Hello Amy, As a planner for a family of 5, I feel your pain! If your heart is set the Caribbean Beach Resort you will indeed need two rooms due to the maximum capacity of 4 per room.
What we have done in the past is either book 2 rooms at the All Stars or Pop Century or 1 room at a deluxe resort. If staying at a value, adjoining rooms are guaranteed if the children outnumber the adults. This option is convenient as you'll have two rooms with two bathrooms and two TVs. The option we tend to prefer is staying at a deluxe resort that will accommodate 5. These rooms include two queen beds and a day bed. You also have other options that include the family suites that are available at All Star Music or the cabins at Fort Wilderness will also accommodate up to 6. I hope this helps get you started. Let us know if you have further questions. Diane
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