Ja, just getting back from 10 nights (Christmas and New Years) at the Grand Wailea. And I was just pit stopping to tell a little about my stay, and now I see I can book again for the end of the year
Thanks for the alert drekin !! Just got in again for New Years
2022/2023
Clarification: after landing on a Red Eye from Vegas, I just made two reservations back to back (my SO and myself) for 5 nights each, starting on December 22 and checking out on January 1st, 2023. At the beginning, even though Amex transfers to Hilton immediately, the system wasn't recognizing the new balance, although it clearly showed it. But after a couple minutes, it did, and the two double beds option for 380K HH Points worked. This year past year (12/23/2021), we were upgraded as Golds to an Ocean View room for the 10 nights, so maybe we can score the same upgrade next year
I used to go to the Marriott Wailea next door, and did for 2017, 2018 & 2019 during New Years. But you can't beat the Hilton, as Marriott does charge a Resort Fee even with points, they only give you a crappy Starbucks coffee, pastry and cup of fruit as Titanium and never upgrade you even to partial ocean view. In the past, I only booked with them because the total points for 5 nights was super cheap. This year not only do they want an insane amount of points in their own currency, but they are about to switch also to dynamic pricing in march, which, of course, makes the Grand Wailea a no brainer.