I’ve Stayed at Maui’s Best Luxury Resort…Here’s How They Rank

There’s a lot you can say about where to stay in Maui, which side of the island is best, which resorts are best for families, for honeymooners, for visitors on a budget, for luxury splurges, etc. and I’ve pretty much hashed it all out on this blog. 

Seriously, no matter what you’re looking for…you’ll probably find it in my archives. 

But today, we’re talking about the best of the best…Maui’s best luxury resorts. 

I’m going to go out on a limb and make a definitive statement here (at least in my PERSONAL opinion). I think Maui has the best luxury resorts in Hawaii

And I’ve put my money where my mouth is, believe me. I’ve stayed at pretty much ALL of the big luxury resorts on Maui.  So I’ve got the LOWDOWN.

This post may contain some affiliate links, which means I’ll make a little money on anything you choose to purchase. But of course, I only recommend my absolute favorites to you. Thank you for supporting the brands that make HulaLand possible.

Maui’s Best Luxury Resorts Ranked

Want the scoop? Well I’m going to give it to you in two parts:

  1. Which side of the island to stay on. There are amazing luxury resorts on the South side of Maui (Wailea) and the West side (Kaanapali and Kapalua) and each cluster is its own little resort bubble. But which one is best??
  2. My favorite specific resorts on Maui. Once you’ve settled on a certain part of Maui…which resort should you pick? 

Let’s get to it!

Wailea vs Kaanapali: Should You Stay in South Maui or West Maui?

Both places offer vacationers sun drenched sandy beaches with great snorkeling, hotels, dining, and activity options. But more specifically…

Stay in Wailea if you want the most luxurious experience possible with lower crowds and an all around more chill vibe. 

Stay in Kaanapali if you want a better deal on accommodations and to be in the middle of the action with a lot of walkable options. 

Need more details? I’ve got them!

The Lay of the Is(land)

Kaanapali is Maui’s original resort area just north of Lahaina in West Maui. 

Since Lahaina was almost completely destroyed by a wildfire in August 2023, this area looks a lot different nowadays. The burned areas of Lahaina are 100% off limits to visitors, but areas that weren’t damaged by the fires started to reopen this spring (more things are opening every day) however the rebuilding is still likely a ways away. 

But the resort areas of Kaanapali, Napili, and Kapalua (all north of Lahaina) were undamaged by the fires and are open for business. 

It’s about a 40 minute drive from the airport and the Lahaina Bypass will take you past Lahaina without getting in the way of locals and workers. While Kaanapali was undamaged by the fires, a huge draw for people staying in Kaanapali used to be its proximity to Lahaina and Front Street for dining, shopping, excursions, etc. While Lahaina will eventually be rebuilt in some fashion, at least for the next few years that’s unlikely to be a factor. 

Wailea is a new(er) luxury resort development on the shores of south maui (just south of Kihei). Wailea is about a 25 minute drive from the airport and even though it’s closer to everything else on Maui (compared to West Maui), it feels a little more tucked out of the way because of its location at the end of the road on the south side. 

What You’ll Love about Kaanapali

Originally developed in the 1960s, Kaanapali was the first tourist hub on Maui, and it’s still where most of the tourists flock today. 

Kaanapali is usually sunny and dry, making for perfect beach weather. The West Maui Mountains loom large, the three-mile beachfront promenade makes it easy to get around and it seems like there’s always something to do. Catamarans pull right up to the beach to take passengers out on snorkeling excursions, but there’s good snorkeling at the far north end of the beach at Black Rock too. 

Also, there’s a wide range of accommodation options so whether you’re looking to splurge on a beachfront resort or save on a condo, you can find it in Kaanapali.

It’s basically vacationland

I’ll get into more details about specific resorts in a bit, but my favorite luxury resort in West Maui is the Ritz Carlton Kapalua

What You’ll Love about Wailea

The coast along Wailea in South Maui is magnificent. If you can swing it, I think Wailea is THE place to stay. On an island that does luxury well, Wailea is the epicenter. Plush beach resorts, fine dining, golf, tennis, and a perfectly manicured landscape absolutely everywhere you turn, this is the Hawaii of your dreams.  

And for that you will pay $$$. 

When I’ve driven people down to Wailea after seeing other parts of the island, they’ve said “now THIS is what I thought Maui would look like.” 

