The presence of vertical cross-formational fluid migration passageways within sedimentary basins can profoundly impact aquifer and reservoir fluid-flow and their identification is fundamental to informing management of subsurface fluid resources (groundwater, oil, gas). In an onshore and offshore southeastern part of Florida, 2D/3D seismic-reflection and bathymetry data document ~153 vertical columnar structures composed of reflection disruptions up to 760 m in the height and averaging 360 m in diameter, and ~ 219 subcircular to circular seafloor depressions up to 1010 m wide. Our study focuses on these features found within the offshore shallow-marine carbonate Miami Terrace platform, which drowned approximately at the end of the middle Miocene, and within overlying Plio-Quaternary deep-water carbonate slope and drift deposits. Most columnar structures are rooted in stratiform aquifers of the Miami Terrace platform and associated with faults or fault intersections produced by Eocene and circa late Miocene tectonics. The columns commonly terminate within the platform or as subcircular depressions along an amalgamated karstic and drowning unconformity at the platform top. The columns typically stretch upwards from a zone of deep karst cavity collapse through the Miami Terrace platform with upward decreasing sag on internal reflections. Following drowning and Plio-Quaternary partial burial of the Miami Terrace platform by deep-water deposits, the subcircular depressions and faults along the platform top were points of origin for a second phase of column growth upward into the deep-water deposits. The continuation of deep platform cavity collapse and column evolution produced pockmarks along paleo-seafloors within the deep-water deposits and at the present-day sea floor. The Plio-Quaternary pockmarks formed at water depths too deep to suggest an origin related to meteoric karst above or near sea level, but rather their formation is suggested to be related to cyclic sea level falls that drove increased groundwater head and density gradients, and seafloor discharge of offshore freshened groundwater sourced from the underlying platform. Mixing of freshened groundwater and seawater at the seafloor discharge sites plausibly drove dissolution of the host deep-water deposits that contributed to the formation of the pockmarks and erosion by groundwater venting and current scouring.Seaward of the Plio-Quaternary seafloor pockmarks, at the late-middle Miocene upper slope of the Miami Terrace platform and along the regional karst/drowning unconformity is a slope-parallel band of ~188 densely distributed subcircular seafloor depressions with diameters up to 1010 m at water depths up to 663 m. It is plausible that along the upper slope, faults and fractures produced by gravity-driven slope instability and possibly tectonics formed a dense network of fluid passageways that promoted upward artesian freshened groundwater flow to sites of discharge where mixing with seawater generated limestone dissolution and the depressions. But tectonic uplift may have forced emersion and initial meteoric sinkhole formation circa late Miocene with later enhancement by freshened groundwater discharge and bottom current erosion.