We report on the recording and analysis of 17 petroglyph or pictograph sites, containing a total of 168 glyphic units, carried out as part of a large scale survey of the ancient district (moku) of Kahikinui, on south-eastern Maui Island, Hawaiian Islands. In contrast with previous studies which have tended to view Hawaiian petroglyphs as divorced from their larger archaeological context, we analyse and interpret this corpus in terms of a landscape-level settlement analysis. The Kahikinui petroglyphs exhibit a regular and limited range of motifs, with certain styles of anthropomorphs and zoomorphs (especially dogs) dominating; petroglyphs dating to the early post-European contact period are characterised by Roman lettering reflecting early missionary efforts at literacy. Petroglyphs are strongly associated either with an early historic-period trail, or with rockshelters and cliff faces where there is evidence for freshwater springs or seeps. In the arid environment of Kahikinui, freshwater was a precious resource, and the petroglyphs may have served as territorial markers, or signs of individual ownership or rights of access. Excavations at three rockshelter sites with petroglyphs provide indirect evidence for dating these petroglyphs to the late prehistoric era (16th to 18th centuries AD). Comparisons with petroglyph sites on other islands in the Hawaiian archipelago indicate the existence of distinct regional variations.