72 to 93.64, reflecting a more irregular and fragmented urban landscape. In parallel to these urban changes, the area classified as UHI increased significantly, with the peripheral areas expanding from 23.99 km2 in the period 1990-2000 to 80.86 km2 in the period 2000-2020. Peripheral areas also grew significantly from 36.42 to 96.27 km2, contributing to an overall more pronounced and interconnected UHI effect by 2020. This study provides a comprehensive analysis of urban expansion and its thermal impacts. It highlights the need for integrated urban planning that includes strategies to mitigate the UHI effect, such as improving green infrastructure, optimizing land use, and improving urban design to counteract the negative effects of urbanization.