In this study, acid dyeable poly(lactic acid) (PLA) fiber was produced with the addition of octaammonium polyhedral oligomeric silsesquioxane (OA-POSS) nanoparticle during the melt spinning. The tensile, thermal and morphological properties of the fiber samples were characterized by tensile testing, differential scanning calorimetry, scanning electron microscopy and transmission electron microscopy. Two different anionic dyes, a disulphonated 1:2 premetallised acid dye and monosulphonated non-metallised, were used. The effects of dyeing conditions including dyeing temperature and time, OA-POSS concentration, anionic dye types and concentrations were investigated on the dyeability properties of the PLA fiber samples. It was concluded that the percent crystallinity and the tensile strength of pure PLA fiber decreased as the added amount of OA-POSS increased. According to the dyeing results, the addition of OA-POSS greatly improved the dyeability of the PLA fiber with anionic dyes by introducing ion-ion interaction between the terminal ammonium groups of POSS nanoparticle and the sulphonyl groups of dye molecules.