Yes, there's usually music by the pools, not overly loud, mostly beach and pop music from the '60's to the present, sometimes Disney tunes too. We like that, then we haven't had to listen to blaring music from other guests. Yes, you may bring a small cooler. No glass or breakables poolside. The kitchens at CWBC are stocked with a few tall, hard plastic tumblers (drinking glasses). We've sometimes brought those down to the pool with us as well as to the picnic/BBQ areas.