To dye poly(lactic acid) (PLA) fiber with natural dyes has gained importance in recent years due to the production of the fully eco-friendly textile products. In this study, pure and modified PLA fibers with two different POSS nanoparticles, namely N-phenyl aminopropyl POSS (AP-POSS) and octa (aminophenyl) polyhedral oligomeric silsesquioxane (OAPPOSS), are dyed with three different natural dyes including alizarin, lawsone and indigo. The effects of the dyeing conditions including dyeing temperature and time, POSS nanoparticle concentration, natural dye types and concentrations are investigated on the dyeability properties of the PLA fiber samples. The wash and light fastness of the fiber samples are also investigated. According to the dyeability results, it is concluded that POSS nanoparticles are effective for increasing the dyeability of the PLA fiber with all natural dyes used in this study. As the added amount of the POSS nanoparticle increases, the dyeability of the PLA fiber increases. When the performances of the POSS nanoparticles are compared, it is seen that OAP-POSS is more effective than the AP-POSS nanoparticle.