Like I said, Wailea is picturesque but expensive, but there’s a vibe. There’s honestly not a lot going on in Wailea, but in a good way

I’ve stayed at all of the resorts in Wailea, and I’ll get into the details on which ones are my favorites for different scenarios below, but check out these reviews: Four Seasons Maui, Andaz Maui, Fairmont Kea Lani, Wailea Beach Resort

Specific Wailea vs Kaanapali Comparisons

Now that you know the lay of the land and have had the quick rundown on where these two resort areas are and what they’re like, let’s get into some nitty gritty comparisons between the two places…

Best Weather

Kaanapali has pretty idyllic weather all year round (hello Hawaii!), but the south side of the island stays even drier and sunnier than the West side (hence why they’ve started building it up more). 

The average temperatures for Wailea average a degree or two warmer throughout the year, and both get roughly the same amount of “sunny days” but Wailea sees substantially less rain per year than Kaanapali. 

Which means that the rain you’ll get in Kaanapali tends to be brief showers more often whereas in Wailea you’re more likely to go full days without any rain. 

It’s all relative though…and in the summer months (May to October), there’s not going to be much rain in either place. 

So while there’s definitely data that suggests more rain in Kaanapali, given my personal experience (I’ve spent a LOT of time on both sides of the island), I probably wouldn’t pick one or the other based on just the weather. [But once you start going north of Kaanapali to Napili and Kapalua it definitely is more noticeable].

Best Beaches 

If you’re a serious beach bum, you’re going to be happy in either place. Both Wailea and Kaanapali are abundant with sandy, swimmable beaches but let’s hash out the details a bit more. 

The beaches in the Wailea resort area (Mokapu Beach, Wailea Beach, and Polo Beach) are more cove-like with a wide stretch of golden sand bound between two reefs. 

The beaches on the north end of Wailea (Ulua and Keawakepua) are connected and GREAT if you like long walks on the beach. Just south of Wailea (south of where the resorts are) at Makena State Park, Big Beach is one of the best beaches on Maui (although with a pretty gnarly shore break sometimes) and Secret Beach is a fun spot. 

I love the beaches in Wailea and Kihei so much I’ve written a full post on my favorites here

The beaches in the Kaanapali resort area are much longer stretches of sand. Kaanapali Beach is about 3 miles long. You can walk uninterrupted on the sand all the way from the Hyatt Regency to the Sheraton at Black Rock. Black Rock cuts Kaanapali Beach in half between the main Kaanapali Beach area and North Kaanapali Beach. 

Something you’ll definitely want to know about is the erosion that’s started happening on Kaanapali Beach. The south end of the beach (from the Westin down to the Hyatt) has started eroding at a rate of about 2 feet per year. It’s starting to affect the beach walk and they’re currently in talks about how they’re going to handle it moving forward. 

While the beach and beachwalk are all connected and you can walk from the Westin or the Hyatt farther north towards the Sheraton to enjoy a much wider beach, that’s still something to consider. 

The beach on the northside of Black Rock (Royal Lahaina, Honua Kai, Westin Villas, etc) is still wide and sandy. 

Also, two of Maui’s most popular beaches are just north of the Kaanapali area in Napili and Kapalua. Both are pretty wide sandy beaches nestled into protected bays with excellent snorkeling and paddleboarding conditions. 

If you’re staying in Kaanapali, you’ll have to drive to these beaches but they’re very close. 

Speaking of driving, that’s the last point I’ll mention here. If you’re not going to be staying right on the beach or you like to get out and visit different beaches, generally there’s a lot better parking at Wailea beaches than Kaanapali beaches. 

In Wailea, each beach has a pretty decent sized parking lot and the entrances are pretty well marked off the main street. Keawakapu, Mokapu & Ulua, Wailea, and Polo all have designated parking lots with restrooms and showers (Keawakapu only has a shower). Big Beach at Makena State Park has two large parking lots (but you have to pay for parking and entrance here). 

Kapalua Beach has a designated parking lot but it’s not nearly big enough to handle all of the traffic so parking can spill a long ways down the street and parking for Napili beach is just downright chaotic. 

Parking at Kaanapali Beach is super tricky too. The whole beach is fronted by resorts and while they’re required to provide a public right of way and a minimum number of parking spots, it’s not nearly enough to accommodate the number of people that visit each day. More than that though, it’s kind of hard to find them. There’s allotted public parking (free) at Whaler’s Village, the Sheraton, the Westin, the Hyatt, and Kaanapali Alii but it’s a limited amount and it’s not the same as their paid parking garages. There’s usually a second entrance and you kind of have to know where you’re going or have somebody get out and go ask. 

