Located on 15 lushly landscaped acres, perched above Wailea's exclusive resort community, within sight of the luxurious Fairmont Kea Lani, and an easy five-minute drive to the beach, this resort operates as a Japanese-based timeshare. Its guests are mostly investors who fly in from Japan to take advantage of their vacation allotments.
The Diamond Resort is Japan's take on Marriott's Beach Clubs found throughout the Hawaiian islands. Technically, Wailea does not allow time-share properties. But, due to Japan's faltering economy, shareholders are frequently unable to use their time slots and, as a result, the well-appointed one-bedroom apartments are rented to outsiders on a nightly basis.
The property is located at the end of the road, and a car is necessary if guests don't want to be stranded. A circular drive leads to the dramatically designed main building, which looks like a cross between a medieval castle and an Empirical Tudor palace, its massive stone construction marked
with beams and bridges hovering over ornate ponds and streams filled with colorful koi. The breezy, open-plan lobby shows tropical influences, while an adjoining pavilion harbors a lounge with superb vistas of Wailea's palm-studded coastline.
Dining is varied, with a well-priced Japanese outlet supplemented by an independent Italian restaurant. The fine dining room has closed, replaced with a new tepppanyaki restaurant now in its place, (open only Friday—Sunday). Two bars sate thirsts, and the poolside grill offers light fare.
Recreational options include a fair-sized pool, an oversized, outdoor whirlpool positioned for ocean panoramas, a sauna, a gym, and a well-rounded spa with a bevy of private rooms reserved for Japanese, German and Hawaiian health and beauty treatments.
Use of the spa, including mud baths is free, though massage costs extra. Golf 
and tennis are nearby. Limited conference facilities and a gazebo popular with wedding parties are on-site. Business services are limited. Parking is free.
The 24 low-rise buildings grace the hillside, each housing four units and connected to the public areas by colorfully planted pathways. Some of the units are far away from the main building, and as a courtesy, staff often transport guests to their rooms on golf carts.
Accommodations are decorated in subdued tropical style, with soft ocean hues, high ceilings, slate, thick textured Berber carpeting, elegant bamboo and rattan appointments and island fabrics. Maintenance is excellent.
Kitchens are composed of refrigerators, two-burner stoves, microwave ovens, sinks, coffeemakers and enough cookware and utensils to feed a family of six. The living areas provide dining tables, sofa beds and paired armchairs. 
Bedrooms offer mostly twin beds (some have king models), and the lanais are nicely furnished. About half of the rooms provide blue-water vistas, though the garden-view units are considerably less expensive. Two TVs, phones with dataports and thoughtful lighting are standard. The contemporary Japanese baths feature small but deep tubs and high-tech toilets straight from Tokyo that may befuddle American travelers.
Room service is limited. Pets are not permitted.
The Hawaiian staff provides plenty of aloha spirit to a largely Japanese clientele, though North Americans are slowly discovering this off-the-beaten-path retreat. Families and couples looking for privacy and an affordable Wailea address will do well here.
