I booked a partial ocean view room. But since the hotel was crowded, I had to put myself on the waiting list for a better room (I have no problem paying for the better room to guarantee it, rather than hoping for an upgrade). But it looks like nothing came through and I'll be checking in tomorrow.

Now when I check in, say a better room becomes available. What do you think the hotel will do?

1. Offer the upgrade as complimentary.

2. Since they see that I was on that waiting list for a better room, tell me it's available but at the higher price.

No one knows but the desk clerk.

Look like the kind of person they would like to upgrade and be nice but not schmoozy.

Sounds like the hotel will be full, which means they will have limited ability to move people around among rooms.

Unless they think they will have a better shot at selling your room than the higher priced room to a walk-up, you won't get an upgrade. You might not even get off the waiting list at the higher price if they expect to be able to persuade a walk-up to pay full freight. They've already got you in the house, you don't have to be lured into staying.

Interesting. I hadn't thought of it in that light. I would think a nice resort would not have that much walk up business, but I guess that's a possibility.

Well,if the hotel bothers to keep a waiting list, and you are willing to pay for the upgraded room, why wouldn't they give it to you?
Very rarely are hotels 100% full and if they can charge you for the higher room and possibly leave a cheaper room vacant, that would be better for their bottom line.
Let us know what happens.

I just checked with them a couple days ago, and they said still no availability for the better rooms, so I'm assuming they are really full, or as a previous poster suggested, they think they have a better chance selling the better room to a walk up guest then the room I've been booked into.

I don't know if they're holding rooms in reserve for some reason, but either way, I doubt one would just happen to open up (or they would release one) the day I check in.

The hotel is sold out of the better room. If the better room becomes available on the day you arrive then the customers on the waiting list will get them before they offer the comp upgrade.

when you get there, just remind them that you wanted/tried to book a better room and do they have anything available, or will something become available. I'm sure i don't need to tell you to just be very nice and polite. When we went to bermuda years ago, we went through our amex and were to get an upgrade "if available". when we got there there was no upgrade available. I chatted amiably with the front desk employee and later on when we checked int (we had arrived in the a.m.) he called me over and said "we have a room, it has no shades yet, but it is a 2 story ocean front presidential suite" and we could have it if we wanted it. It was the nicest hotel room we have ever stayed in. So, you just never know...

Perhaps I shouldn't have used the "walk-up" terminology, but what I meant was something along the line of some high roller who makes a last-minute decision to go to this resort. Especially if they have an established relationship with the place, they will take precedence over you.

But others are right, it NEVER hurts to ask, and one ploy is to ask if any of the better rooms might come open later on in your stay and indicate a willingness to move. We've lucked out that way.