Extreme events have the most adverse impacts on society and infrastructure, and present the greatest challenges with respect to impacts. Information on the status and trends of these events is, thus, important for system design, management, and policy decision-making. In this study, variations in daily and seasonal rainfall extremes were explored with a focus on the southwest Florida Gulf coastal zone for the period 1950–2016. Rainfall occurring on very wet days accounted for about 50% of the seasonal rainfall in the area (regardless of the season), while about 25% of the seasonal rainfall came from extremely wet days except in the period between October and December for which this latter value was about 40%. No significant changes were seen in the maximum one-day rainfall at any of the stations regardless of the time scale. However, there was a significant increase in the number of wet days in the rainy season at Myakka River (p = 0.0062) and Naples (p = 0.0027) and during October–December at Myakka River (p = 0.0204). These two stations also experienced significant increases in the number of wet days in a year. Significant increases in the contribution to rainy season rainfall from very wet days (rainfall > 25.4 mm, 1 in) were seen at Arcadia (p = 0.0055). Regional results point to an increasingly wetter climate with increasing contributions from extreme events in some areas, both of which have implications for design and management decision making.