The Hyatt has the largest number of spots but there’s practically no beach down at that end any more. 

In the past I’ve always parked at the Sheraton since that’s the best part of the beach. The free parking spots are in a different part of the garage than the paid/guest parking and you don’t go through a gate to access. When you drive around the loop at the end of the road in front of the Sheraton, their paid garage is on the right and then the turn in for the free spots is down a bit farther on the right. 

Honestly, if I can’t find a free spot here I usually just end up paying to park in the Sheraton garage since we usually have a lot of beach gear and we don’t want to walk a long ways down the beach dragging everything. 

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Best Snorkeling

Kaanapali has some of the flashiest snorkeling spots on the island plus it’s in close proximity to a lot of good spots in West Maui, but I really like the snorkeling around Wailea and Makena too. 

Black Rock at the north end of Kaanapali Beach (in front of the Sheraton) is a favorite spot on the island. The water is pretty calm at this end of the beach, there are usually plenty of people out here snorkeling (I consider that a plus – I never want to be the only person out snorkeling), and if you don’t have your own gear you can rent it from the stand at the Sheraton. It’s not uncommon to see turtles here too. 

And again, if you’re willing to drive to nearby Napili Bay or Kapalua Bay those are big crowd pleasers too. They’re both pretty protected bays so it’s usually like snorkeling in a lake. And turtles usually hang out here too. 

And it’s more of a drive, but Olowalu (south of Lahaina) and Honolua Bay (north of Kapalua) both have great snorkeling. But Honolua Bay is only good for snorkeling if the waves aren’t breaking. Also, the parking situation is kind of tricky here and you’ll likely end up having to park on the side of the road (don’t leave anything in your car!) and walk down to the bay’s entrance. 

In general, I’ve found snorkeling in Wailea to be more convenient (easier parking, beach access, rentals at the resorts, etc.) but the reefs usually aren’t as protected feeling and sometimes you have to snorkel out around the reef farther from the beach which I don’t love. 

I’m a really strong swimmer but I have a healthy respect for the ocean and honestly often when you hear about a tourist drowning or a shark attack, it’s in this area. 

I like snorkeling at Ulua Beach in front of the Andaz because the reef has a bit of an arm that makes the south end of the beach feel kind of protected plus there’s usually several people out there snorkeling. 

Conditions around Wailea Beach and Polo Beach are often too rough for snorkeling but the best conditions will be early in the morning. 

The big snorkeling draw in south Maui is Turtle Town in Makena. A lot of the snorkel boat tours that go out to Molokini make a stop at Turtle Town and while it’s a bit off shore, you can still snorkel in the same area from the shore. The best place to access Turtle Town is at Makena Landing which is just a short drive from the resorts and condos in Wailea. 

Best Dining & Nightlife

“Nightlife” is a relative term on Maui. In the traditional sense, there really isn’t any. But for the sake of this comparison, let’s talk about anything to do after dark (which could be 6PM depending on the time of year ; )

Honestly, this is where Lahaina’s absence is going to be most felt. A huge draw to staying in Kaanapali was the proximity to Lahaina and being able to go to Front Street for dinner, drinks, shopping, walking around, getting ice cream, etc. That’s all gone now and honestly it still remains to be seen how things are going to feel in Kaanapali once the tourists return in full numbers. 

In the Kaanapali area (and even up to Kapalua) there just aren’t a ton of restaurants that aren’t attached to the resorts and given the large number of condos, dining options might be pretty slim for a while. 

Your best option is currently going to be Whaler’s Village which has a handful of sit down restaurants and a small food court type area. It is the lively hub of Kaanapali Beach but I’m not sure it’ll be able to handle the crowds now that Lahaina isn’t also an option. 

Wailea’s proximity to Kihei means that right now it’s definitely the clear winner when it comes to dining and nightlife options. 

I’ve got a full post about my favorite restaurants in Wailea and Kihei here

Best for Honeymoons or Luxury

The clear winner here is Wailea. Wailea is hands down the most luxurious resort area in all of Hawaii, not just Maui. 

