Hi Jennette!
A big group is a guarantee of big fun at
Walt Disney World! You are in for a magical time!
To book five
Walt Disney World Resorts rooms online, you will have to make five separate reservations, because, yes, the website only allows you to reserve one room at time. Your best bet is call a Cast Member at (407) 939-4357 to book your block of rooms. She will help link the reservations together. Also, put in a request for adjoining or connecting rooms. Disney can not guarantee rooms together, but I've experienced they usually manage to put you close.
With a large party, you might find it tricky to secure
dinning reservations, so consider making two bookings of four each instead of one reservation for eight if you are willing to split and sit at different tables.
Wishing you all a wonderful adventure!
Elisabeth