Being strongly influenced by the landscape of the Red River Valley, geophysical and a variety of sociodemographic and economic factors, the characteristics of floods are complex in the Province of Manitoba, Canada, which causes substantial loss and damage to lives and properties. The primary objectives of this study are two-fold: (i) to identify the geophysical and human-induced conditions of floods, and examine the trend in flood loss and damage in the Province of Manitoba, Canada; and (ii) to analyze the social vulnerability perspectives of floods in the Rural Municipality of St. Andrews, as a local community case study. Using the Delphi technique, primary data were procured from the field for community-level vulnerability analysis. Secondary data for a provincial-level analysis were collected from various public domains, including governmental departments and other non-government sources. The results reveal that a nested set of geophysical and societal factors determine the degree of vulnerability of individual community members. In Manitoba, it was found that socioeconomic damages caused by floods have increased considerably over time despite undertaking costly structural flood mitigation measures. We conclude that minimization of flood damages requires complementing structural measures with knowledge-sharing, collaboration among pertinent institutions, and the adoption of an interactive flood management system approach.