There’s a slew of fantastic 5 star resorts here (The Four Seasons and Andaz being at the very top) plus an entire ecosystem of restaurants, luxury luaus, spas, boutiques, golf, tennis, etc. 

Kaanapali has some great beach resorts, but they’re really all in the mid range “big box” category (Sheraton, Westin, Hyatt). 

The only luxury option that Kaanapali currently offers is the new Hokupaa Tower at the Westin. It was built to compete in the luxury market and the new 217 room tower is definitely luxurious. The rooms are heads above what you’ll find in the area and the private infinity pool on the lanai is pretty dreamy. But it still feels a bit like an oasis in a desert luxury wise if you know what I mean. 

For REAL luxury on the West Side, you’ll need to go just a tiny bit further north to Kapalua. The Montage and the Ritz Carlton are both fabulous. 

Best for Bargains/Condos/Value

You rarely see “Wailea” and “bargain” in the same sentence. While there are definitely more reasonably priced condos off the beach in Wailea, you’ll find far better value for your money in Kaanapali. 

On main Kaanapali Beach, there are a handful of great condo-tels plus if you’re willing to venture farther north there are plenty of bargains to be had. 

In this post, I’ve got sooooo many recommendations for condos to fit all budgets in Kaanapali and West Maui but also South Maui. 

Best for Location

Let’s break this down into two parts: 1) Location on the island relative to other attractions, and 2) What else is close by.

As far as location on the island relative to other attractions, the winner here definitely goes to Wailea. Its location in South Maui makes it about 30 minutes closer to (what I think are) the island’s must sees. Haleakala, the Road to Hana, Paia and the north shore, the upcountry…I think these are the best areas of Maui and even if you only spend a couple of days exploring this part of the island, you may appreciate being a bit closer. 

Now don’t get me wrong…Wailea isn’t exactly close to all of these things, but it is closer than West Maui. 

One of my major drawbacks about staying in West Maui is how far it is from everything else on Maui (i.e. my favorite things). And besides the distance, there’s only one road in and out of West Maui so a bad accident can really shut things down. Not that that’s super common, but it is a possibility. HOWEVER, even though it’s a longer drive from Kaanapali to the other part of the island, the good news is that it’s such a beautiful drive that you may not mind. 

Now onto the second point here…what else is close by. 

I mentioned this earlier, but close proximity to Lahaina used to be a major selling point for staying in Kaanapali. Lahaina was the hub of tourism in West Maui and now that that’s gone, it remains to be seen how tourism is going to respond in the area. There are definitely going to be fewer restaurant options and less shopping and “things to do.”

Wailea isn’t exactly known for being a bustling hub of activity, but Kihei is a pretty sizable town just to the north and there is always a lot going on there. If you’re wanting to break out of the resort bubble and try some more low key or local food options, Wailea’s proximity to Kihei is definitely an upside. 

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Best for Walkability

One of my favorite things about both Wailea AND Kaanapali is how walkable they are. 

Besides wide sidewalks that line the main roads through the resort areas, both areas also have a beach walk that’s perfect for early morning walks when you’re still acclimating to the time change, just exploring the area, or walking from your resort to another spot for dinner or shopping. 

I think overall Kaanapali feels more walkable though, as long as you’re on the main stretch of beach staying somewhere between the Sheraton and the Hyatt. Whalers Village is kind of the hub of activity in this area and it’s a great shopping complex plus just general gathering area (live music, etc.). 

You can also cut through the Sheraton and connect to a walkway along North Kaanapali Beach (at the Royal Lahaina), but it’s not quite as bustling up there. 

The Kaanapali Beach Walk is a great amenity and it’s super convenient for getting around, but in general I think it’s much less scenic than the Wailea Beach Walk. 

While the Kaanapali Beach Walk is pretty flat, the Wailea Beach Walk has better views and a better vantage point. You feel like you’re up a bit higher and can really take in the vistas. 

While the Wailea Beach Walk runs from Polo Beach (Fairmont Kea Lani) to Ulua Beach (Andaz) and it’s a GREAT activity to get out and walk, it can feel a little far if you’re using it to walk back and forth to dinner or what not. The sidewalk out in front of the resorts (along the main road in Wailea) is actually a more direct route to take. 

And while there’s more development in Wailea off the beach like the Wailea Tennis Club, the Wailea Village (shopping center), the Wailea Gateway Shopping Center (Monkeypod), etc. It’s all uphill from the resorts and I think it’s a little far to walk (especially after dark). But most of the resorts in this area have courtesy cars that will take you anywhere you want to go. 

So bottom line…both resort areas are walkable to a certain extent, but they’re both also pretty spread out and you’ll probably still need a car. Especially if you’re visiting other parts of the island. 

Best for Activities

Both areas have plenty to do and you’ll find snorkeling, paddle boarding, outrigger canoe rides, kayak eco tours, etc in both places. Both have golf, tennis, and shopping plus places to hear live music. 

Snorkel tours to Molokini and Turtle Town leave from Makena (Kai Kanani’s Sunrise Snorkel Tour is one of my favorites) and the Kihei boat ramp. And snorkel tours to spots on West Maui leave from Kaanapali Beach. 

Best Shopping

I love to talk about shopping! Here’s the scoop: Wailea has the Shops at Wailea and Kaanapali has Whalers Village. 

As much as I love Wailea, I personally think that the Shops at Wailea is kind of a disappointment. Maybe because it’s off the beach and the Wailea Beach Walk, but it just never quite seems like a hub of activity and they can’t quite seem to keep it filled with open stores. There’s a high concentration of designer shops here (Louis Vuitton, Gucci, Bottega Veneta, Prada) and I’m sure that hits a certain segment of shoppers, but I think there’s a lack of more local beach boutiques. It’s fine but it’s just nowhere near as good as I think it could be. Plus none of the restaurants there really have ocean views. 

Whalers Village in Kaanapali, on the other hand, I LOVE. It sits right on the beach and with the beach walk, it’s just a natural gathering place. There are a few great restaurants here (my favorite is the Monkeypod) and they all have ocean views. Plus they’re always able to keep it full of good shops. Yes, there are some higher end shops (Louis Vuitton, etc.) but it’s mostly more accessible but still either Hawaiian or beach/tropical brands. 

In Wailea, besides the Shops at Wailea, Wailea Village has some shops that I really like (LOVE Bikini Mart) plus the resorts have great boutiques. Bikini Bird just opened in the Grand Wailea (they have the largest concentration of shops in one resort) plus the Four Seasons, Andaz, Fairmont, and Wailea Beach Resort all have nice boutiques. 

Sunsets & Views

Both Kaanapali and Wailea face west so they both have pretty decent sunset views although as the sun shifts throughout the year sometimes you’ll be seeing the sun set behind Lanai or Koolawe instead of into the ocean. 

Best Golf

Both Wailea and Kaanapali have great golf, but I’ve got to give the edge to Kaanapali here…but mostly because of the proximity to Kapalua. Yes, Kaanapali has two courses at the resort, but it’s also a very short drive up to Kapalua where you’ll find some of the best golf courses in the world

It’s probably not for beginner golfers, but the Plantation Course at Kapalua is home to the PGA’s Sentry Tournament of Champions every January. Plus the Bay Course is also a championship course. 

The Wailea Golf Club is home to three courses: Wailea Gold (a championship course), Wailea Blue (they offer a sunset golf cart tour here that I’ve got my eye on), and Wailea Emerald (a family friendly course). 

Best Tennis

Maui isn’t really a tennis island but there are a couple of good options here. There’s the Wailea Tennis Club in Wailea (probably walkable from the Wailea Beach Resort but a short drive from other resorts). It’s also really close to the Grand Champions condo complex. They offer private lessons and daily clinics. 

Besides the Wailea Tennis Club, there’s an onsite tennis facility at the Four Seasons operated by Darin Zerbe. It’s open to anyone not just resort guests and the surface is artificial turf which could be an interesting change (I’d never played on that before). 

In Kaanapali, by far the best option used to be the Tennis Ranch at the Royal Lahaina. They’ve operated for 30 years and even hosted some smaller pro tournaments. But a few of their pros were impacted by the Lahaina fires and they’ve decided not to renew their lease at the Royal Lahaina. It remains to be seen if someone else will take on the operation and reopen. 

In Kapalua there’s the Kapalua Tennis Garden. They have 8 tennis courts and 4 pickleball courts plus clinics and daily drop ins. 

Crowds

It’s hard to call either Wailea or Kaanapali crowded (especially in terms of Waikiki on Oahu), but the large number of condos in Kaanapali definitely make it feel more crowded than Wailea. 

And as I mentioned before, some of the most popular beaches (AKA the most beautiful) like Kaanapali, Kapalua, and Napili can be crowded with limited parking. 

