On today’s episode of spending my adult money to do things on my childhood bucket list, I checked into the Grand Wailea on Maui ; ) Ever since Samantha Brown featured the Grand Wailea on her show Great Hotels in 2002, it’s seemed like the be all, end all. 

I’ve actually spent a fair amount of time at the Grand Wailea over the years (shopping, dining, the luau, the spa, etc plus a stay years ago before my blogging days), but I was way overdue for a full blown stay. Especially since the property has undergone a top to bottom renovation over the last few years. 

I cashed in some Hilton points (you can read about my travel hacking method here) for a couple of free nights which made the cost of my three night stay a little more bearable. 

Here’s EVERYTHING you need to know about the Grand Wailea…

Grand Wailea Review

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Located in South Maui’s luxury resort area, Wailea, the Grand Wailea is the area’s flagship property and after over 30 years of hosting multi generational family trips (this is the kind of place where a couple would spend their honeymoon then bring their children back years later and now their grandchildren…decades and generations of family memories!), it’s become pretty legendary and has a fiercely loyal clientele. 

And it has a reputation for being the best luxury resort on Maui. In Hawaii! 

But is it? ; ) I will be completely honest…I have a bit of a love/hate relationship with this resort. 

Things I Love about the Grand Wailea

For starters, this is the kind of hotel that has gravitas. “Grand” really is the best way to describe it. It’s one of those places where your jaw is on the ground as you enter the lobby and walk around the property. The architecture, design, and layout is just over the top. 

It’s hard not to be impressed. 

The Grand Wailea really does feel like its own little world and if your main goal is to hole up someplace on the beach with every amenities you could want at your fingertips, you’ll love this. 

Next up, I love Wailea. This is my favorite area of Maui to stay and honestly, probably in all of Hawaii. While other places in Hawaii have resorts that I may love more than individual resorts in Wailea, Wailea has such a large concentration of high end resorts that it really is a “bubble.” 

My favorite thing is grabbing coffee in the mornings and strolling along the Wailea Beach Walk. It makes it easy to access all of the amenities of the other resorts (shopping, dining, tennis, golf, snorkeling, etc.) plus Kihei is closeby with a TON of restaurant options. And Wailea (South Maui in general) is the most convenient location for exploring the island. 

But let’s get to the main event…

The Grand Wailea’s strong point is the pool area. It’s practically its own waterpark, and it’s an absolute paradise for kids. There is just so much going on at this place. 

Aulani (the Disney resort) on Oahu is widely regarded as the best resort in Hawaii for kids, but when people ask me where to stay on another island that’s similar…this is the place. 

It’s a whole complex of pools connected by a series of slides and a lazy river. 

Notable pool features include a series of grotto caves with waterfalls (home to the Grotto Bar), a Tarzan rope swing, volleyball set up in the main pool, a sand bottom lagoon perfect for little ones, and a network of slides ranging from short little pool connectors for toddlers to some of the tallest and longest slides on Maui to a raging river rapids slide. 

The pool complex at the Grand Wailea is big and vast enough to provide hours and hours of entertainment for the kiddos. 

I also really enjoyed dinner at Humuhumunukunukuapua’a. It was completely reimagined as one part of the hotel’s renovations and it’s SUCH a dreamy spot for dinner. Obviously, it doesn’t compete with Mama’s Fish House, but it probably has the best overall ambiance of any restaurant in Wailea. 

And we had a really nice meal at Olivine.

Other things I love about the Grand Wailea…it has a prime spot on Wailea Beach which is usually fairly calm and swimmable. 

And the resort has a lot of on property shopping (Bikini Bird is my favorite!)

Also, the adults only pool has food and drink service from Olivine, one of the resort’s brand new restaurants, which I thought was above average in terms of what’s usually offered at resorts like this. 

The completely overhauled Kilolani Spa is FABULOUS. The facilities are definitely the best on Maui (by a long shot).

