The flora and vegetation of oceanic islands have been deeply affected by human settlement and further landscape modifications during prehistoric and historical times. The study of these transformations is of interest not only for understanding how current island biotas and ecological communities have been shaped but also for informing biodiversity and ecosystem conservation. This paper compares two oceanic insular entities of disparate geographical, environmental, biological, historical and cultural characteristics—Rapa Nui (Pacific Ocean) and the Azores Islands (Atlantic Ocean)—in terms of human settlement and further landscape anthropization. The similarities and differences between these islands/archipelagos are discussed considering their permanent colonization, the possibility of earlier settlements, the removal of the original forests and the further landscape transformations leading to either full floristic/vegetational degradation (Rapa Nui) or major replacement (Azores). This comparison uses evidence from varied disciplines, notably paleoecology, archaeology, anthropology and history, to obtain a holistic view of the development of the respective socioecological systems from a human ecodynamic perspective. The most relevant issues still to be resolved are identified and some prospects for future research are suggested. The cases of Rapa Nui and Azores Islands may help set a conceptual basis for ocean-wide global comparisons among oceanic islands/archipelagos.