This sounds amazing! I want to do Hawaii in 2020, possibly Christmas time. I've never been. My plan is similar to use Marriott points, and also stay at Aulani hopefully with DVC points for 3 nights. I recently canceled my trip to Ritz Carlton Grand Cayman and want to save the points for Hawaii. I will also have Southwest CP, so hoping I can utilize that as well. How far in advance can I look into booking the hotels? Any advice for me? I have approx 375,000 Marriott points.
Which island?
Marriott releases room availability 50 weeks (about 350 days) in advance, usually in chunks of 5 days or so at a time. So if you have dates in mind, start checking about a year out. Currently, I can book out to 1/10/20 (351 days from now), but if I needed to check out on the 13th, I’d wait a few more days and keep checking. If you have your dates, there’s really no reason for you not to book ASAP because all Marriott hotels should now offer the points advance option that lets you book an award reservation whether or not you have enough points in your account. Remember, with award reservations, your 5th night is free.
I’m pretty on top of making reservations, so I tend to jump on them as soon as they’re released. But even during the busy Christmas and New Year’s period, I’m still finding award availability at all the Waikiki Marriotts (except the 35k/night Princess Kaiulani) almost two weeks after rooms were released. I’m seeing award availability at the Westin Ka’anapali, Ritz-Carlton Kapalua, and Sheraton on Maui, and availability at several hotels on Kauai, too. Last year, I think I made my award bookings for the Royal Hawaiian and Sheraton Waikiki in early April. Don’t wait too long.
I’d note that Marriott is planning to introduce peak pricing in, I believe, March, which may impact the points pricing during Christmastime. For Marriott’s category chart with standard, peak and off peak pricing, see:
https://members.marriott.com/redeem/ However, all Marriott hotels should now offer points advance, which allows you to allows you to book an award reservation whether or not you have enough points in your account, provided you have the points by two weeks before your check-in.
Hope this helps. And I can’t wait to read about your Hawaii plans!