If you are going to spend the money to fly the family to Hawaii, you might as well go the extra mile and live in style while you are there. Located in the middle of a golf course, these Waldorf Astoria–owned villas offer stunning views, massive decks, high-end kitchens, and access to perfect beaches. With three large bedrooms spread out over two floors, you can escape from the kids when you need a break. A bonus: While you are there you have full access to the adjacent Grand Wailea hotel’s numerous pools, waterslides, restaurants, and spa.
Nightly rates start at $1,400 with the seventh night free. You can reserve here.