Yes - pictures would help! My thoughts are along the line of
local "floating docks" - the ability to go up and down with water level without human intervention - is normally accomplished by a large post sunk into the bottom of the ocean, with a frame around it that can slide up and down. I'm not that knowledgeable about "Beer Keg Coolers" so please elaborate:
1) is the goal to keep the whole cooler under water or only the bottom of it?
2) if you're worried about occasional freezing weather, is it light
enough to be moved elsewhere during high-risk periods?
3) how important is it to keep it upright?
4) how buoyant is it? - Is the issue going to be keeping it under, rather than keeping the top dry? The type of cooler we have would float like a cork. I suspect you're going to want some sort of anchor on it either way.
5) Is it sealed well enough not to attract vermin?