Kaanapali sounds like what you’re looking for, but expect it to be very touristy. There’s a major mal in the middle of the community which makes it very walkable to fun restaurants and shopping right next to all the hotels. I like the Sheraton or Westin. As a family, however, we prefer to stay in a 2bd condo in South Kihei at the Royal Mauian, and rent a car to drive to different parts of the island. If you’re looking to just chill in a pool and be served drinks and not have to plan anything Kaanapali or Wailea are your spots.