The article deals with the structural and semantic types of comparisons in the short stories of Italian cycle written by Kotsiubynskyi. It is found the semantic nature of figurative comparisons in the texts of the writer; determined and defined the varieties of associative meaning transfer; delimited the grammatical types of comparisons. For the beauty connoisseur and esthete – M. Kotsiubynskyi exotic nature of the Mediterranean land presented new space and vivid images, which are reproduced in the works of the author with original artistic means. One of them is a figurative comparison that are mainly individual authors. So, in this paper we have a goal to point out and characterize structural and semantic types of comparisons in the short stories of Mediterranean cycle by Kotsiubynskyi. In modern linguistic science the comparisons are shared in structure, with both the semantic and formal criteria. According to the semantics all comparisons are defined as three-members structure: subject of comparisons, object of comparison and feature of comparison: color, size, shape, smell, feeling, quality, property and so on. Among the figurative comparisons in the short stories by Kotsiubynskyi individual authors ones dominate, especially anthropomorphic, zoomorphic, biomorphic, natural, mythical variants. These comparisons are based on complex intellectual and aesthetic associations that allow the author to create exquisite landscapes marked traits of Impressionism. As for the grammar aspect comparative structures are the common and uncommon ones with conjunctions, common and uncommon apposition, a relative clause of the compound sentence.