Paleoclimate research in the Maya region of Mesoamerica provides compelling evidence of drought during key periods of cultural transition in Maya society. These include the transition from the Preclassic to the Classic, and from Classic to the Postclassic. Previous research emphasized a causal relationship between drought and cultural change, or so-called “collapse” in the Maya region. Recent advances in the range and precision of climate-sensitive proxies and the development of new archives have enabled quantitative reconstructions of past hydroclimate, as well as providing evidence of high impact, short-duration events, such as tropical cyclones. Simultaneously, archaeological research has unearthed widespread evidence of technologies used by the Maya to exert control over water resources in urban, rural, and agricultural settings. Evidence suggests that many of these water features were in use for multiple generations, possibly centuries, and many were constructed during the Terminal Preclassic and Terminal Classic periods. We suggest that, given the availability of new archaeological and paleoclimate records, these data can be combined to identify the full complexity of Maya adaptation to hydroclimate variability to emphasize adaptation and resilience to both water scarcity and over-abundance (e.g., flooding). Such syntheses, which can offer lessons for present-day efforts to grapple with regional climate change, will benefit from additional studies in data-poor zones of the Maya region, as well as public archiving of paleoclimate and archaeological data.