We describe females and males of Osmia (Melanosmia) calaminthae sp. n., an apparent floral specialist on Calamintha ashei ( Lamiaceae), and provide observations on the behavior of female bees on flowers of this plant. We also provide diagnostic information for Osmia (Diceratosmia) conjunctoides Robertson, stat. n., and synonymize Osmia (Diceratosmia) subfasciata miamiensis Mitchell with Osmia conjunctoides syn. n. Females of both Osmia calaminthae and Osmia conjunctoides are unique among North American Osmia for having short, erect, simple facial hairs, which are apparent adaptations for collecting pollen from nototribic flowers. Osmia calaminthae is currently only known from sandy scrub at four nearby sites in the southern Lake Wales Ridge in Highlands County, Florida, USA, while Osmia conjunctoides is known from limited but widespread sites in the southeastern USA. We discuss the conservation status of both species based on known or speculated floral associates and distributions.