The reproductive phenology of plants has profound influence on ecosystem dynamics including plant–animal interactions. Broad phenological patterns, especially the timing of reproduction, may result from long‐term climate trends and co‐evolution between plants and their pollinators, dispersers, and predators. Yet, interannual climate variation and local abiotic conditions may also affect the timing and magnitude of plant reproduction. Understanding the patterns of and controls on plant reproduction are crucial for conservation efforts under a changing global climate and rapidly expanding human development. However, phenology studies from the Neotropics are sparse. Here, we examine the relative timing and magnitude of fleshy‐fruited plant reproduction during the winter dry season in subtropical dry forest on Eleuthera, The Bahamas over a nine‐year period. At least 47 species were observed with some dry season reproductive activity, but only 17% showed evidence of a fruiting peak or continuous reproduction. Overall fruit abundance generally declined through the dry season, but flower production increased between mid and late dry season. Variation in fruit and flower abundance among years was related to temperature and rainfall, but local site conditions—particularly successional stage and groundwater availability—explained more variability in reproductive activity than climate variation. Groundwater availability had a particularly strong positive influence on flower and fruit abundance at the end of the dry season, a critical time for migrant frugivores preparing to return to their breeding grounds. This emphasizes the importance of protecting sites with accessible groundwater to conserve biodiversity in the archipelago and elsewhere.