We go to Maui almost every winter. Last year I took my bike and did Haleakala.

A few thoughts. Maui is a relaxing beach destination (at least for us). All the "big hotels" are right on the beaches. I tend to like houses and condos also but not in Hawaii. I would rather have the beach a few feet out my front door and that basically means a big hotel.

I was also a litle frustrated biking on Maui with the traffic. The "upcountry" is great but the traffic on most of the other roads was a lot heavier than I am used to. In fact, there really aren't that many roads on these islands. I don't think I would even bother bring my bike there anymore (but glad I tried it once). From now on, my winter biking vacations will be in places like San Diego, etc..