Hotel / car rental
Hyatt regency is Kaanapali which has great facilities and on the south end of the beach at Kaanapali. Close to Lahaina and only 40 mins drive from OGG.
Andaz at Wailea about 30 mins drive fro OGG. I prefer Kaanapali but any amount of nights on Maui is great. As others have said stay in one hotel.
Car rental try Costco, priceline or discount Hawaii rentals.