In the last three years there has been a proliferation of regional building rating systems across the Middle East. Most those emerging rating systems and labels imitate the British and American rating systems BREEAM and LEED that emerge from an impact reduction paradigm. Thus they are neglecting the local historic, climatic, economic, technological, cultural and social context. This paper presents two case studies of a recently constructed ecolodges in Siwa, Egypt, that performs beyond the existing rating systems requirements. The paper illustrates the environmental and sustainability design strategies adapted to El-Babinshal and Adrère Amellal buildings’ context. In this study, various design strategies are surveyed and their response to climate, occupants and society is evaluated. The paper presents a set of sustainability principles addressing (1) the site, (2) water, (3) energy, (4) resources, (5) comfort, (6) heritage and (7) social responsibility. In addition, the building is examined across the environmental criteria of LEED, Estidama and the Egyptian Green Pyramid Rating System. Results showed that the building failed to comply with the three rating systems despite winning the Egyptian Hassan Fathy Award for environmental design. The paper elaborates on this conflict and presents recommendations to improve the questioned rating systems and support architects with the principles and strategies for sustainable design.