Nature-based solutions (NbS) are increasingly recognized as viable tools for sustainable urban water management. This article explores the implementation of NbS in two distinct cities, Singapore and Lisbon, to demonstrate that NbS can work in very different contexts and spark new thoughts on the urban–nature relationship and to identify commonalities that drive and enable the implementation of NbS in different context. Literature review-based research was conducted to examine the types of NbS implemented, the common drivers, the governance model, and the plural functionalities of the solutions. The research shows that, despite the differences, the two cities shared common drivers (including water supply, flood control, and resident demand for green space) and goals, such as improving water quality and overall quality of life, through the deployment of NbS. With rapid urban expansion, water use increase, and the impacts of climate change, NbS can be effective tools to deliver integrated benefits and improve the liveability of cities.