Wailea is more a collection of places to sleep (resorts and condos) and their gorgeous beaches, with some nice shopping and restaurants and golf to support that. In fact, Wailea was built as a tourist community and isn't a town, per se. (The town next door is Kihei.)
Lahaina is a proper town and feels more like it. Bigger, more bustling (though it's all relative! It's still got the slow, island feel -- nothing at all like, say, Honolulu.)
I have always stayed in Wailea, and absolutely loved it. We mainly relax on the beach and eat dinner out and don't mind driving a bit to get to the "touristy" activities like horseback rides, Iao Valley, Haleakala, shopping in Lahaina, etc.
Ahhhhhhhhhhh. I want to go back. Not in the cards for a while.
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