The expansion of cities entails the abandonment of forest and agricultural lands, and these lands’ conversion into urban areas, which results in substantial impacts on ecosystems. Monitoring these changes and planning urban development can be successfully achieved using multitemporal remotely sensed data, spatial metrics, and modeling. In this paper, urban land use change analysis and modeling was carried out for the Concelhos of Setúbal and Sesimbra in Portugal. An existing land cover map for the year 1990, together with two derived land cover maps from multispectral satellite images for the years 2000 and 2006, were utilized using an object-oriented classification approach. Classification accuracy assessment revealed satisfactory results that fulfilled minimum standard accuracy levels. Urban land use dynamics, in terms of both patterns and quantities, were studied using selected landscape metrics and the Shannon Entropy index. Results show that urban areas increased by 91.11% between 1990 and 2006. In contrast, the change was only 6.34% between 2000 and 2006. The entropy value was 0.73 for both municipalities in 1990, indicating a high rate of urban sprawl in the area. In 2006, this value, for both Sesimbra and Setúbal, reached almost 0.90. This is demonstrative of a tendency toward intensive urban sprawl. Urban land use change for the year 2020 was modeled using a Cellular Automata based approach. The predictive power of the model was successfully validated using Kappa variations. Projected land cover changes show a growing tendency in urban land use, which might threaten areas that are currently reserved for natural parks and agricultural lands.