The Konavle region was part of the territory of the Republic of Dubrovnik (Ragusa) from 1419/1426 until the fall of the Republic in 1808. Due to individual appointments for different public services, citizens of Dubrovnik often became residents of Konavle, and later on even landowners after the stategoverned distribution of land. Architectural structures erected on these estates were primarily agricultural buildings, but also included residential structures with leisure areas (terraces, belvederes, pathways, ponds) and chapels. These structures provided a basis for the development of villas in the Konavle region (destined for both residential and agricultural use), most of which are nowadays poorly documented and mostly unprotected elements of cultural heritage, despite their significant potential for scholarly research. Through the analysis of avaliable literature and direct field work, this thesis discusses aspects of villeggiatura in Konavle and provides historical information, descriptions and photographic documentation of 24 villas spread throughout the area. In January 2019, the Croatian Ministry of Science and Education issued an Act on the national curriculum for the Visual Arts subject in elementary and high schools (Odluka o donošenju kurikuluma za nastavni predmet Likovne kulture za osnovne škole i Likovne umjetnosti za gimnazije u Republici Hrvatskoj). This thesis also discusses possible methods of implementing the topic of villas and villeggiatura in Konavle during the Republic of Dubrovnik as part of the Visual Arts subject and in accordance with the aforementioned Act. Key words: Konavle, Republic of Dubrovnik, villas, villeggiatura, Visual Art