I've never had speakers outside by the pool and now I'm starting to think it may be a great idea to install some there. What do you think is the best place to position them where they won't get wet or damaged?
I think that will depend on how big your pool area is. I read in an outdoor speaker placement guide that you're supposed to have a speaker to cover each zone in your outdoor area, ideally.
Honestly, I would be a little worried to have anything permanent set up outdoors because not only is there the pool water to contend with but weather and whatnot. I just use portable waterproof bluetooth speakers.
I reckon that would depend on the kind of setup you have around your pool. Are there any covered areas? How large is your pool? I think Aria's suggestion would be your cheapest solution.