Hi Shannon, and welcome back to the Disney Parks Moms Panel!
It is an honor to assist you with such an important decision, as both resorts have very special characteristics that might help you choose.
Both of them feature some VERY special and distinct rooms:
Disney's Port Orleans - Riverside has Royal Guest Rooms themed after a royal getaway organized by Princess Tiana. This room is truly magical and may be perfect to surprise your girl. But if she is more excited about pirates than princesses, though, the Pirate Rooms at
Disney's Caribbean Beach Resort might be a great option. To learn more about those beautifully themed rooms, you can read
Jennifer Fickly-Baker's great post on the Disney Parks Blog. Both of them also offer room options with lovely Child-Size Pull-Down beds, and those might also be awesome to accommodate your 5-year old girl.
Their special transportation offers might also help you decide. Because Disney's Port Orleans - Riverside is so close to Disney Springs, you can board a boat at the hotel, cruise through the Sassagoula River and get there for a night out. Disney's Caribbean Beach Resort, on the other hand, will soon be connected to Disney's Hollywood Studios and Epcot through the
new Disney Skyliner. Either way, you can't go wrong: they are both breathtaking.
I hope you come back for more advice before your next trip - we love to help make your dreams come true!
May the magic be with you,
Julie