The Algarve region, located in the south of Portugal, is a well-known tourism destination that seeks to be sustainable and competitive. The local administration looks to establish a collaborative network, where stakeholders take a crucial role. The research aims to appeal to the accommodations and food services stakeholders to have a shared vision of the issues and priorities related to sustainable tourism development. Their perception is a critical factor in making decisions regarding the region’s competitiveness. Algarve’s two major and leading associations of the tourism supply sector AIHSA and AHETA were invited to participate in the study. Based on the responses of an online questionnaire, an artificial intelligence algorithm was applied to the data to identify the common and divergent aspects. The conceptual model developed is based on a simplified model of psychological ownership. The results highlight a convergent perspective regarding sustainability challenges, namely, natural resources and biodiversity, safety, and supply chain. However, hotels and restaurants do not reflect the same perception regarding sustainability initiatives, e-tourism, or free internet access. These divergences are essential results since they indicated which issues require local authorities’ priority intervention.