Abstract: An umbrella anchoring system for selectively supporting and anchoring an umbrella to an anchoring surface, comprising a supporting sleeve having a supporting cavity adapted to selectively receive and support the umbrella, and an anchor adapted to detachably connect to the supporting sleeve. The anchor is affixed within an anchoring recess formed within the anchoring surface, and holds the supporting sleeve in a position perpendicular to the anchoring surface. The supporting sleeve may further comprise a tightening assembly which locks the umbrella within the supporting cavity. The supporting sleeve may be detached from the anchor when the umbrella is not in use, leaving the anchoring surface free of obstructions. The umbrella anchoring system may further comprise a base cap which covers the anchor when the supporting sleeve is detached from the anchor.