A lift-up cleat assembly includes a base member having an upper plate shaped to abut a mounting surface and at least one normally vertically oriented tube depending from the plate, wherein the tube has a hollow interior, and a retractable cleat member having an upper cleat-shaped head shaped to retain lines thereon, and at least one normally vertically oriented mounting post depending from the head, wherein the post is telescopingly received in the interior of the tube of the base member and is telescopingly movable along a given length of travel. The cleat assembly also includes a cup-shaped retainer located within the hollow interior of the tube base member and having a central portion fixed with respect to the mounting post of the cleat member and an elastically deformable skirt portion that flexibly abuts the tube of the base member, thereby providing infinitesimally small increments of adjustability of the post of the cleat member within the tube of the base member along the length of travel, and wherein the retainer is shaped to allow liquid located within the interior of the tube of the base member to drain therefrom.