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Grand Wailea Review: A Waldorf Astoria Resort

The Grand Wailea has been an anchor resort in the post Wailea resort development since opening in 1991. Its massive wings of resort rooms towers over one of the most impressive pool complexes on earth, complete with its own water elevator (when in operation). Opened as a Hyatt, it's now a part of the Waldorf Astoria brand, making it a popular option for redeeming Hilton points (if you can find availability). With two visits under my belt, and some perspective on other places to stay in Maui, here's my Grand Wailea, A Waldorf Astoria Resort review.

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The first thing to tackle in this Grand Wailea review is the location. The property is located in Wailea, Maui, about 16 miles from Maui's Kahului Airport (OGG). Many guests rent cars on the island because there's so much to explore off the resort, but note that the hotel does charge $65 per day for parking (valet only). Sadly, Hilton doesn't offer a waived parking benefit for award stays like my beloved Hyatt. With those prices, I might consider taking a shuttle to the resort from the airport, and renting a car for the day from the hotel.

The town/development of Wailea has several luxury resorts nearby, including an Andaz, Fairmont, and Four Seasons. There's a great walking path on the oceanside of the resorts connecting all of them together, so it's an easy walk off property for dinner or exploring.

Pro Tip:

The happy hour at Tommy Bahama's at the Shops at Wailea next door to the resort is a great deal for the island. They also have and ABC store and general store for anything you may need, could have forgotten.

Grand Wailea Review

Typical Hilton Honors Booking Cost

The Grand Wailea is a Hilton Honors property, meaning it will cost you 110,000 Hilton Honors points for a standard level room (if you can find availability). Hilton properties currently top out at 120,000 points a night, so this is one of the more expensive redemptions in their portfolio. Keep in mind that Hilton does have a 5th night free on award reservations, and that's how I booked my stay. I added an additional night with a free night certificate from my Hilton Aspire card.

Hilton is a transfer partner of American Express Membership Rewards, but is typically not a great use of those points. Hilton also recently partnered with Bilt as a transfer partner as well.

A base-level room with a garden view typically starts around $800 per night, plus a $50 resort fee (waived for those staying on an award reservation). That is pretty steep for a property with 787 rooms. Rates have increased significantly in recent years, no doubt due to the popularity of the islands exploding after re-opening.

Pro Tip:

If you manage to score a points award, keep in mind that it's for a base-level garden view room. Personally, flying all the way to Hawaii and having a non-ocean view is a bummer. Because of that I suggest reaching out to the property before your stay to review paid upgrade options if that's important to you. I received a free upgrade to a partial ocean view for my stay due to my Diamond status, but not after some “intense” negotiations with the front desk!

Grand Wailea Review

Check In

When you enter the Grand Wailea, A Waldorf Astoria Resort property, it takes your breath away a bit. You see open air hallways everywhere, a stunning floating center bar area and may even get a view of the ocean in the distance. The check in area, on the other hand, is a bit uninspired. During our stay they had just a few agents working the desk, which was surprising for a property of this size. Luckily, we weren't hit with too long of lines and the representatives were very helpful. You should get a very nice Hawaiian lei at check in if they still have some on hand.

We were offered an upgrade to a an ocean front room, which included lounge access, but at over $300 a night we decided to stick with our partial ocean view complimentary upgrade.

Pro Tip:

This property is “tiered,” as the lobby is several floors above the pool and beach area. Learn where the elevators are quickly to navigate the property more efficiently!

Room Review

Coming to this resort I expected the rooms to be showing their age. To be honest, I figured it would be a big talking point in our Grand Wailea review. I have to admit that I was pleasantly surprised with what I saw. Maybe it was because I had low expectations, but the rooms had modern colors and the furniture and bathroom were in good form. The hallways and tile around the property have seen better days for sure. They are due for a major renovation of the public areas of the resort. Especially with the prices they are charging most of the folks staying there. Who knows when, or if, that will happen though.

Grand Wailea Review

The room was of standard size and set up. I did find the bathroom to be very spacious , and it was my second favorite part of the room. My favorite part was, of course, the balcony. With stunning views of the beautiful gardens on property, and the ocean as a serene backdrop, we spent a fair amount of time out there.

They even had a drying rack for our swimwear, but we figured out that this worked better setting it up inside in the tub. Nothing seemed to fully dry out when set up outdoors.

Pro Tip:

Other Mark here. When we stayed on property a month ago we had a double bed room for the four of us. We decided to stop by Target after landing and bought a $15 twin blow up mattress. We brought a small air pump, and some old kids sheets that we were ready to throw away with us. Each night, we had one child sleep on the blow up mattress so we had a bit more space for everyone. We used it throughout the rest of our trip too. It made the entire vacation a lot more pleasant, and didn't cost us much to pull off with a little bit of planning.

Grand Wailea Review

Grand Wailea Resort Review: Property Amenities and Activities

Where the Grand Wailea excels is in its pool area. When I was first researching the property, I couldn't really understand how it had a “water elevator,” but was excited to try it out. Essentially, the pool area is built on a hill-like complex. If you start at the top level pool, you can continue downhill on wide slide-like connectors that drop you to the lower level. At the bottom level, there are lazy river sections that continue to the main pool, the grottos, and the water elevator. The water elevator operates every couple of minutes, and floats you back up to the top level of the pool, all without you leaving the pool itself. It's pretty great. Unfortunately, it is often closed for repairs.

