That's interesting about Starwood trying to coax you out of using an award. Obviously Starwood places some internal value on an award night and "credits" that hotel something less than $250/nt. for the stay.

It wouldn't bother me too much. For $400/nt on Key West, I'm guessing you are talking New Year's Eve (or similar). It's still a GREAT use of hotel points because Priceline would likely yield NOTHING and even junk like the Fairfield Inn wants $175/nt.

I have done 2 New Year's trips to Key West. Once we stayed in a BAD room at the Marriott (which is no longer a Marriott IIRC) for $259/nt. and the other time we stayed in a little cottage we found on the Internet for $180/nt. The little cottage was wonderful, and we realized that Key West is a good place to forget about the chains UNLESS you are redeeming an award.

Whoever you talked to at Molokai sounds like a mean-spirited person. I don't think that's a reflection of the entire chain. I've run into nasties at the front desk of all of the big chains. FWIW, the Molokai hotel will no longer be a Starwood soon, according to some threads here on FT.