The vulnerability of urban areas to flooding increased along with the rapid urbanization process. The study selected the Subosukawonosraten (Surakarta, Boyolali, Sukoharjo, Karanganyar, Wonogiri, Sragen, and Klaten) Region as a case study to assess the vulnerability. The ESA framework: exposure, sensitivity, and adaptability—is applied. Exposure is examined using the built-up index in 2020. Sensitivity is assessed based on population density in 2020. Additionally, precipitation and topography are also discussed. The study uses hot spot analysis to pinpoint the most populated and developed areas of the region, which are Surakarta and its peri-urban. Following that, the study investigates to what extent urban villages situated in this hot spot can adapt in light of the floods that often occur in the region. The findings imply that, primarily because of rapid urbanization, the strategy to deal with vulnerability should be considered an important regional-scale strategy that should integrate technical and community-based development approaches to establish a more sustainable strategy for resiliency.