Medicine and architecture are disciplines with the main objectives of satisfying the fundamental needs of human beings: health, comfort, well-being, safety, and ensuring an acceptable quality of life in a sustainable habitat. In both areas of knowledge, the advances and the most innovative proposals in the fields of research and teaching are focused on transversal knowledge and the use of learning methods through problem solving (learning by doing). The student competitions called “Solar Decathlon” are focused on the development of these concepts, in which prototypes of sustainable and, as far as possible, healthy social housing are tested. In these university competitions, the design of energy-efficient and comfortable living environments that contribute to the health of the occupants are encouraged; however, the methodology for evaluating the “comfort conditions” stipulated in the competition rules considers only parameters that can be monitored by sensors. For this article, the prototypes presented by the “Solar Decathlon Team of the University of Seville” to the editions of said competition held in Latin America and Europe (in 2015 and 2019, respectively) are being studied. The present research starts from the fact that the unique consideration of measurable indices (such as temperature, humidity, etc.), is clearly insufficient when it comes to evaluating the real conditions of habitability and comfort that a domestic architectural space presents. For this reason, a theoretical–practical analysis is carried out by means of surveys, with the final objective of determining a methodology for evaluating comfort—complementary to that of the competition—which assesses other relevant issues and which, in short, takes into account the repercussion on people’s health. From our analysis, we conclude that at least these two methodologies should be used to evaluate comfort because they are individually considered incomplete in terms of the data provided by each one of them. The survey-based methodology provides complementary information on comfort and health that could be taken into account in future editions of Solar Decathlon.