The 2017 Atlantic hurricane season was the most active since 2005 and was classified as an extremely active year of coastal storms. Hurricane Irma caused significant damage in the Caribbean islands and Florida Keys. After the storm, the authors developed standardized metrics with which to assess physical damage to natural and artificial shorelines and near-coast residential structures. These metrics were used to collect damage data for 332 shorelines and 262 structures in Key West and Big Pine Key, Florida, during a reconnaissance field study in mid-October 2017. Based on peak environmental conditions extracted from a numerical hindcast of the storm, relationships among hazard intensity, structural damage, and dominant shoreline archetype were investigated. Results indicated that structures located in areas subject to wind speeds greater than experienced more severe damage than structures located in areas with lower wind speeds. Mangrove shorelines were identified as resilient to environmental conditions during Hurricane Irma, and mangrove fringes provided protective benefits for nearby structures similar to traditional engineering strategies. Damage data collected during a longitudinal study in March 2018 emphasized the challenges faced by recovering communities.