An earpiece in accordance with at least some embodiments of the present technology includes a housing and a speaker within the housing. The earpiece also includes an antenna at least partially embedded within a wall of the housing. The wall includes a window portion and an opaque portion extending around the window portion. The antenna is visible from outside the housing via the window portion. The window portion includes a transparent filler within an elongate groove in the wall. The antenna includes a radiating element within the groove, and feeding and shorting pins extending through respective openings between the groove to an interior of the housing. Making the earpiece can include disposing filler material over the radiating element, increasing a hardness of the filler material, and abrading an outer surface of the wall at the filler material to form a smooth surface.