Halophytic communities such as mangrove forests and buttonwood hammocks tend to border freshwater plant communities as sharp ecotones. Most studies attribute this purely to underlying physical templates, such as groundwater salinity gradients caused by tidal flux and topography. However, a few recent studies hypothesize that self-reinforcing feedback between vegetation and vadose zone salinity are also involved and create a bistable situation in which either halophytic dominated habitat or freshwater plant communities may dominate as alternative stable states. Here, we revisit the bistability hypothesis and demonstrate the mechanisms that result in bistability. We demonstrate with remote sensing imagery the sharp boundaries between freshwater hardwood hammock communities in southern Florida and halophytic communities such as buttonwood hammocks and mangroves. We further document from the literature how transpiration of mangroves and freshwater plants respond differently to vadose zone salinity, thus altering the salinity through feedback. Using mathematical models, we show how the self-reinforcing feedback, together with physical template, controls the ecotones between halophytic and freshwater communities. Regions of bistability along environmental gradients of salinity have the potential for large-scale vegetation shifts following pulse disturbances such as hurricane tidal surges in Florida, or tsunamis in other regions. The size of the region of bistability can be large for low-lying coastal habitat due to the saline water table, which extends inland due to salinity intrusion. We suggest coupling ecological and hydrologic processes as a framework for future studies.