Howdy Abigail!
Disney's Caribbean Beach Resort is one of our favorites. We stayed in a Pirate Themed Room last year and as far as my 4 year old boy is concerned, there is no reason to stay at any other resort hotel.
Disney's Caribbean Beach Resort is very large. It's made up of 6 villages and surrounds the 45-acre Barefoot Bay.
In May, the weather will be perfect for some poolside fun. I'm excited for you because the main pool is amazing!!! Fuentes del Morro pool is a zero-entry pirate’s paradise, themed like a colonial Spanish fortress. There are 2 waterslides—including one measuring 102 feet long. Little ones will enjoy the shipwreck play area, complete with mini slides and a crow’s nest.
There are 6 other leisure pools, one in each village, which Guests can also enjoy.
We did not visit Shutters at Old Port Royale (table service) but we enjoyed several meals at the Old Port Royale food court. There was everything from sandwiches to pasta and everyone found something they loved. At one point, the Cast Members from the food court took a break and entertained us all with a line dance. It was great and something my 4 and 6 year olds still talk about.
The atmosphere is fun throughout the resort!!
If you have any further questions about Disney's Caribbean Beach Resort (or anything else as you plan your vacation), please let me know. I'm very excited for you. The resort offers you a vacation within a vacation. It's a tropical paradise that I know you will love!!
Thanks for your question and have a magical day!!