***Want to save major $$$ on your trip to Hawaii? I get asked ALL the time how I’m able to travel so often to Hawaii and stay at really nice resorts. Well, my favorite travel hack is cashing in points to score free airfare and free nights at some of Hawaii’s most high end resorts. Read my full guide on the exact system I use to max out credit card rewards here. Seriously, it’s going to save you soooo much money. 

Things that Could Be Better

My major point of complaint with the Grand Wailea (from many, many visits to dine and shop here plus a previous stay) was solidified on this trip. 

The service is hit or miss, usually pretty lackluster, and for a place this size that serves the luxury market, they should have about 10 times as many employees working here. 

I checked in fairly early in the morning, but it’s not uncommon to hear about hour-long waits to check in mid afternoon due to a lack of staff. 

This is a BIG hotel with a lot of guests, so expect to encounter lines (for beach chairs in the morning, at the shack to get wristbands, at the coffee shop, at the valet, etc.) and just generally not enough employees. 

They don’t have staff to monitor pool chair use so it can be hard to get chairs midday and there was often trash in and around the Grotto Pool Bar because people leave their cups at the tables in the middle of the pool and there’s no one to go around and pick them up. 

To be clear – this is not an employee work ethic problem. It’s a problem with management and ownership cutting jobs and hours. This seems unacceptable when prices push $1200/night. 

Other things that are in the “con” category:

The rooms are fairly lackluster. They have all been completely renovated recently and they’re clean and fine, but again, at $1200/night I expect more. 

The aforementioned Grotto Bar is actually in one of the more heavily trafficked kids pools, which is…weird. 

The resort’s famous water elevator (the novelty feature that whisks guests up to the tallest slide) hasn’t been operational in over four years (but when guests ask about it they act like it just happens to be closed for the moment ; ) 

Now let’s talk about…the adults only pool. I think it’s one of the weakest set ups in Wailea. It has an outdated design where the pool and all of the chairs and cabanas are oriented where you’re looking back at the resort buildings instead of…the ocean…which is right behind it. 

The one set of 6 or so chairs that are set up facing the ocean are mostly boxed in with a hedge which seems…unnecessary. 

And lastly…I don’t ever expect a bargain in Wailea, but I think the prices around the resort (especially at Loulu – the quick service/breakfast/coffee shop) are pretty excessive. They just partnered with Erewhon (the over the top priced LA grocery store chain) and $15 protein bars and $20 smoothies are just not something I’m ever in the market for. 

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Overall

I LOVE a big, comfy resort with a lot going on and the Grand Wailea delivers on a lot of that. This is the kind of place where you feel like you could spend whole days never leaving the resort. 

I don’t love when a resort that’s priced and positioned as a luxury resort underdelivers. Especially in a location with competition is FIERCE. Just a stone’s throw from the Grand Wailea are some of Hawaii’s best beach resorts. 

And while the Grand Wailea definitely serves a certain market, I wouldn’t put it on a list of top luxury resorts in Hawaii. 

It’s a kids’ hotel. 

Which is AMAZING if you have kids. But if you’re not traveling with kids, I don’t think the Grand Wailea is a top contender for the best hotel in Wailea. 

If you want actual luxury, the Four Seasons and Andaz are both better choices. And honestly, I’d take the Wailea Beach Resort and Fairmont Kea Lani over the Grand Wailea. Their more manageable size (the Grand Wailea is honestly a little TOO big to be convenient), better customer service, and more reasonable price is pretty attractive. 

Now don’t get me wrong, the Grand Wailea gets plenty right, but unfortunately (or fortunately for you), you don’t actually have to stay at the Grand Wailea to visit the spa, shop, dine at Humuhumu, or walk around the grounds. 

So bottom line…if you have kids and you want the ultimate pool and beach experience, this is the place to be.

If you don’t have kids, I think it’s the place to avoid ; ) 

You can book the Grand Wailea here.  

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