What time of year? Summer is very difficult to impossible.
Lower seasons (fall, winter) possibly right at the 7 month window but no guarantee. Absolutely not for summer. There are a total of 21 lockoff 2BRs at HHI. (So, 21 studios or 21 1BR). The resort is mostly 2BRs.
We generally go in October. It's usually in the 70s during the day. Pleasant, not hot, but not really beach weather for us. The ocean always seems cold to me then.Naturally, we don't want to be miserable at the beach in Jan or Dec, but we could certainly do a Spring or Fall trip. We'd want it to be comfortable but it does not have to be summer.

We generally go in October. It's usually in the 70s during the day. Pleasant, not hot, but not really beach weather for us. The ocean always seems cold to me then.![]()
Early May would be nice. We were there around the middle of May last year, we own there, but as long as you do not hit spring break time, it could happen.

I got studio HH for this June at the 7 month mark. Never know.