The beaches in Wailea tend to be much less crowded and quite a bit more accessible than those on the West side (more parking and better marked). 

To Split or Not to Split

If you’ve read through everything about Wailea and Kaanapali and you really still can’t decide, a lot of people wonder about splitting their trip and staying in Wailea part of the time and Kaanapali for part of the time. 

I don’t usually recommend splitting your stay among different parts of the island (especially the south side and west side) for the sake of trying to save time driving to do activities. A lot of people ask if I would recommend staying on the west side to do the things over there and then moving to the south side so they’re closer to Haleakala, Hana, and the north shore. But I don’t. 

These two areas are both touristy, beachy areas so just pick one place and stay there the whole time even if it means an additional 30-minute drive going places. It’ll be less of a hassle than moving. Besides, even if you’re staying in Wailea, it’s still not that close to the east side of the island.

Here’s when I do recommend a split stay: if you’re wanting to experience a high-end luxury resort, but you can’t swing the bill for your whole stay. If you have a week, and you want to do a fair bit of exploring the island, but also enjoy a stay at a luxury resort where you never leave the beach/pool, I would suggest splitting your stay 4 nights at affordable/central accommodations and 3 nights at a nice resort.

On my last trip to Maui, I stayed the first three nights at a rental in Paia (you could also stay at the Paia Inn) and did sunrise at Haleakala, toured Maui Wine and the upcountry, hung out on the north shore with some turtles, explored Paia and Makawao, drove to Hana, had dinner at Mama’s Fish House, and swung by the Iao Valley before checking into the Four Seasons in Wailea for 3 nights and doing NOTHING.

Doing your trip this way means you hit the ground running and go, go, go but it also means you don’t have to pay for a full week at a luxury resort when you’ll be out exploring. Something to think about!

My Favorite Maui Luxury Resorts

Okay, now onto the details. Since Maui’s luxury resorts are split between these two different parts of the island (Wailea and Kapalua), picking which side you want to stay on will help narrow down your options. 

If you’ve read through this post so far and you’re leaning towards the West Side, you’ve got two options: 1) the Montage Kapalua and 2) the Ritz Carlton Kapalua. The Montage is more exclusive and more luxurious to be sure (it also has access to Kapalua Beach which is phenomenal), but it’s one of the most expensive resorts on Maui. The Ritz Carlton Kapalua is quite a bit less than the Montage, but still really nice. Read my full review here

For my money (in this price range), when I want luxury, I head to Wailea. 

Everybody has different opinions and things they like or don’t like, but having stayed at all the big resorts in Wailea, here is how I would rank them:

#1 Four Seasons Maui

I think the Four Seasons is the gold standard, the cream of the crop, the yardstick which all other luxury resorts are measured against…especially in Wailea. 

The whole place just has an “air” about it that’s hard to put your finger on but it’s the perfect intersection of over the top luxury and casual friendliness. 

The adults only serenity pool is probably the best pool anywhere in Hawaii. I love a good infinity pool, but this one is over the top with the swim up bar and amazing view of Wailea Beach. 

The service here is what really sets it apart. I’ve never experienced anything like it in my life. 

This is also the only resort in Wailea that doesn’t charge a resort fee (or charge for cabanas around the pool-they’re first come first serve), but the overall price is $$$ and other amenities and the food options here are more of a premium than at other resorts. 

Read my full review of the Four Seasons here

You can book the Four Seasons Maui here

#2 Andaz Maui

The Andaz just might rank as #1 if we’re talking about the actual property, but their service isn’t quite up to par with the Four Seasons so I think that bumps it down to #2. But the style of these two resorts is so radically different that I would probably go with whichever one you’re more drawn to. The Andaz is very modern and the Four Seasons is much more traditional. 

The Andaz feels a bit more out of the way since it’s down at the end of Wailea. If the beach is important to you, I think the Andaz is on the best beach in Wailea. The snorkeling is good, it’s not as crowded as others like Wailea Beach, and it’s a really long beach that’s perfect if you like to take walks. 

For me, the pool set up also wins as overall best. There are three infinity pools plus a lagoon pool and a separate adults only pool over by the spa. One of the infinity pools even has a hot tub in it. 

