The Grand Wailea Maui is an extremely popular hotel by Hilton, and it is the largest on the entire island of Maui. I’m going to be as balanced as possible in my Grand Wailea Maui review, but I must be honest that I was really looking forward to this hotel, and it didn’t live up to my expectations. I hope that my experience was not the norm! Regardless, I’ll tell you how to stay there for free too.
And while you’re in Maui, I made a list of the best, locals-only, secret Maui things to do here. Check them out while you’re on the island!
Overall: Beautiful, luxury resort property that lacks some of the basics.
Pros: Great location, amazing pools, good use of Hilton certificates and points.
Cons: Really terrible check-in and service experience for a night.
We paid: 95,000 Hilton points and $306 for a 2-night, $1,112 stay.
How to stay at the Grand Wailea Maui for less
- Get one of the Hilton Amex cards and link it to your Hilton account.
- Hit the minimum spend required for the Hilton card you chose:
- $4K for the Hilton Amex Aspire card (which is my favorite) – See why here!
- $3K for the Hilton Honors Business card
- $3K for the Hilton Amex Surpass card
- $1K for the Hilton Honors card, which is fee-free
- Wait for your bonus points (and/or weekend nights) to come into your Hilton account.
- Once your bonus points/nights hit your Hilton account, search the app or website for award availability. Standard nights at Grand Wailea Maui typically run 95,000 points per night. You can stack free weekend nights with a night you book with your points too.
- The Grand Wailea Maui is an official Hilton Resort property, and thus eligible for a once-yearly $250 rebate on room rates or anything at the hotel, if you have the Hilton Aspire card and use it for these purposes. We paid for one of our room nights with the Hilton Aspire card for that reason.
- Book online through the Hilton app or website, OR if you want to stack your weekend night(s) to the reservation, you should call Hilton.
- Make sure to take advantage of your elite benefits during your stay, which include an awesome Executive Lounge if you’re a Diamond!
For full instructions, see my guide to booking Hilton hotels for free.
Location: Grand Wailea Maui Review
The Grand Wailea Maui is well-located on the Southwestern coast of the island by Makena Beach. Hawaii’s islands are very weather-affected, meaning some coasts are only good for visiting the beach and snorkeling during the summer months. Not true for this hotel. The Grand Wailea Waldorf Astoria Maui is ideally-located for all water activities, year-round. It’s situated directly on the water, above a beautiful stretch of fine white sand.
This hotel is a large resort in its own right, with plenty of on-site restaurants. However, it’s also about a 15-minute walk to the lovely Monkeypod Kitchen by Merriman. We enjoyed the neighborhood as we walked.
One downside to the location is that the property forces you to use their $40/day valet service. We had rented a car from the airport, about a half-hour’s drive away. Unless you want to try to find free parking by walking around the island, you’re kinda stuck with it.
Unfortunately, this forced-valet service can be incredibly slow. They took over 20 minutes to retrieve our car when we were trying to head out to the airport! It was pretty ridiculous.
But aside from that, the location of the Grand Wailea Maui is awesome. You can walk to the Andaz Maui, the Four Seasons, or any number of nearby restaurants, and you’re at the best beach on the island.
Terrible check-in experience: They failed to check us in, so we had Security banging on our door in the middle of the night.
This was a basic issue that the hotel really failed us on. But before I get into it, I said I wanted to be balanced in my Grand Wailea Maui review, and to be fair, they did apologize for and rectify the issue. Ok, so here’s what happened:
My partner and I booked a two-night stay with two separate reservations, one with points and one with cash. Although I had called ahead to link the two reservations together, this hadn’t happened properly. No problem, but the desk attendant was very confused by the process. I had both confirmation numbers handy, so after 30 whole minutes, they eventually sorted it out.
Or so I thought.
They gave us a two-queen-bed room when we had booked a King bed, and the hotel wasn’t full. No upgrades despite Hilton Diamond status. I wasn’t very happy and left a message on Hilton’s app stating that I didn’t get the room I booked.
Oh well. I forgot about the issue and went to enjoy Maui. I didn’t receive a response from anyone at Hilton. We went to bed for the night.
Then the REAL trouble started.
A man pounded on our door a little before midnight. It woke me and my partner out of a sound sleep, but we figured he had the wrong room. Ten minutes later, we got a call on the room phone stating that security was outside our room “responding to a lockout request.” I said, “you have the wrong room, leave us alone.” At 12:07a, we got another call from the front desk demanding to know who we were and telling us to GET OUT! We hung up and called the front desk back because we thought someone was scamming us or even trying to rob us. Turns out, staff had failed to check us into ANY room. We were marked as no-shows for the night.
So the hotel staff took 30 minutes at check-in and didn’t even manage to check us in. (Why did our keys work? I have no idea.) When they woke us up in the middle of the night, they had no record of us, so we had to chase down our confirmation numbers yet again. Needless to say, this ruined our night.
