Pros: comfortable rooms, fantastic public areas, nice adults-only pool
Cons: not enough (non-valet) parking, rip-off "resort fee"
I stayed here with my wife for 8 nights in January '06; my previous stays on Maui had been on the Kaanapali (West Maui) side of the island, and driving to Wailea it seemed rather dry and barren. The resort area of Wailea is, however, simply amazing ... what a few billion dollars will do. My first impression of the hotel was that it was indeed grand but a little over the top in that Disney meets grandiose Vegas sort of way, but this really faded after a day or too and the place seemed warmer and less sterile once we became familiar with it. By the time we left we felt very happy with our choice.
ROOMS: We had booked a deluxe ocean view room, and ended up in the Haleakala wing on the 8th floor (rooms are on floors 4-9). Our first room was an inside corner room where the wing makes a 45 degree angle, and this meant that the balcony narrowed down to 2/3 the size of a non-corner room, creating a tunnel effect on the view. After 2 nights we were able to move 3 rooms over and this helped tremendously. For real ocean view you need to be on the 8th or 9th floor (at least in this part of the hotel) as the palm trees,etc are tall enough to partially or completely block the view from the lower floors. Also, you need to know that the hotel is set back fairly far from the ocean for most of the rooms - there are two wings closer (lagoon and Chapel wings)but they are only 4 floors high and again most rooms would seem to have a garden view or partial ocean view at best. I was initially disappointed with the rather distant "deluxe" ocean view, but this faded after the first couple of days, and we could hear the waves at night with the door to the lanai open.
The room itself was very comfortable, with a great bed and a muted tropical decor. The bathrooms are large with a glass enclosed shower and a deep soaking tub; the first room had an all-marble finish and the second had white and terracotta tile with greenish wallpaper. Initially we felt the tiled bathroom was a disappointment (ie less luxurious) but ultimately I liked it better as it had a less generic feel and was more tropical (sort of Caribbean). Some reviews seem to let small problems ruin the entire stay for the writer - for example, our first shower's drain was plugged and we were in ankle-deep water after a few minutes, and one of the lamps didn't work. The maintenance staff fixed both promptly (as they should) so no problem. It's a 700 + room hotel - everything can't be checked between customers, the question is whether the hotel fixes the problem quickly.
PUBLIC AREAS: This is where the Grand Wailea shines - the pool area is a lot of fun, and not just for kids. The longest water slide is kinda intense (especially the first time down before you know what to expect), and the canyon pool area is as good as any and better than most. The swim-up bar is in a faux-cave; kinda neat but in January it can get a little cold in the water when out of the sun - I kinda wish they hadn't stuck it in a cave when the outside area is so great. A NICE feature is the Hibiscus pool - adults only and the water is significantly warmer. Overall, the grounds look and feel the way a luxury resort should; again it depends on what you are looking for - it IS a bit Disneyesque but definitely not overly so, but enough to be fun and playful, but for those searching for the quiet tropical hideaway this may not be your place.
The beach area is excellent - the best in the area. Wailea gets a little windy in the afternoons (at least in January) and the wave action picks up but was not prohibitive to anyone except very small children. This is good for those interested in body surfing, boogie boarding, etc. Snorkel in the morning to get calmer water. There is also an excellent 1 1/2 mile beachfront path for jogging, strolling, etc and the GW is about in the middle of this.
RESTAURANTS: Humuhumunukunukuapua'a (the lagoon-side seafood place) - we had an excellent meal there with fresh seafood, well-prepared appetizer and salad, and an expensive winelist but with some reasonable choices. Service was good - I got a watery gin & tonic that was promptly replaced with an apology. Roving musicians playing soft Hawaiian music non-intrusively was a nice touch.
Bistro Molokini: nice, classy place for lunch or dinner; made a light meal there one night of assorted appetizers to share, and all were excellent.
Kincha: the one sour note in the Grand Wailea; the most expensive of the restaurants, and it felt like a cheap Japanese restaurant with chintzy decor, poor placement within the hotel, and the food was expensive and nothing special. My wife had sushi that was average only, and I had a "special meal" consisting of tempura, sushi, and filet mignon + lobster. The "lobster" was tiny, tough and absolutely flavorless, the beef was good but consisted of a scrap finished in three bites, sushi was one drab California roll, and the tempura was bland and essentially free of taste. AVOID - can do much better elsewhere on the island. There are fantastic restaurants around the island - explore by all means.
LOCATION: We were very active this trip; biking down Haleakala, driving to Hana and a daytrip to Lahaina, spending time in upcountry, etc. Wailea is pretty central and is a better base for exploring than Kaanapali. Kihei isn't too lovely in spots, but has a nice selection of restaurants when you want to leave your resort, and you can bypass it when going elsewhere on the island.
FINAL WORD: what is up with the "resort fee" that just about every place is charging now? $20 extra per day for "free" local calls, coffee in room, and use of public areas. Isn't this why we are paying $500 + per night for our room? People pay this without complaint, so they keep tacking on extra charges to what used to be included in the room charge. Also, they add tips for housekeeping, valets, bell service, etc to your bill upon check-out. A mandatory per day charge is NOT a gratuity - it's just an additional charge. Plus, I'm sure many guests are unaware of this automatic addition to the bill, and tip on top of this. A VERY ANNOYING trend in the hotel business.