Meghan:
Although your family could technically qualify for one of the rooms that sleep 5 with the new trundle bunk at Port Orleans, make your final decision on how much time you'll actually spend in your room. When 5 of our family stayed at
Port Orleans: Riverside, we loved the resort, its access to Downtown Disney via boat and its Ol' Man River pool area, but I have to tell you, we used up every square inch of our room and we had two adults and 3 elementary-age children for that trip in comparison to three adults in your party.
Having two rooms, even at a Value Resort, can seem like a luxury: two bathrooms and almost double the space of a moderate room like those of POR feels like a bargain for the $30 or less that you'll pay additionally. Because you use bus transportation for both resorts, that remains equal.
Pop Century's iconic statues give off the Disney-feel to which so many children respond. POR has a more subtle theme that will appeal to adults. POR, though, has the better food court and restaurants, but again, if you're not spending much time at the resort for meals, it doesn't make up for everyone getting their own bed at night at Pop.
If I were making the reservations, especially if one of the adults felt like they needed extra privacy when getting ready in the morning or at night, I'd choose two bedrooms at Pop and ask for the rooms to be connected. Although Disney doesn't guarantee connecting rooms, they do their best to make accommodations.
Wishing y'all a magical vacation!
Whitney