We just got back from a week at the Grand Wailea, and I have a lot of thoughts. We'd been hearing about this resort for years - the resort to visit in Maui, famous for its absolutely legendary pool complex - so expectations were high. Were they met? Here's the full rundown on everything from the rooms to the restaurants to the beach, and yes, that pool.
The Property & Location
The Grand Wailea is located in Wailea, on Maui's sunny south shore. This is Maui's premier resort area - a stretch of upscale hotels, gorgeous beaches, and top-notch restaurants clustered along the coastline.
Wailea tends to be drier and sunnier than other parts of the island, which is a huge bonus if you're coming to spend time at the beach. The resort sits right on Wailea Beach, with easy access to the Wailea Beach Path, which connects all of the resorts on this little stretch of coastline.
The Grand Wailea itself is a massive, sprawling property - over 40 tropical acres with around 780 guest rooms and suites. It opened in 1991 and has been one of Maui's most iconic resorts ever since. It's a Waldorf Astoria property these days, although I'm not sure the level of "fanciness" quite lives up to the Waldorf name on this one.
I should emphasize here that this resort is big. Really big. If you're in one wing and need to get to the other side of the property, you're in for a bit of a hike. (It's a lot like Atlantis in this way.) So bring your walking shoes!
Getting to the Resort
You'll fly into Kahului Airport (OGG), which is Maui's main airport. The Grand Wailea is about 17 miles from there - roughly a 30-minute drive under normal conditions.
Unlike some international resort destinations, you don't need to pre-arrange transportation here. Taxis are always available at the airport, and most of the resort areas in Wailea are reachable in under an hour, so there's no stress if you haven't booked anything in advance. Rideshares, like Uber, work here too.
That said, if you're planning to do any serious exploring - beaches beyond Wailea, the famous Road to Hana, or restaurants and shops away from the resort strip - a rental car is highly recommended. You can pick one up right at the airport, or you can use the Enterprise location right inside the hotel. Maui rewards the people who venture out of the resort bubble, and you'll want the flexibility to do that on your own schedule.
Our Room - Ocean View Double
We booked an Ocean View room with two double beds, which worked perfectly for our family. The room was very spacious - all Grand Wailea rooms start at 640 square feet, and you feel every bit of it. We had plenty of room to spread out, which I always appreciate after a few days living out of suitcases.
The oceanview balcony (lānai) was one of our favorite features. The views across the resort pools and out to the Pacific were really beautiful. We even spotted a whale from our balcony one morning, which was a pretty magical way to start the day! The balcony had chairs and a small table, and we used it every single morning for coffee and breakfast.
The bathroom was very large and well-appointed. There was a large walk-in shower, a separate soaking tub, a water closet for the toilet, and a sink with plenty of counterspace. (Although, no double sinks.)
Toiletries were good quality and actually usable. I know you guys like to have all the details for your trip planning, so here are some pics of what was offered by the sink and in the shower. There was a real hair dryer too, not one of those wall-mounted contraptions. You all know how I feel about those hotel hair dryers by now. ;)
Storage space was also excellent! There was a big closet with a safe (large enough for a small laptop), plus plenty of drawer space in the dressers. We had no trouble fitting all of our beach gear, luggage, and clothes without things feeling too chaotic.
The room came with a mini fridge and a coffee maker, which we used every day. There is no microwave though, which would have been a nice touch.
A couple of small complaints though. The mattresses were quite bouncy - not what I'd really call comfortable. Enough that my husband complained about it every morning. This is subjective, of course, but worth noting.
Also, there was only one USB charging spot on the nightstand, which feels sparse for a luxury resort in this day and age. Come prepared with a travel charger with multiple ports!
Other Room Types
The standard rooms all start at 640 square feet with a private balcony or patio- larger than most hotel rooms you'll encounter anywhere. You can choose your view: Garden View rooms overlook the lush tropical grounds, Ocean View rooms offer partial ocean views (like what you see in my photos above), and Deluxe Ocean View rooms on the upper floors give you the full panoramic treatment. If you're on the south-facing Molokini wing, the Terrace View rooms look out toward Mount Haleakalā - a different kind of beautiful.
The entry-level Lagoon Ground Floor rooms are the most budget-friendly option, located steps from the pool on the ground level. These are super convenient for pool days, though you'll sacrifice the view.
