FYI, there are currently three 4.5* properties in Wailea. They are the Fairmont Kea Lani, the Grand Wailea, and the Andaz. They all cost quite a bit more than the 4* resort properties, which are the Makena Golf Resort, and the Mariott Wailea. Non-opaque rates for the three 4.5* resorts are typically $450 or more per night, usually at least $150 per night higher than the Makena Resort and the Marriott. Frankly, if you got any of those three properties for $250 per night, it would be a screaming great deal, although I personally am not a fan of the Grand Wailea because it is vast and massive, the other two, being the Andaz and the Kea Lani, are spectacular. But you are by far most likely to win the Grand Wailea if you win any of them. And it would certainly be expected to cost you more than a $50 premium per night over the Makena Resort or the Marriott. Whether or not it's worth it, depends upon how much you like the Grand Wailea and it's massive scale - personally, I'd prefer the Makena Resort for the $175-190 it usually goes for.