Grand Wailea Review

As mentioned, the Grand Wailea has the Wailea Canyon Activity pool, which is really 9 pools on 6 different levels. There are many slides interspersed between the different pools themselves in this area, but the largest traditional slide is the Lava Tube slide. Inside all of this are several grotto-like areas with waterfalls and a hidden bar, which was my favorite part of the whole resort. The slides are open from 10AM until 5PM, and that is one of the negatives of this set up we should bring up as well. When these are not running it is noticeable, and makes the pools a lot less enticing all split up. Because of that, you will want to take advantage of them as much as you can while they are running!

There's even a Tarzan rope swing for daredevils. Finally, for those looking to try out scuba diving, there's a specially-designed dive pool that offers free scuba experiences, in hopes you want to try out scuba in the ocean during your stay.

Beyond the Canyon Activity Pool, there is also the Hibiscus Pool (pictured above), which is adults-only. This is where you'll find cabanas for rent, and a more relaxed feel. There's of course bar service and loungers spread throughout the large (and surprisingly deep) pool.


The Grand Wailea is of course located on the ocean, which can sometimes take a backseat to the fun of the pool area. Located across the public walking path from the resort is the main beach area, which is set up with many of the resort's beach chairs. You can take snorkel and outrigger tours from this beach for an extra fee. I found the snorkeling to be excellent around the Wailea resorts, due to the rocky outcroppings that fish seem to love.

Grand Wailea Review
Sports and Leisure

One of the negatives of our Grand Wailea review is that despite the massive size of this resort, there aren't many sport activities on property. As mentioned, you can try your hand at Scuba in the scuba pool, snorkeling and swimming off Wailea Beach. However, there are no tennis/pickleball courts or golf courses on property. To use those, you'll have to travel up the hill away from the resort to Wailea Tennis Club and Wailea Golf Club, which are public access. There are 9 tennis courts and 10 pickleball courts, and 3 18-hole golf courses to choose from, which is great. I just wish it was more convenient to access for resort guests.


The resort's gym is very expansive, located near the resort's spa facilities. This is necessary due to the resort's size– you'd be surprised how many mega resorts don't have an adequately sized gym! The gym stayed busy during each of my visits on property, so visit in the afternoons to avoid the morning rush.


The spa is located downstairs, and it is a very beautiful and welcoming place. We went down there just to purchase some Hilton gift cards to use up our quarterly credits. We did not partake in any services so we can not comment on that.

Grand Wailea Resort: Dining

The resort has many dining options on property, in addition to all the dining options available at other resorts nearby. If you're reading this review, you might be looking for ways to maximize your Hilton Aspire $200 bi-yearly credit. That credit will work on property, but with how high prices are at the Grand Wailea, it's not going to go very far!

Expensive Dining

Probably the most famous restaurant at the Grand Wailea is Humuhumunukunukuāpuaʻa (it's the state fish). This restaurant has excellent ocean views and an aquarium bar that's really unique.

Olivine is a new oceanfront restaurant on property that's open for dinner, but other food options include the Botero Lounge, Loulu, and the Grotto Bar. The Wailea Surf Haus is a beach bar that serves up cocktails and beers for ocean-goers. Breakfast is served at ‘Ikena, which is on a terrace near the main lobby and it can be very pricey for a buffet.

Pro Tip

If you want to use your Hilton dining credits on breakfast then Loulu will be your best option. This is kind of like a grab and go restaurant with a market attached. You can get bagels, sandwiches and smoothies here. For a family of four or more, the credits likely won't cover the full cost. But, you at least won't have to remortgage the house to pay for the breakfast buffet. The best option may be grabbing granola bars etc. from the store for breakfast and then using your credits for lunch at the pool etc.

Grand Wailea Review

Off Site Dining Options

My favorite options for food and drink at the Grand Wailea are located off the resort. The Shops at Wailea have many dining options, my favorite being Tommy Bahama's for their aforementioned happy hour. Up the hill, but still a part of the Wailea development, is a small shopping center with some more local options. The most popular restaurant here is Monkeypod (wings pictured above), which has a great menu featuring local fish and unbelievable pizzas. Don't miss their mai tais with the passion fruit foam!

Other resorts in the area have options, too. Morimoto has a restaurant at the Andaz, a short walk away, and if you're looking for fine dining, Spago is located at the Four Seasons to the south of the resort.

Pro Tip:

There's a grocery store at the Shops at Wailea where you can load up on necessities that aren't resort priced. It's also a cheaper option for that morning coffee.

Resort Service

Overall, I think the Grand Wailea service quality suffers from its size. There are some great employees of the resort that deliver individually great service, but when something goes wrong, it can often take some work to get issues resolved. My first stay on property had several issues (rude valets, no towels in our room, and moldy blueberries at breakfast), and the management of the property was very difficult to work with. I did get my issues resolved, but it left a bad taste in my mouth from the experience. I had wished the property was more understanding of my concerns. A property that charges this much for a night stay should be held to a higher standard.

Grand Wailea Review: ToP Thoughts

The Grand Wailea is a dream resort redemption for many Hilton loyalists, and I understand the appeal. If you have smaller children, and are looking for an amazing pool experience, then this is a great option for you. I just wouldn't expect the 5 star attention and service that may be expected at this price point and with the Waldorf Astoria name. You will also want to raid the Costco by the airport before arriving to save on food costs where you can.

For myself, having visited the property several times now, I have to say that the pricing for rooms, food and beverage at the resort, and the resort's overall size, detracts from my vacation each time I visit. With so many other options on Maui at a similar price point, I'd look elsewhere if I wasn't aiming to use my Hilton Honors points for a redemption.


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