Just returned from spending one week at the Grand Wailea, and would gladly recommend this hotel to anyone, however my recommendation does come with warnings.
First the "good". This hotel/resort is absolutely beautiful. The grounds are well kept, the rooms are clean and spacious, and the beach is one of the best I've ever been to. Having arrived at Grand Wailea after a week on Waikiki Beach, I'd take Wailea Beach any day of the week over Waikiki. Not a single rock to be found, just nice clean sand. All of the various pools were very nice, however as we don't have kids, we tended to spend our time by the adults-only pool when not at the beach. For families, the remainder of the pools are very kid-friendly, and I'm sure they would have an absolute blast between the water slides, waterfalls, lazy river, and rope swing. For those wanting to experience a luau without leaving the hotel, the Grand Wailea does offer one right on the grounds (I'll comment more about this later). Our room was in the Chapel Wing, which was perfect for us. It was nice and quiet, as the pools were on the other side of the property, which was just far enough away, while still only being a short walk. The room was very large, with a fantastic balcony. The large bathroom was also a nice discovery. As far as the physical features of this hotel, I really cannot find fault with anything. They've done a very nice job with the design and layout. You will hear a lot of complaints from other reviewers saying it is just too large, and too far to walk to anything. In my experience they are wrong. Yes it is large, but based on seeing everyone in their bathing suits, I think most could use that little bit of extra exercise! Having driven around the island, I think Wailea Beach is one of the nicest areas too.
Next the "bad", if you want to call it that. This place is expensive! We knew that going into it, so it didn't come as a surprise, but my recommendation is to do your homework. As long as you're prepared for it, it's not bad. For example, a simple cocktail is $14.50, or $22+ if you want it in one of thos souvenier cups. Beer is $7 to $8.50 if I recall correctly. Because of this, I really didn't see a lot of people drinking excessively, which is good, although I honestly think the hotel would make more money, and the guests would enjoy more drinks, if they dropped all prices to under $10 (which is still too high in my opinion). Meal options are limited. There's the Bistro Molikini and Humuhumu..., and that's basically it. Expect to easily pay $75+ for 2 people for every single meal. There are a few other little snack bar areas, but we didn't try those. The breakfast buffet is something like $40 per person, maybe just under that. If you don't have a car to get away from the hotel for meals, that's pretty much what you can expect to pay. As others have said, there is also an arbitrary $25 per day resort fee on top of your hotel price. This one puzzles me. If I'm paying well over $400 per night to stay here, should that price not include the ability for me to swim in the hotel pools? I knew about this fee in advance, but it still irked me. I'd rather that they just put that in the price of the hotel, and not include it as a seperate charge. As far as the pools and beach go, shade is at a premium, and if you want shade, be prepared to pay for it. To rent one of those little cabana's for the day, the charge is $350 - for one day! Needless to say, I chose to stay in the sun, or on some lucky occasions, was able to get some partial cover from a palm tree. There were people paying this though, so obviously I must have been at the lower pay-scale that can actually afford this place. I was very surprised to see as many children here as we did. As I mentioned earlier, between the pool and the beach, this hotel is very kid-friendly, however at these prices, I can't believe anyone would WANT to bring kids here! That said, they didn't bother me at all, and it certainly didn't take away from my enjoyment, it was just an observation. As far as the luau was concerned, if it was the only one I say, I'd probably say it was fine. However several days earlier I had attended the Old Lahaina Luau, which is FAR superior. The Old Lahaina Luau was very traditional, and very well presented all around. The Grand Wailea luau was not traditional at all. I think once the girl swinging from the rope came out a' la' Cirque du Soleil, my mind was made up. It was a good show, but not a luau. The Hawaiian music was nice, but again, not luau music. We watched it for free from the pool area, so I don't know how much it would have cost to actually take part in it and have the dinner, but if the price is anything like the other prices around here, it's too much. Do yourself a favour and watch the show from the pathway, where your view will be just as good.
One problem you're going to have at every hotel, cruise ship, and resort in the entire world is people who get up early, throw a towel on the best poolside chairs, then leave for hours at a time. This hotel has the same problem, and although they claim there is a 1 hour policy whereby they will remove the towels if nobody shows up, they really don't start enforcing this until after 3pm. Knowing this, we didn't even try. We slept in, had our breakfast, then got whatever chairs we could find whenever we were ready to head out, and honestly, that worked just fine for us. No matter where you end up, all of the pools and the beach are readily accessible, so I think people complain too much about this. Not once did we ever have to line up for towels or the pool wristbands. I'm on vacation, the last thing I want to do is be stressed out every morning, getting up early, getting into the wristband line early, and fighting over chairs. Just wait an hour or so, and after all that craziness ends, then go down. Given that you're not likely to find shade anyway, is it really that big of a deal to wait until 8:30am instead of 7am? I found the wristbands annoying at first, but then eventually understood why they are necessary. The beach is public, and it wouldnt take much for anyone to help themselves to the amenities and pools offered by this hotel. The wristband ensures that only those who are actually staying in the hotel can use the pools. The beach however is a free-for-all, with several area hotels also using the same beach.
Overall we really enjoyed our stay here, and given that this is a premium hotel, yes it is going to be expensive. I just think that if they lowered some of their drink and meal prices a little, and got rid of the $25 daily cash grab, I'd be able to give it 5 stars instead of just 4.
Extra Tip - If you're thinking about staying here, watch the movie "Just Go With It" with Adam Sandler and Jennifer Aniston, as it shows off several areas of the hotel quite well. If you decide to stay here, it's kind of fun finding the areas where the movie was shot, and imagining the movie while you're actually standing right there.
Ask for the Chapel Wing if you want a nice view, yet some peace and quiet away from the pools.
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC