Saudi Arabia witnessed unprecedented urban development starting from the 1930s due to oil discovery, leading to the construction of new contemporary cities and high-tech buildings. Recently, starting from the late 1990s, an increasing feeling of esteem toward vernacular architecture and local traditions has promoted several heritage rehabilitation projects. This paper aims to assess selected urban heritage interventions to highlight the importance of sustainable approaches in heritage reuse. An assessment of sustainable reuse was conducted by adopting sustainability criteria and principles in compliance with Saudi Arabia’s national vision for 2030 (Saudi Vision 2030), which targets sustainable growth in the post-oil era. Analyses and data collection make it possible to compare four selected case studies based on materials and techniques for preservation, governmental institutions involved, the assessed methodologies of intervention, and relevant parameters (legibility, reversibility, overshadowing, alteration, replacement, and anastylosis). Results show how different institutions have adopted diverse approaches in conservative methodologies based on heritage values to provide flexibility in the reuse of buildings and adaptation to contemporary needs. Assessing the sustainable reuses of Saudi heritage can lead to a strategic change in national growth targeting social, economic, environmental, and ecologic results.