Urbanized delta areas worldwide share a growing tendency of exposure to water stress induced by the effects of climate change and anthropogenic factors, threatening the operation of infrastructure systems and future urban development. The important synergistic impacts coexisting with freshwater scarcity are increasing urbanization rates, subsiding soils, saltwater intrusion in aquifers and rivers, coastal erosion, and increased flooding. Innovative design strategies and concepts for the integration of decentralized rainwater management measures can contribute to the integrated and climate resilient planning of urban spaces that are threatened by climate change scenarios that worsen the security of urban infrastructures and the future availability of fresh water. Decentralized rainwater management, including retention, storage, and reuse strategies that are integrated into spatial planning and urban design, can reduce flood risks while simultaneously enhancing freshwater availability. This paper discusses a paradigm shift in urban water management, from centralized to decentralized management (that is, from threats to opportunities), using the example of two case studies. Concepts and strategies for building climate resilient cities, which address flood control, the protection of freshwater resources, and the harmonization of a natural and more sustainable water balance, are presented for Almere (Rhine Schelde Delta, The Netherlands) and Hsingchu (Dotzpu Delta, Taiwan).