Two new species of the families Agelenidae (Coelotinae) and Amaurobiidae are described from Okinawa Island, southwestern Japan, under the names Coelotes kunigamiensis sp. n. and Callobius breviprocessus sp. n. Coelotes kunigamiensis resembles C. motobuensis Shimojana, 2000 but is characterized by the male palp having a greatly bent conductor, thin epigynal teeth situated distant from each other, and blackish markings derived from the internal genitalia situated in the central portion of the epigyne. Callobius breviprocessus is related to C. amamiensisOkumura, Honki & Ohba, 2018 and C. yakushimensisOkumura, 2010, but is characterized by having a short mesal process and a broad dorsal process on the tibia of male palp, the semicircular lateral lobes of the epigyne, and the median lobe almost circular. The male palpal tibiae and female genital organs of these three species of Callobius are shown (with a correction of the former figures given in Okumura, Honki & Ohba (2018), and their morphological difference is discussed.