We stayed at Catcha a week or so ago and getting floaties in and out of the water was no problem. A cooler could be done but would make it a little more difficult depending upon how many beverages you have in it to weigh it down. No shade while in the water (ocean) but you could float in the pool and there is a bridge you could stay under that could keep the sun from beating on you. Have a great trip!! You will LOVE Catcha!! Many private areas to lounge too!