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Chief
My fiancé and I recently stayed in this Airbnb and liked it! Nice hosts, very walkable location, parking, and had all the basics we needed. https://abnb.me/JlaCY0NNVpb
We have a condo in Kihei and go at least once a year. Stay in Kihei for a good local vibe, Wailea for more luxury, and Kaanapali for more of a resort/hotel/party district feel.
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We stayed in one of the condos in Polynesian Shores. Its beautiful and access to the hot tub was especially great! You have a great view of the ocean from the garden. Good hosts and clean house.