Changing our unsustainable linear water management pattern is necessary to face growing global water challenges. This article proposes an integrated framework to analyse and understand the role of different contextual conditions in the possible transition towards water circularity. Our framework combines a systematic multi-level perspective to explore the water system and the institutional work theory for technology legitimation. The framework consists of the following stages: (1) describing and understanding the water context, (2) assessment of the selected technologies’ circularity level, (3) assessment of the alternative circular technologies’ legitimacy, and (4) identification of the legitimation actions to support the upscale of alternative circular technologies. The practical applicability of the integrated assessment framework and its four assessment stages was demonstrated in the exploration of circular water technologies for the horticulture sector in Westland, the Netherlands. The results revealed the conditions that hinder or enable the legitimation of the circular water technologies, such as political environmentalism, trust in water governing authorities, and technical, financial, and knowledge capabilities.