If you want more space, the resort has a whole range of suites ranging from around 1,280 to nearly 2,000 square feet, including the Honuaʻula Suite, the Aliʻi Suite, and several Wailea and Molokini Suites, all of which add a separate living area. For the ultimate in-room experience, the Napua Grand Suite clocks in at 5,500 square feet with panoramic ocean views - I have no idea what that costs, and I'm honestly not sure I want to know.
Speaking of Napua - it's the resort's exclusive club-level tier, occupying gated upper floors of the property. Napua rooms and suites run slightly larger than the standard rooms and come with premium amenities and access to a private lounge. Worth looking into if you want a notch up from the standard experience. (Tip: If they are not booked, you can sometimes score an upgrade at a reasonable rate on arrival!)
For larger families or groups, the Hoʻolei Villas are three-bedroom standalone villas ranging from 3,400 to 4,000 square feet, sleeping up to 8 guests. They have full kitchens and their own private pool access. Basically a house in paradise.
The Pool Scene
The pool is the main event here, and it absolutely lives up to the hype! In fact, I would rate this as one of my all-time top three hotel pools.
The Wailea Canyon Activity Pool is not just a hotel pool - it's a pool complex, and it is genuinely unlike anything I've seen outside of Atlantis in the Bahamas.
We're talking multiple pools connected across different levels, with water slides running down between them, rope swings, grottos, waterfalls, a lazy river, and more. It's impressive in a way that photos don't fully capture. (Although I did try!)
The star of the show (for the adults) is the Grotto Bar. You swim through a cave-like opening in the rocks, and suddenly you're inside a bar. An actual bar, with barstools, drinks, and bartenders - all while you're still in the water. It's a fun spin on a regular old swim-up bar.
The slides and water features open at 10:30 AM and run until 5:00 PM. The pools themselves open at 7:00 AM and stay open until 10:00 PM, so you can swim in the morning before the crowds arrive, or take a quiet evening dip after dinner.
There's a sandy-bottom area of the pool that's perfect for younger kids because of the zero entry. At the far end of the activity pool, there's also a volleyball net for some friendly competition.
The Serenity Pool is separated from the main pool area, and is marketed as adults-only on the website. But the signage on-site actually just calls it a "quiet pool," and we did see older kids in there from time to time. Your mileage may vary on how enforced that actually is.
One big thing to know: if you want pool chairs, you need to be strategic about it. We went down at 7:30 AM and the pool area was essentially empty. By 9:30, almost every chair was claimed each day. The chair-saving culture is fully alive here. The hotel is supposed to enforce a one-hour limit on unoccupied chairs - but in practice, that's loosely enforced. I find the whole chairs-at-dawn game very annoying. But when in Hawaii... do what you gotta do.
Wailea Beach
The Grand Wailea sits on Wailea Beach, which is truly beautiful - soft sand, beautiful views, classic Hawaii. But I'll be straight with you about the water- it's rough. It's not the greatest beach for casual swimming or for young kids. There are no calm lagoons here like at some of the Caribbean all-inclusives (like the Hard Rock!).
For older kids and adults, it can be really fun to jump waves in the shallows or even boogie board - but you do need to pay attention. On our visit, we had arrived shortly after a Kona low storm that had just passed through, and there was still a water advisory in effect when we arrived. The storm caused significant beach erosion, and all of the beach chair setups were completely absent for our entire stay. Not ideal, but obviously a bit of a fluke situation.
Beach Chair Rentals
In normal conditions, beach chairs are available from the resort - but they are not free! The charge is $150 for two beach chairs for the day. I think this is a bit insane, honestly. It may actually be the most egregious price gouging I've experienced at a resort like this. And I have been to a lot of them.
The resort does have a small number of folding beach chairs available to check out at no charge. You can ask at the pool desk to see if any are available. But the supply is very limited. I'll just say this: for a resort in this price range, charging $150 for two beach chairs feels cheap. Very cheap. It's a complaint I've seen echoed by plenty of other guests, and it's warranted.
Cabana Rentals
If you want a cabana, budget accordingly. During our visit, prices ranged from $1,000 to $1,500 for a four-person cabana, depending on location and the day. There were also super cabanas available for larger groups, and two-person casabellas (a clamshell-style enclosure) for couples who want some shade and privacy without committing to a full cabana setup.
