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3800 Wailea Alanui Dr, Wailea
Finished in 2006, these luxury gated condos are so exclusive that you need a key to both get in and out of the resort and the elevators. It’s adjacent to the Shops at Wailea and the Grand Wailea Resort (you can access both with a provided key). It consists of eight buildings, including a 5-story building that contains the “penthouses,” and seven 2-story buildings housing the villas. Penthouses are farthest from the ocean, and views are best from the fourth floor or above. Villas A and B are closest to the ocean.
The contemporary Hawaiian-style buildings have lush, tropical grounds with lots of mature plants. Though not directly on a beach, there is a meandering stream that leads to the beach path and a short hop to Wailea Beach where they have umbrella chairs. Their adults-only pool is a peaceful infinity-edge pool. Their family pool has a small waterfall, a shallow end for keiki, billiards and game room. Ground-floor villas have their own tiny plunge pool with a waterfall and an outdoor shower, but no ocean views. The rooms themselves are ultra-luxurious and expensively furnished by different interior designers. The bathrooms have deep soaking tubs and separate showers. The kitchens use all top-of-the-line appliances, granite counters and Viking BBQs on the lanais.
The on-site concierge has extra services such as various food packages with local specialty items, fresh flowers, wines and spirits, special event cakes and rental cars available. Other services can be arranged by the resort (for a fee, of course) such as personal trainers, personal secretaries, au pairs and private chefs. But at least the cabana chairs are free by the beach.
If you’re worried how much this will set you back, then you probably can’t afford this place. If you do stay here, however, and you’re unhappy for any reason…then there is just no pleasing you. The staff is very competent here. Penthouse 2/2s (1,900 sq ft.) start around $1,400, penthouse 3/3s (2,100–3,100 sq ft.) start around $1,600, villa 3/4s (3,100 sq ft.) start around $2,400. Discounts available (and much welcomed). 3- or 10-night minimum. Note that in addition to the daily resort/service fee of about 6%, you are also charged a one time reservation fee.