Mitigation of terrible check-in experience: One night free
This was a critical failure at so many different points: The check-in didn’t occur. No one responded to my complaint about getting the wrong room. Security didn’t try to figure out what was going on before scaring the crap out of us multiple times. While we were on the phone with the front desk in the middle of the night, they accused us of breaking in. So many things went wrong, and no one even tried to proactively fix the issue – or even apologize to us!
I was seriously pissed about the whole thing, and genuinely surprised that a manager didn’t try to reach out. So the next morning, we took the step of contacting the hotel’s general manager to complain. I’ll give credit where credit is due: The Waldorf Astoria Maui really came through with an apology. They admitted I got the wrong room, as I had said in my (ignored) message. I should’ve had an upgraded King room. It took them until 4:00p the next day, but they moved us to a King room with an Ocean View for our second night, plus a nice display with a personal note.
Not only that, but they refunded our entire first night’s stay. I really appreciated that. It had ruined our night, and I don’t think I would’ve felt good paying the $556 sticker price for that, so this was a good mitigation. For the purposes of this Grand Wailea Maui review, I would’ve paid $306 – the full $556, less the $250 resort fee from the Amex Hilton Aspire card. But since they didn’t charge me for any of it, I actually paid $0 for the first night.
I paid for my second night with 95K Hilton points instead of cash, and we had a much better second night at this resort! Which brings me to…
Our room at the Grand Wailea Maui
Once we got the appropriate King bed room with a lovely ocean view, we were much happier.
As you can see, the view from this top-floor room is wonderful. We really enjoyed drinking our champagne from the generous balcony.
The room was also quite spacious, with ample space for a King bed and a couch.
Our bathroom was white and marble, with a separate soaking tub and stand-up shower. We loved the fluffy robes too.
The minibar allowed us to keep our own beers cold, which was nice.
And, this hotel provided a lovely turndown service with high-end chocolates too:
Once we got the correct room, I was much happier about this resort.
Pool and amenities at the Grand Wailea Maui
The pool is just phenomenal. I didn’t take my own pics, so you’ll have to take my word for it or check out the hotel’s gallery here.
The Grand Wailea Maui doesn’t just have “a pool,” it’s more a “luxury water park.”
Each pool has a nearby dining area and poolside service for cocktails. We really enjoyed ordering cocktails and then hanging out in the lazy river. There’s an adults-only pool and hot tub area, which is nice for those who want to escape the multi-family resort vibe.
We didn’t experience the other amenities, which are supposed to justify the $30 nightly resort fee. There is daily entertainment and some complimentary yoga and meditation sessions.
The Grand Wailea Maui is a luxury RESORT, emphasis on resort. As a resort property, it’s very large and, well, resort-y. It takes a while to walk around, and there are lots of excellent but high-priced bars and restaurants and shops everywhere. On-property, you’ve got amazing pools and activities. Immediately off-property is a super nice beach with clear water. If you want to park yourself in one place for a few days, this is where you’d do it.
My partner and I had a very nice second night!
Overall impression
It’s hard for me to provide an “overall impression” because I had such a terrible first night, but then a very nice second day. I’ve tried to be as balanced as possible in my Grand Wailea Maui review, and I hope you agree.
My true overall impression is that this is an enormous resort property, and some things slip through the cracks. Resorts are big, and they move slowly, and they employ lots and lots of staff that are hard to train and keep track of. Thousands of guests are staying there at a given point (aside from COVID-19, I mean). All of these things make resorts difficult to run. If you happen to have some bad luck with a poorly-trained front desk agent, getting the wrong room means you’re likely to get lost in the shuffle just like I did.
Truth be told, I’m not really a “resort person,” so you should take that into account when you’re deciding for yourself whether to stay at the Grand Wailea Maui. I enjoy personalized service at luxury hotels, rather than massive resorts. I like leaving my hotel to explore the local area. But by design, resorts are these insulated oases that don’t make it easy to leave. (Recall the $40 forced-valet service that takes 20 minutes to retrieve your car.) That’s just how resorts are, and the Grand Wailea Maui is no different.
But the good thing about resort properties is that there’s a ton of stuff to do on the premises, and the Grand Wailea Maui provides some of the best activities. If you ARE a resort person, you could spend many days here without wanting to leave the property.
Bottom line
I hope I provided a balanced viewpoint in my Grand Wailea Maui review. On the one hand, it is truly a beautiful property with so many things to do. The beach, the pools, and some great restaurants are all on the resort, so you can spend days here and not be bored. If one person hadn’t made a big mistake at check-in, I probably would’ve had a very different experience! On the other hand, there were multiple points of failure after the first mistake, and I was disappointed it took until 4:00p the next day to get our room switched.
Would I go back? I don’t know. I’m actually tempted to give the Grand Wailea Maui another try, because maybe they were just having a couple of bad days, and I really did like the property. I’m also sitting on a lot of Hilton points right now. Maybe when Hawaii opens up again, I’ll think about it!
