Never stayed yet at the Hilton FL but have a few times at The Dip. If you want to be walking distance to a street hangout then the Hilton wins since Los Olas if I remember is walkable. While The Dip will require a long drive to SOBE or anything like Los Olas

The beach area by The Dip is pretty narrow and by the Hilton its wider, but the Ocean is too cold to go into this time of year anyway anywhere down there