I'm planning a separate article with all the details, tips on the best cabana locations, and what's worth the splurge vs. what to skip - so stay tuned for that!
The Wristband Situation
This is one of those things nobody warns you about ahead of time, so let me save you some hassle.
The Grand Wailea requires guests to wear a wristband to access the pools and other resort amenities - basically proof that you're an actual guest and not someone who wandered in to use the amenities for free.
When you check in, you'll receive a wristband for each adult in your group. And I'll give them credit here: these are actually really nice silicone bands that snap on and off easily. I have a deep, personal hatred of wristbands I can't remove to shower, so this detail is not lost on me.
Now - here's where it gets a little more complicated if you're traveling with kids. Children do not receive a wristband at check-in. They do, however, need one to access the pool and water slides.
On your first day, you'll need to head to the pool reception desk (the same spot where they hand out towels) and request a band for your child. Kids get a nightclub-style paper wristband - the kind you have to rip or cut off. And here's the important part: if your child is 48" or taller, they'll receive a different color band indicating they're cleared to ride the biggest water slides.
Your child will keep this band for the duration of your trip. On longer stays, be aware that the resort periodically rotates the band colors (presumably to prevent non-guests from reusing old ones), so you may need to swap it out. If you want to temporarily remove the band - say, for a fancy dinner or a bath - save it carefully and bring it back to the desk to trade in for a new one. If you lose it, they will charge you for a replacement. Consider yourself warned.
One more practical tip: the line at the pool desk can get very long right when the pool opens each day. Go early, beat the rush, and get your bands sorted before the crowds descend. Knock this out first thing on Day 1 so you're not standing in a 30-minute line when you could be in the water.
Food & Restaurants
This is where things get a little... expensive. The Grand Wailea is not an all-inclusive resort, so every meal and drink is a separate charge. And prices in are genuinely eye-watering. Prepare yourself. Here's a quick look at the on-site dining options.
Loulu's
This is a quick-service café, and it'll probably become your go-to spot for daily grab-and-go needs. They serve pizza and poke bowls, plus a selection of sandwiches, snacks, coffees, and grab-and-go drinks. There's also ice cream!
It's honestly very convenient for a quick breakfast or a snack when you don't want to make a whole event of a meal. If you're in the Molokini wing like we were, it's very close to the rooms as well. That being said - I paid $15 for two single-serve bags of chips here. So... yeah.
Wailea Surf Haus
This is the pool restaurant, and the most convenient spot to get lunch during a pool or beach day. There are a small number of tables with table service, or you can order at your beach chairs with one of the servers, or you can walk up and order food for take-out. (Walking up is fastest!)
The menu is solid: salads, sandwiches, wraps, plus kid-friendly options like chicken fingers. I had the poke nachos twice because they were excellent.
Haleakalā Shave Ice
This shaved ice truck can be found near the upper activity pools. And of course, Hawaii is famous for their shaved ice. Now is this the best shaved ice in Hawaii? I really have no idea. But my son sure loved it and wanted to get one every day! ;)
Humuhumunukunukuāpuaʻa
Let's get the pronunciation out of the way first: hoo-moo-hoo-moo-noo-koo-noo-koo-ah-poo-ah-ah. It's the name of Hawaii's state fish (the reef triggerfish), and yes, it's fun to learn to say.
The restaurant itself is beautiful - an open-air beachfront setting surrounded by lagoons, with great sunset views. If you're going to splurge on one dinner at the resort, the atmosphere here earns it.
The food? Decent, but not quite as exceptional as the setting and price tag would have you expect. I had the snapper ($80) - fresh and nicely prepared, but honestly I've had better at home in Florida for a fraction of the price. The ahi tuna appetizer was okay, the mashed potatoes were great, the broccolini was over-sauced and not worth finishing. The kids' steak was just okay. On the bright side, the coconut porter was tasty, and the pineapple cake dessert was both pretty and delicious. My take? Go for the sunset view and the cocktails, but lower your food expectations.
Olivine
An oceanfront Italian restaurant with handmade pastas and local Hawaiian ingredients. The setting is lovely for a dinner out. We did not eat a full meal here, but stopped in for drinks a few times and it's very pretty and inviting inside. It's also adjacent to the Serenity pool, so this could be a nice option for a sit-down lunch as well.
