Yes you can do it, I’ve done it, it’s not like Vegas where you pass a guard at the elevator and flash a key card. Easy, very easy. 2 of you bring up all the luggage, the other 2 go up when the first 2 get into the room and the bag boy has left. also Ilikai has multiple entrances that do not go past the front desk. easy, very easy

Do you think that you are the first persons who ever thought of this? It happens often with teenagers on vacation or spring break. And the hotels are NOT happy with un-registered people staying overnight. There are lots of legal and liability issues involved, as well as what the law calls “defrauding an innkeeper”, or trespass, or some similar criminal charge.

Look, there are plenty of hotels and condos that will rent a unit that is fitted out for two,three or four guests, (I have stayed at some that have two single beds and a fold-out sofa, etc.) So, they know and expect extra people staying in the room and using the facilities. It makes more sense, and is more honest than sneaking around and doubling up in one room.

Cancel your reservation at the Ilikai and rent a condo instead. No one at a condo is going to check room keys and you can probably rent one that will allow four people without an extra charge anyway. You are either going to get caught and have to pay the extra person charge or your vacation will be ruined by you worrying about getting caught and/or sneaking past the front desk with 2 extra people. Either pony up the cash or rent a condo.