Due to the negative consequences of urban heat islands (UHI) on urban ecology, Identifying the regional variation of land surface temperature (LST) offers a clear picture of the UHI phenomena and will aid in the introduction of appropriate mitigation techniques to address the UHI's advancing impact. Delineating the impact of UHI on land cover changes and land surface temperature (LST) is of uttermost importance due to its dynamic nature. This study makes use of Landsat Images TM, ETM and OLI sensors over the southwestern region of Nigeria, consisting of Ekiti, Osun, Ondo, Oyo, Ogun and Lagos. A supervised classification was performed by creating a training sample from four classifications consisting of vegetation, built-up, water body, and bare surface. Our results during the observed period (1986, 2002, and 2007) shows that the distribution pattern has changed as a result of changing urban surface characteristics and the influence of anthropogenic activities. The result of the research revealed that Southwest Nigeria has gone through rapid urban expansion that is expected to continue in the future, 20% decline in vegetal coverage 15% increase in bare soil amounting to a total of 35% change caused by human activities during the investigation period. The result further reveals the existence of an inverse connection between LST and NDVI with correlation coefficients of −0.8738, −0.8594, and −0.8546 respectively, which suggests that the growth of vegetation in any geographical location reduces the intensity of the land surface temperature over the area, which might be used to minimize the impacts of Urban Heat Island. In addition, thermal and evapotranspiration capacity of water also contributed to the comparatively high temperature. Hence, to achieve the sustainable environment in this region, urban planning strategies that include embracing green initiatives such as planting of trees to improve urban forestry should be adopted.