An umbrella holder and stabilization system for hands-free holding of an umbrella includes a housing having a plurality of walls that, collectively, define an interior space, and a top wall defining an opening for receiving the handle of the umbrella into the interior space. The system includes a neck strap having opposed ends and a fastener coupling the ends so to form a loop. At least one clamp is coupled to the neck strap that is slidable along an extent of the neck strap and is operable to releasably capture the pole of the umbrella. A belt includes a strap having opposed ends that is selectively attachable about one of a user's chest or a user's waist. A connector strap may extend between the torso belt and neck strap. Thus, an umbrella is secured in the housing and held upright without use of a user's hands.