While the Four Seasons’ infinity pool is my top pool spot to be, it’s adults only and generally has limited seating for the number of people who want to be there. The Andaz infinity pools aren’t quite as good (mostly they don’t have prime views of the beach itself), but there are three of them and seating is a lot more plentiful. None of the main pool areas here are adults only but in general the Andaz attracts a lot fewer kids than the Four Seasons so it’s not super necessary. 

Read my full review of the Andaz here

You can book the Andaz here

#3 Wailea Beach Resort

In my mind, while the Four Seasons and the Andaz are very comparable and within a stone’s throw of each other, there’s a lot more separation as we move down the list. 

I would rank the Wailea Beach Resort as my #3 pick, but I just want to be clear that while I don’t think there’s a ton of separation between #1 and #2, there is a lot of separation between #2 and #3, if that makes sense. 

Aesthetically, the Wailea Beach Resort has a modern vibe that’s more in line with the Andaz than the more traditional properties in Wailea (Four Seasons, Grand Wailea, Fairmont Kea Lani) and while it’s definitely a very high end resort, I wouldn’t call it luxury. 

The property is beautiful and built on a very big scale, but it’s designed to be more of a self serve/fend for yourself set up instead of being service oriented which I think is what usually separates high end from true luxury. 

I’ll be honest, what I love most about the Wailea Beach Resort is that it’s a Marriott property and since I have status with Marriott I can either cash in points to cover a very expensive stay, or at least get a nice chunk of points for my stay if I pay cash. 

If the beach is of utmost importance to you, the Wailea Beach Resort isn’t directly on the beach (it stretches along a rocky bit of coastline) but it’s a short walk to two great beaches and they do chair setup at Wailea Beach. 

Since it’s not “on” a beach though, they’ve got more oceanfront real estate than pretty much every other in Wailea. Pretty much every pool (except the Nalu Adventure Pool with the slides and waterfall) has ocean views which I LOVE. 

The biggest draw back of this resort are the rooms. I’d rank them dead last in Wailea. They’re not bad, but they’re not good. Definitely not what you’d expect from a $1000/night resort on Maui. 

Read my full review of the Wailea Beach Resort here

You can book the Wailea Beach Resort here

#4 Fairmont Kea Lani

In many ways, the Fairmont has a much stronger understated luxury vibe than the Wailea Beach Resort, but overall I’d still rank it below. 

Let’s start with the strong points…I think the Fairmont Kea Lani has the best rooms in Wailea. That is, the best standard price, entry level rooms (I’m sure if you’re paying $$$ for a suite or a villa at the others they knock it out of the park). EVERY room at the Fairmont Kea Lani is actually a suite with a separate living area and that is a pretty big deal. They’ve also ALL been renovated in 2023 and they are NICE. AND pretty much every room has an ocean view or partial ocean view (except for low level rooms that aren’t going to be high enough for a view…basically, every room faces the ocean). 

While I LOVE the rooms at the Fairmont, I don’t spend very much time in my room (even when I’m spending most of my time at the resort) so that doesn’t quite mean enough to me to bump it up higher on the list. 

What I don’t love about the Fairmont is the pool situation. Yes, there are several pools including a water slide two of them, a swim up bar, and an adults only pool, but all of the pools are tucked up back into the resort and the resort grounds aren’t really terraced so when you’re at the pools, you’re just kind of looking up at the resort, not out at the ocean and beach. 

You actually have to stroll down towards the beach pretty intentionally before you even see it. 

It’s not awful, but just not my favorite. And while they’re doing a lot of renovations on the property, it’s just not quite up to the standards as some of the other places in the area. It’s definitely built in the same traditional style as the Four Seasons and the Grand Wailea, but it just doesn’t really compete with them in terms of luxury and service (Four Seasons) or scale and amenities (Grand Wailea). 

But depending on the price and how much you value the room setup, it can be a very good option. 

Read my full review of the Fairmont Kea Lani here.

You can book the Fairmont Kea Lani here

#5 Grand Wailea

I know so many people are going to be screaming at me for putting the Grand Wailea close to the bottom of my list when it’s usually talked about as “the” place to stay on Maui…but I’ve got opinions ; ) 

First of all, the Grand Wailea and I go waaaay back. Like, back to childhood. I used to watch this show on the Travel Channel with Samantha Brown called Great Hotels and she went to Hawaii (the most exotic place I could imagine at the time) and stayed at the fabulous hotel called the Grand Wailea and I was sure it must be the nicest hotel anywhere in the world. 

