I've rented boats in the keys from several different places and for the most part it's gone pretty well. It sounds like you're not trying to do anything to crazy and really won't require a big(ish), expensive offshore rig (which are available). If the goal is to spend a day or two near shore bopping around with the kids I think I'd rent. That’s a long haul to only drop your boat in a couple times. That said... if you're place has dockage and you'll be able to conveniently use your boat everyday for a week that’s different. I'd haul it down in that case. Really a matter of how many hours you plan on spending on the water.