Nobu Grand Wailea
The big splurge option. Nobu is a globally recognized restaurant, and this location is beautiful, with panoramic ocean views. Their famous dishes include the black cod with miso and yellowtail jalapeño. Spendy, but you know what you're getting with Nobu. We skipped it though, as the kids were just not interested. And I should also note that the reviews are not on par with its Vegas counterpart.
The Grand Lūʻau at Grand Wailea
I guess this isn't quite a restaurant, but they do feed you dinner. The Grand Luau is the resort's own Hawaiian luau experience, featuring traditional ceremonies, music, hula, and dishes like kālua pig, poi, poke, and haupia. It's a classic Hawaiian experience. It's also a complete tourist trap. But hey, you're a tourist. So go ahead and do it once if you have time.
Nearby (Off-Resort) Options
It's worth heading off property for a meal or two. A short walk or quick drive to the Wailea Gateway Center puts you at two spots we really liked:
Lineage - Chef Emmanuel Eng's Asian-American restaurant leans into Maui's multicultural food heritage, with dishes built around local ingredients and family-style cooking. The vibe is intimate rather than flashy ("eat, drink, talk story" is basically the restaurant's whole philosophy), and it's picked up multiple local dining awards. A nice change of pace from resort dining rooms.
Monkeypod Kitchen by Merriman - A livelier, more casual pick, known for kiawe-wood-fired pizzas (the kalua pork version is a favorite), fresh local seafood, and a serious cocktail and craft beer program - 36 taps, plus nightly live music. Great if you want energy over romance for a night.
Both are easy to combine with a stop at the Shops at Wailea if you want to make a full evening of it.
The Cave
Tucked away on property is a newer addition called The Cave. It's branded (a little dramatically) as "an immersion into the megaverse." It's part game room, part lounge: think billiards, ping pong, and darts alongside 4D virtual reality pods.
We stopped in one evening for a game of pool and a couple of drinks, and it made for a nice, low-key change of pace. It is a fun spot to hang out for an hour or two. And it is very much off the beaten path, so it was quiet as well!
The Service
Service throughout the resort was very good - friendly, attentive, and helpful everywhere we went. This is consistent with what I've heard from others about the Grand Wailea. The staff genuinely seems to enjoy their jobs, and it shows.
It was notably a step above comparable resorts I've been to in the Caribbean. Check-in was smooth - the room was actually ready early at 2pm. Housekeeping was reliable, and serviced the room each day. No complaints here at all.
Kilolani Spa (formerly Spa Grande)
We didn't make it to the spa on this trip, but it's such a defining part of the Grand Wailea experience that it feels wrong to leave it out entirely. Quick heads-up if you've stayed here before: what used to be called Spa Grande went through a $55 million renovation and reopened as Kilolani Spa. Same location, same reputation as one of the biggest spas in Hawaii, new name and a much more elevated concept.
The spa has 40 treatment rooms, including three couples' rooms and two deluxe couples' suites. The centerpiece is the open-air Hydrotherapy Gardens - steam rooms, infrared saunas, hydrotherapy pools, and waterfall showers designed around contrast bathing. Access requires either a booked treatment or a dedicated day pass (18+ only), so it's something you need to plan ahead for.
Beyond the treatment menu, there's a sensory decompression room called The Portal, a Hawaiian-inspired hammam, a saltwater flotation lounge, and a Reflection Lounge with ocean views for co-ed lounging. The spa's programming is even tied to the Hawaiian lunar calendar, with treatments and meditation sessions that shift with the moon phase. There's also a full salon with a champagne bar, a wellness café, and a small retail shop. It's open daily from 8am to 7pm.
Grand Wailea Keiki Club
We didn't use the kids club, as my son has mostly outgrown them at this point. but I'll give you a quick overview of what they have available. The Keiki Club is for kids ages 5 to 12, and does have an extra fee. It is not included in the cost of your stay, which is also a bit unusual for this type of resort.
The club runs in half-day sessions. There is a morning session from 9:30am to 12:30pm, and an afternoon session from 1pm to 4pm. The fee during our stay was $93 per session, per child. Activities include arts and crafts, games, and Hawaiian cultural workshops - there are things like ukulele lessons, koi fish feeding, and other hands-on, exploratory adventures rather than just a room full of toys.
Reservations are required, though you may be able to walk-in if they are not busy. And there's a 24-hour cancellation policy if your plans change.
