Banking and vacations

I’ve got the vacation plan for November, back at the same resort in Jamaica. The payment for it was due at the end of August. I was a little behind schedule so I withdrew the USD funds from my account into a money order and had it Federal Expressed to New York on the 29th.
A week later I got an email asking where it was.
I checked the tracking number. They had apparently received it on the 30th. I even got the secretary’s signature saying they had received it. I brought this all to their attention, and they still couldn’t find it.
So I had to repeat the process.
The thing is that you can’t cancel a money order. You can only tag it saying that it shouldn’t be cashed at the bank. You then get the money back, but it feels like a mortgage application because they want you to be able to cover the funds if some bank accidentally does cash it.
So I’m taking a risk here, but I don’t see what other choice I have. I already have the plane ticket, so I’m going.
Yesterday I got a replacement money order made, and I sent it by express post today.
Hopefully things work out this time.