Sustainable rainwater management may counteract the effects of climate change and significantly improve the distorted water balance in urbanized catchments. However, despite the hydrologic advantages of rainwater management, acceptance and willingness-to-pay in the local society are required. This paper presents an assessment of the financial aspects, i.e., the cost-efficiency and economic feasibility, of various designs of rainwater management for a small-scale urban housing community in Lublin, Poland. The research was performed for a housing community covering approx. 1.38 ha and five multi-family residential buildings. The proposed designs covered rainwater harvesting systems, supported with extensive green roofs, with rainwater retained in underground or above-ground reservoirs, used with variable demand for watering the green areas and for underground parking lot flushing. For each designed variant, the investment as well as operation and maintenance costs were estimated. The assessment of the cost-efficiency and profitability of the proposed rainwater management systems was based on three indicators: Dynamic Generation Costs, Payback Period and Benefits–Costs Ratio. The performed calculations showed that only two designs, utilizing above-ground rainwater reservoirs, could be assessed as economically profitable. Thus, local communities may be unable to financially sustain investments in sustainable rainwater management, so it seems that financial support is required.