The only schools I'm personally aware of that go to Florida (and this is Lexington schools) have the trip completely paid for by the booster club. Now, where does the money come from in the booster club? It comes from fundraising or out of a parent's pocket if they choose to not participate in fundraising. The players even get meal money every day. I've never known of a kid not being able to participate or travel. I can't imagine a coach saying that kids have to come up with money out of their own pocket.
Now, for families that would like to attend that's a different matter of course. It is understandable that some players will end up down there without family present. Of course, some players are playing right on their home field without family support. There are always unfortunate circumstances that surround highschool athletes of all sports. One difference between the boosters of larger schools vs those of small schools/communities is the available fundraising of course. It's much more difficult for a school of 400 kids in a small community to have many options.... at least not the options of a school of 2200 in a city of 350,000.