Tree islands are centers of biodiversity within the Florida Everglades, USA, but the factors controlling their distribution, formation, and development are poorly understood. We use pollen assemblages from tree islands throughout the greater Everglades ecosystem to reconstruct the timing of tree island formation, patterns of development, and response to specific climatic and environmental stressors. These data indicate that fixed (teardrop-shaped) and strand tree islands developed well before substantial human alteration of the system, with initial tree island vegetation in place between 3500 and 500 calibrated years before present (cal yr BP), depending on the location in the Everglades wetland. Tree island development appears to have been triggered by regional- to global-scale climatic events at 2800 cal yr BP, 1600–1500 cal yr BP, 1200–1000 cal yr BP (early Medieval Warm Period), and 500–200 cal yr BP (Little Ice Age). These periods correspond to drought intervals documented in Central and South America and periods of southward displacement of the Intertropical Convergence Zone. The records indicate a coherence of climate patterns in both subtropical North America and the Northern Hemisphere Neotropics. Water management practices of the 20th century altered plant communities and size of tree islands throughout the Everglades. Responses range from loss of tree islands due to artificially long hydroperiods and deep water to expansion of tree islands after flow reductions. These data provide evidence for the rapidity of tree island response to specific hydrologic change and facilitate prediction of the response to future changes associated with Everglades restoration plans.