This article uses sustainability as a lens through which to examine affordable housing policies in geographically-isolated island communities, with the intent of assessing the utility of using sustainable development as a guide to policy decision-making. Focusing on the case of Key West, Florida, the article points to the conflicts that must be reconciled to achieve true sustainability. The study applies criteria to identify policy solutions for the provision and retention of affordable housing in island communities, and at the same time provides an application of the sustainable development concept as a policy guide. [Author Abstract]