Large satellite discrepancies and model biases in representing precipitation over the Southern Ocean (SO) are related directly to the region's limited surface observations of precipitation. To help address this knowledge gap, the study investigated the precipitation characteristics and rain rate retrievals over the remote SO using ship‐borne data of the Ocean Rainfall And Ice‐phase precipitation measurement Network disdrometer (OceanRAIN) and dual‐polarimetric C‐band radar (OceanPOL) aboard the Research Vessel (RV) Investigator in the Austral warm seasons of 2016–2018. Seven distinct synoptic types over the SO were analyzed based on their radar polarimetric signatures, surface precipitation phase, and rain microphysical properties. OceanRAIN observations revealed that the SO precipitation was dominated by drizzle and light rain, with small‐sized raindrops (diameter <1 mm) constituting up to 47% of total accumulation. Precipitation occurred most frequently over the warm sector of extratropical cyclones, while concentrations of large‐sized raindrops (diameter >3 mm) were prominent over synoptic types with colder and more convectively unstable environments. OceanPOL observations complement and extend the surface precipitation properties sampled by OceanRAIN, providing unique information to help characterize the variety of potential precipitation types and associated mechanisms under different synoptic conditions. Raindrop size distributions (DSD) measured with OceanRAIN over the SO were better characterized by analytical DSD forms with two‐shape parameters than single‐shape parameters currently implemented in satellite retrieval algorithms. This study also revised a rainfall retrieval algorithm for C‐band radars to reflect the large amount of small drops and provide improved radar rainfall estimates over the SO.