Since complex urban systems are a combination of different spatial typologies and may have various complex characteristics (human, environmental, social, economic, political, and cultural), decision-making cannot be done without a holistic approach and complex analysis and evaluation of the possible development scenarios. This is especially true in today’s world, where spatial and urban planning must consider various objectives such as sustainable development, accessibility, landscape characteristics, and public interests on a strategic level. This results in the need to use appropriate decision support and decision-making tools in the strategic urban planning process of complex urban environments with Historic Urban Landscapes (HUL) characteristics to improve urban development and resilience. The proposed evaluation model, “Strategic Planning for Urban Resilience—SPUR model,” is based on a holistic approach to spatial planning with an emphasis on the strategic sustainable development of urban voids as HULs and was tested on the case study of the Delta area in the City of Rijeka, Croatia. The proposed holistic approach can help in scenario building, evaluation, and selection of planning alternatives, as well as decision-making processes in urban management, by enabling the evaluation and control of complex scenarios from a sustainable development perspective.