The last treatment of Gonolobinae (Apocynaceae, Asclepiadoideae) in the West Indies is over a hundred years old and a number of new species have been described since. Although Fischeria and Gonolobus s. s. were revised recently, a complementary, comprehensive, recent regional treatment of Matelea s. l. is lacking. Considering the rarity of taxa of Matelea s. l. in the West Indies, thirty-three of thirty-six taxa are endemic to a single island each, and that nearly half of the known species have been described since Schlechter's treatment of 1899, the objective of the present study is to provide a synopsis of the genus in the area to facilitate field recognition and future collections. The treatment is based on critical study of ca. 250 specimens of the fifty-some known species in Caribbean Gonolobinae, fieldwork in the region, and molecular analyses. In addition to a comprehensive key and descriptions, illustrations of the complex gynostegial coronas are provided here for the first time for numerous taxa. A new combination is made in Matelea for Gonolobus haitiensis: Matelea haitiensis.