Two new species of Pleurothallis are described from the Cordillera de Guanacaste in northern Costa Rica. Both novelties belong to Pleurothallis sect. Macrophyllae-Fasciculatae, among which they can be recognised by their fasciculate inflorescence with numerous simultaneously produced flowers, a rare feature in the species-rich group. This feature is shared with Pleurothallis bothros, putatively their closest relative. Both novelties may be distinguished from that species by their non-spreading (vs. spreading), pale yellow to pinkish flowers (vs. green) and broad, oblique petals (vs. narrow, straight). Pleurothallis hawkingii can be easily distinguished from Pleurothallis vide-vallis by its broader panduriform lip with raised margins and depressed basal glenion (vs. narrow lanceolate lip, lacking raised margins, with the glenion raised on a high basal callus).