If you have a child under 5, or you want in-room childcare instead of a group setting, the resort also partners with a service called itavi for private, in-room care. I'll be honest - this is something I would simply never do. But the option is there if you need it.
Fitness Center
We didn't end up using the fitness center this trip, so this one's based on research rather than firsthand experience. Frankly, I like to take a vacation from my workout routine when we travel. ;)
But if you're more ambitious than me, you can find a large 2,500 square foot fitness center, which is open 24 hours. Equipment includes Peloton bikes, Technogym machines, and a Theragun recovery station, and access is included for hotel guests.
There's also a solid class schedule if you want something more organized. There is complimentary outdoor yoga on Wailea Beach daily. And for an extra fee, there are paid specialty classes like indoor cycling, Pilates, beach body conditioning, and an aqua-based core/yoga class in the pool.
Who Should I Tip (and How Much)?
You're in the USA, so the same tipping culture applies as at home. But I'll include some guidance here for my international readers. Here's my general guidance:
- Restaurants: You should tip 20% for sit-down service. For takeaway, you don't need to tip, but you can a few dollars if you'd like.
- Drinks: You should tip 20%, or $1-2 per drink if you're ordering beers or simple mixed drinks.
- Valet: $5 when you pick up your car. There is no need to tip when you drop off the car.
- Housekeeping: This is optional - only about ⅓ of hotel guests tip housekeeping staff. But if you would like to do so, $5-10 per night is appropriate. It's generally appreciated if you leave this each day, as the staff can change from day-to-day.
- Tours and excursions: Guides do expect tips, but you don't need to do 20% - that would be quite a lot. A cash tip based on your experience is totally appropriate. We gave $50 for a snorkeling trip with five people, which is more than fair. Obviously the expectation is higher for private tours.
How Grand Wailea Compares to Other Wailea Resorts
If you're trying to decide between Grand Wailea and its neighbors, it mostly comes down to what kind of trip you're after:
Four Seasons Resort Maui at Wailea is the prime pick for honeymooners or a quieter, more adults-oriented luxury stay. Its adults-only pool is often called one of the best in Hawaii, there's no resort fee, and the service is more personal. But it comes at the highest price point, and there's much less for kids to do.
Fairmont Kea Lani is the best match if you want Grand Wailea-level family space on a smaller scale. Every room is a suite with a separate living area, and it still has a waterslide and family-friendly pool, just on a much smaller, calmer footprint.
Andaz Maui at Wailea Resort leans modern and design-forward, with arguably the best beach and snorkeling in Wailea and a more curated dining scene. It skews more toward couples and small families than big groups, and rooms run smaller (as low as 380 sq ft).
Bottom line: if the pool complex is the whole point of your trip and you're traveling with kids, Grand Wailea is hard to beat. If you want quiet, romance, or more personalized service - and don't need a water park - one of the others may be a better fit.
What We Liked the Most (and Least!)
What we loved most:
- The pool! The slides, the grotto bar, and the whole activity pool complex are genuinely incredible and unlike anything you'll find at most hotels
- The views from the room - waking up to the Pacific every morning never got old.
- Convenient grab-and-go food options at the pool and the café made long pool days easy.
What we liked least:
- The sit-down restaurants were disappointing relative to their prices.
- The overall cost - food and drinks in particular feel price-gouged beyond what's reasonable, even by resort standards. And charging for beach chairs at an already expensive resort is just wild.
- A bit inauthentic - this is a luxury resort experience, not a Hawaiian culture experience. You're not going to leave feeling like you really got to know Maui here.
- The early morning chair game - a minor annoyance but a real one.
Would We Go Again?
Yes! If I find myself in Maui again, I think I'd have a genuinely hard time choosing to stay somewhere else now that I've seen what the Grand Wailea has to offer. The pool complex is pretty unmatched, the service is very good, and the location in Wailea is hard to beat.
That said, I'll be honest: we came away a bit undecided on Hawaii in general as a destination. It's beautiful - no question. But as East Coast travelers, the combination of a 10-11 hour travel day each way and the eye-watering price tag of everything once you arrive makes it a hard sell compared to equally beautiful Caribbean spots we can reach in 3-4 hours for a fraction of the cost.
If we lived in California? This would be our annual beach vacation without question. But from the East Coast, it's a big commitment. The Grand Wailea itself, though? It delivers.
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