Region: Maui Island

Words that describe this place are: wow, huge, awesome, overwhelming, crowded, fun. Grand Wailea is indeed one of the largest resorts on Maui. They took every dream and whim that the designers could come up with and sprinkled in a half billion dollars or so (give or take a hundred million—I mean, who’s counting when it gets that high?). The result is an outrageous, exotic tropical playground.

When you drive up, you are greeted by a waterfall that would look natural along the road to Hana. (In fact, one of the tour companies shows this waterfall in their jungle tour of Hana brochure—shame on them.) Once you’ve checked in, you just gotta check out the pools. Imagine nine interconnected pools with a current running between many of them. Waterslides, Tarzan rope swings, rapids to shoot, a sandy baby beach portion, and a swim-up bar. This pool is wildly popular, and you’ll be forgiven if you sometimes wonder if everyone staying at the resort has decided to hang out at the pool for the day (quiet, it ain’t, even at the adult pool). The chairs are very tightly packed around all the pools.

Speaking of chairs, if you rent the cabanas at the pool, it’s among the most expensive in all of Hawaii in peak season. And you should reserve it in advance. But hey, they sure do pamper you. They’ll serve you water, popsicles and fruit. We think for those prices they should at least include a personal masseuse. Casabella chairs are also available per day by the pool and on the lawn by the beach. At least the umbrellas and chairs are free.

The 40 acres of grounds do hide lots of nooks and crannies where one can find some privacy. They are more smoker-friendly, in that the areas where you can smoke feel less like a punishment and more like a pleasant spot to enjoy a cigar. Over $30 million worth of art—some beautiful, some bizarre—adorns the grounds and lobby.

Countless shops are here, mostly upscale. They have numerous restaurants. Wedding services here are extensive. They host gobs of weddings each year, and their chapel is utterly gorgeous.

Grand Wailea is blessed with being located on one of the finest beaches on Maui—Wailea Beach. Endless frolicking fun is yours to be had here. They have windsurfing lessons, snorkeling and boogie boarding accoutrements for rent and scuba lessons. The latter take place in their dedicated scuba pool, which is 10 feet deep and lined with sea critter tiles. They also have indoor racquetball and basketball in the fitness center along with fitness classes (for a fee).

The day spa, like everything else here, is huge and busy. Every bone-melting treatment that the human race has created seems available here for every member of the family.

The rooms are nothing special when compared to other resorts in Wailea, but they have what you need. They have what we call a “close family fee.” If you want to use that door connecting adjacent rooms, it’s an extra fee per night. (Ridiculous but true.) They say it will guarantee you a connecting room.

We’ve been to this resort a number of times over the years, and though we’ve liked it a bit less each time, the staff seem to have improved on this visit. Still, we found it felt more like a visitor-processing machine than a warm, welcoming resort.

Grand Wailea can feel like Disneyland on the beach. It’s one of those places where you can hang out at the resort and stay entertained for days. (Which, of course, we hope you won’t do.) What’s the catch? Wadayatink? The price. Rooms are 640–715 sq. ft., suites are 1,300–5,500 sq. ft. Packages may alleviate some of the rate pain.

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 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 are 1,900 sq. ft., penthouse 3/3s are 2,100–3,100 sq. ft., villa 3/4s are 3,100 sq. ft. Discounts may be available (and much welcomed). 3- or 10-night minimum. 

This is the only major Wailea-area resort that’s not on a sandy beach. The property sits on a rocky, elevated stretch of shoreline, but two corners of it are adjacent to beaches (the lovely Wailea Beach to the south and Ulua to the north), and the sand is easily accessible with a short walk. The resort’s buildings are spread out over 22 acres of rolling green lawns that never feel crowded.

Five pools, including an adults-only infinity pool (no talking on cell phones allowed) and an adventure pool with waterfalls and four waterslides. One of those is 325 feet long (currently one of the longest resort waterslides in Hawai‘i), and another is 240-feet. A real blast— great for kids and kids at heart.Generous room designations: Many “garden view” rooms have ocean views, and many “ocean view” rooms would count as “oceanfront” elsewhere. The rooms themselves seem a little sterile following a major renovation. They’re light, sleek and contemporary, but lack a Hawaiian feel. Overall, though, the resort evokes a relaxed feeling. More upscale than what you’d normally expect from the Marriott brand.

They actively seek the family market (with a seasonal, if available, children’s program) and the group market (with many conference facilities). There is also a family game room and cinema with beanbag chairs. Mandara Spa is on site. Cabanas for rent at the pools, some may let you stay until 7 p.m. to watch the sunset. Covered casabellas by the ocean are also available for rent.

Rooms are 437 sq. ft., suites are 463-2,123 sq. ft. Lots of packages available.