Urbanization reflects the overall behavior of human society; thus, characterization of its associated spatial and temporal trends has been extensively researched. This study examines the process of urban expansion in the Huaihe River Basin (HRB) which is a key transition region within China’s urban system. In order to grasp the urban expansion process in different temporal sequences objectively, rapidly, and accurately, we used remote sensing data to assess the urban expansion in time and space. Urban expansion rules were defined for the urban area, urbanization intensification, extended dynamic degree, and spatial pattern. The research findings show that the urban area expansion speed was at medium level throughout the entire HRB and within each province. Presently, the formation of a whole urban agglomeration or urban system is not complete in the HRB; urban expansion in the HRB displayed space-time disequilibrium tendencies during 1998–2013