So winter is really upon us, it's getting cold and wet (thankfully wet here in CA) so now is a great time for a short getaway to Hawaii. You can still find sub $600 Airfares from the bay area in January. And some availability for rooms.
One of my favorite spots is Napili Beach which is between Kaanapali and Kapalua, its not always easy to get a place to stay here as it's so popular , so the best alternative is for those on a budget is the Ka'Anapali Beach Club ( not beach hotel ) which is a diamond resort property. Its very well located and not too pricey, and not too dated, rooms from $230 a night, or for those looking to go big the Ritz Carlton at Kapalua is a good option as there is a free on demand shuttle to Napili beach which is a stunning beach.
I highly recommend the following places for eating :
Hula Grill and Leilani's on the beach at Whaler's Village in Ka'Anapali
Fleetwood's and Honu in Lahaina
Seahouse and Sansei Sushi in Kapalua
Also unless you are going to do lots of exploring of the island, i would not bother with a rental car, it's much cheaper overall to book a taxi to and from the airport, and use Uber to get from place to place, as many hotels charge a large parking fee, and this plus rental costs far exceed your taxi and a few Ubers to dinner.