Hi Kelly,
Welcome to the Disney Parks Moms Panel. I trust that everyone is excited about the upcoming trip!
Disney's Caribbean Beach Resort and
Port Orleans Resort - Riverside are beautifully landscaped resorts. As moderate resorts, they both have similar amenities. Both have a jogging trail, Table-Service restaurant, playground area and multiple pools. Disney's Caribbean Beach Resort has one main pool with two water slides and six leisure pools. Disney's Port Orleans - Riverside has one main pool with one water slide and five leisure pools.
Disney's Port Orleans - Riverside does have two transportation options (bus and water taxi) unlike Disney's Caribbean Beach Resort, which has only one (bus). Water taxis at Disney's Port Orleans - Riverside transport guests to Disney Springs. Disney's Port Orleans - Riverside also offers horse-drawn carriage rides.
I do think it is worth noting that Disney's Caribbean Beach Resort is currently undergoing refurbishment. This refurbishment will particularly impact the Trinidad South region of the Resort. In fact, during the refurbishment, the Trinidad South Village pool will be closed.
Each resort is lovely and the decision really depends on your family's preferences. I will say that I appreciated the rooms at Port Orleans - Riverside a bit better because the decor seemed more muted. I hope this information is helpful as you contemplate your options.
I trust that you will have a magical time no matter which resort you select!
-Donyell