Jonathan,
Try a couple of the big, black tool boxes they sell at Home Depot, and Lowe's. They're call "Tough Boxes", and yes, they are. The ones I bought cost $44 each. I put two of them on my Nacra trailer, and they have worked out great. I use one of them to store all my wet gear when we finish up and head home. It keeps it out of the van, and lets evrything else stay dry. Plus, you can lock them. I've had them on my trailer for about two years. I "U" bolted them on the tongue, and cross braces. I made my own "U" bolts out of flat bar and 3/8" bolts, and siliconed the washers where they bolt through. I agree that holes in the bottom will drain, but it will also let water in while driving down the road when it is raining. You may want to keep what's inside dry -- like tools, etc. I've never had problems with water inside, and they've stayed dry whenever it rains. I just leave the top cracked open when finished and any moisture inside dries. (No, I don't leave the wet gear inside the box.) I'd be glad to send you a picture if you're interested.
Good luck,
Don