Original Message:
A few thoughts... (by KC):
Your post might get deleted by a Moderator if it is determined that it should instead be placed as a (paid) "RedWish" ad. The forums are for discussion, not for conducting business. If your post is not removed however, a few generic observations follow:
1. Keep in mind that, more often than not, a resort will clearly specify a maximum legal occupancy of 6 people for a 2BR unit.
2. Good potential rental sites include RedWeek, MyResort Network. Go the specific geographic area of interest on either site and read through what is advertised as available. You will also then see whether your identified "maximum price" is realistic or achievable.
3. Rent ONLY directly from a confirmed owner (call the resort to confirm owner identity, once provided to you by the owner). Execute a clear, specific and detailed rental agreement with that owner, one which clearly identifies dates and times, unit size and identification, payment terms and a cancellation policy. The chances of someone trying to improperly rent out an exchange are lower in Hawaii, since it's very tough for anyone to "trade into" Hawaii in the first place. If they got the trade, they'd likely use it (not try to improperly rent it out), since they would have had to "deposit" (give up) something pretty darn good to get that "exchange" in the first place.
4. In general, Hawaii is regarded as "red" time all year round, so there is less "seasonality" to demand there. There are rarely any real "deals" to be found, even with airfares sometimes being crazy high. You don't have a whole lot of "area" choices in regard to "different parts of the island" on Maui, since the timeshare resorts are somewhat concentrated in about three general areas (Lahaina, Kihei, and in between the two).
5. Finally, an owner might require (and has every right to require) proof of age (generally specifying 25 years of age minimum for any non-family group). Owners (and the resorts themselves) are often not enthusiastic about occupancy by groups of "college agers", for very specific example.
Hope some of this helps you a bit. Good luck.