Oasis settlements in Saharan lands present a particular model of life for rural individuals’ adaptation to environmental challenges. This study investigated human outdoor thermal comfort in a palm grove of the Tolga region, Algeria, during the phenological cycle of the date palm. Date palms are the primary economic source of the cultivators, who mainly live in houses inside the cultivated area. For this study, an area of 21 hectares with 220 palm trees was selected. The phenological cycle of the date palm was divided into three growth stages, including seasonal variations as well. The cycle covers a period of 8 months from March to November. Therefore, on-site monitoring of the microclimate was performed during March–November 2021. The climatic factors of air temperature and humidity were monitored at an interval of 10 min. The discomfort index based on temperature ranges covering discomfort conditions was used. The results showed that the cultivators work under extreme temperatures for 5.5 months during the phenological cycle. The spring period was more comfortable, while slight to extreme discomfort was observed in the summer and fall seasons, especially between midday and 7 p.m. Temperatures below 25 °C are comfortable for the cultivators; however, severe discomfort occurs at 30 °C or above. Moreover, the humidity was not a dominant factor for discomfort. These findings can be helpful for architects and planners to devise solutions that can fulfil human comfort requirements and date palm cultivar conditions, specifically during extreme thermal situations.