A sealing grommet assembly for use with a panel and a wire bundle includes first and second grommets, a cable guide, and an annular retainer. The first grommet defines a first conduit and a first set of sealing lips. The second grommet defines a second conduit and a second set of sealing lips. The cable guide is positioned within the first and second conduits, and receives and supports the wire bundle. The annular retainer is encapsulated by the first and second grommets, and has a first set of axially-projecting latch fingers that secures the first and second grommets to each other. The retainer also has a second set of axially-projecting latch fingers that secures the first and second grommets to the panel. The sealing lips form a seal against opposite sides of the panel when the sealing grommet assembly is secured to the panel via the annular retainer.