This article presents the results of the population studies of rare protected species Orchis punctulata (Orchidaceae). Based on analysis of local floras in eastern and southeastern Crimea and personal observations, we identified the three most numerous populations of O. punctulata: two in the steppe (on the Tepe-Oba mountain ridge) and one in forest communities (on the Kiziltash mountain ridge). The ontogenetic, demographic, and vitality structures of the populations were studied. We also assessed the life strategies of the species in different habitats. The populations in steppe communities were characterized by high number and density parameters. O. punctulate often formed large clusters and was dominated here. A small number and low density characterized the population in the forest community; the distribution of individuals within the population was scattered. The age spectra were also different. The populations in steppe communities had a left-sided spectrum with a maximum in immature individuals, while in forest communities, it had a bimodal spectrum with maximums in generative (with a predominance of mature and old generative) and immature individuals. Specimens from forest communities were more extensive than those of steppe communities, they had longer leaves and inflorescences, and their inflorescences had a more significant number of flowers. As a result, the population in the forest community had a higher vitality index. It included individuals of the highest and middle class of vitality. The populations in the steppe community consisted of all classes of vitality or only of middle and lower classes. Thus, optimal environmental conditions for the growth of species are in forests. At the same time, a low level of regeneration and competition from other plants hinder its wide distribution. As a result, the species exserts as a phytocenotic patient (S-strategy). In steppe communities, the species is characterized by a mixed patient-explerant-violant strategy (SRC strategy).