Sure Seal connectors have a line that goes up to 10 connections,
http://www.suresealconnections.com/index.html
these are very reasonable, I pay a few cents per pin, and about 2 dollars a boot, male or female ( the boot, you can put whatever gender pins in either side.) . These are very durable, similar to a spark-plug boot, never had any sealing problems. I use them on heavy equipment and transport trucks. If need more than 10 positions I often just use 2 plugs. Generally I will separate power and signal into plug sets. Often this ends up saving space, believe it or not, since you can place two 3/4" plugs side-by-side, so vertical space is saved, in the over all diameter.
For more poles, I usually go with a Packard type connector. These are the ones you see on cars today. They come in every combination you can think of, from 1 to 100 or more pins. They can be a hassle with all the parts involved, pins, boots, seals, grips, shells, bodies, tails, etc, but they are completely sealed, guaranteed.
Common types of these are Metri-pak, Weather-pak.
AMP and ITT canon also do a line of CPC ( circular plastic connector, aka the old military style bayonette type plug ) connectors that have a myriad of pin options. They come in a sealed version also. Lots of places carry them. They are not too bad in price. This is what is in the picture above, basically. You can always just get a plain old CPC plug, and smear a load of dielectric grease on both sides, and you get a sealed plug. Not the nicest thing to work with , but tried, tested and true.
Mouser does these:
https://www.electro-tech-online.com/custompdfs/2004/11/797.pdf