No, you have to book them one at a time. I book the first one and assign it to my husband as the lead guest (he is on my
MDE account). Then it will let me book the second with myself assigned as the lead. If the same category isn't available, book your next choice, then modify/rebook the first reservation to the same category as your second. There is no penalty to modify/change/rebook/cancel 30+ days in advance.