Fast forward to when I lived on Maui (way before I started this blog) and I got the chance to stay here with some friends and honestly, it probably was the nicest place I’d ever stayed at the time. By a long shot. 

But fast forward more to now, when I’ve made it my job to stay at luxury resorts and I just have more perspective. 

So here’s the scoop…the Grand Wailea is the most famous (let’s call it the flagship) resort in Wailea partly because of its size and “grandeur” and partly because it was the first. 

Grand really is the best way to describe this resort. 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 got everything you could want in a resort, but its 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. 

But here’s the deal…I don’t usually travel with kids so that’s not a huge selling point for me personally when I’m picking a place to stay. 

I will be completely honest…I have a bit of a love/hate relationship with this resort. I LOVE a big, comfy resort with a lot going on. 

But I’ve always found their service to be pretty lackluster. 

Most of the employees are friendly and helpful when you directly cross paths with them, but this isn’t the kind of place where they go out of their way to be friendly and helpful. And it’s also one of the few “high end” properties where I’ve actually had a few less than stellar experiences with staff members. 

From the valet to restaurants to shops to lobby concierge, I’ve had a few run-ins where it was pretty obvious that they don’t really care whether you’re there or not. And at THE MOST EXPENSIVE hotel in Wailea, I don’t love that. 

Also, while it’s very “grand,” parts of it can feel a little dated. In complete fairness, I haven’t stayed here since 2014 (although I’ve been there quite a bit for dining, shopping, luau, strolling through, etc) and they’ve been hitting the renovations pretty hard lately so I’m making it a priority to go back for another full stay in 2024 to give it another shot. 

So anyways, the Grand Wailea definitely has the “wow factor”, but for me, when I’m comparing this place to the Four Seasons next door or the Andaz (or even the Fairmont and Wailea Beach Resort), the customer services pales in comparison (but the price doesn’t ; ) 

So when I’m traveling without kids, this is not really an option that I’d consider in Wailea. 

You can book the Grand Wailea here

#6 Hotel Wailea

Okay, I said earlier that the Hotel Wailea is an outlier, and it is. And that’s why I’ve put it at the bottom of this list. Also, full disclosure…I’ve been here for dinner and walked around the property but I haven’t stayed here yet. 

Here’s the deal…the Hotel Wailea is a VERY upscale, small, boutique hotel on the slopes of Haleakala above Wailea. 

It’s just in no way comparable to the big beach front resorts with THOUSANDS of people staying there. This feels more like a private villa estate tucked away from the prying eyes of the public haha. 

It is sooooo nice, and I LOVE going there for drinks and dinner and someday I do want to do a short stay there (I can’t see wanting to stay for more than 2-3 nights) but I’m not really sure how I would insert it into this list. 

It’s the only adults only hotel on Maui (16+) so if you’re honeymooning or just looking for a more intimate getaway, it’s perfect. And while it’s not on the beach (and not really within walking distance), there’s a private luxury shuttle that takes you to Wailea Beach where the hotel has chairs and umbrellas setup for guests. 

In terms of luxury, it’s on par with the Four Seasons, but just a different experience. If you want a truly unique, highly personalized, design-centric experience, it fits the bill. 

You can book the Hotel Wailea here

Best Hotels in Wailea WITH KIDS

While I don’t personally have kids, I do have a lot of kids in my life and often travel with them. So I get travel with kids. And here’s the deal…if you’re traveling with kids, my ranking pretty much flips on its ear. 

#1 Grand Wailea

You just cannot beat the Grand Wailea if you’ve got kids. This place is practically a waterpark. With nine different pools spread across different levels that are connected by a lazy river with rapids and currents, it’ll keep the kids busy for days. There’s a pretty serious water slide (must be 48” tall) plus a pool complex that includes smaller (but still pretty significant) slides, a rope swing, a white water rapid slide, a sandy beach, swim up bar, caves and so many waterfalls.

 

The scale of this place is just massive. Oh yeah, and it’s just steps away from a great sandy beach which usually has waves that are prime time for boogie boarding. 

Everything about this place is kid friendly, and while there is an adults only pool it’s just all so kid-centric that I’m always surprised when I hear people recommend it as a honeymoon resort. It’s the #1 place to stay on Maui with kids, but close to the bottom of my list if you’re on a honeymoon. 

You can book the Grand Wailea here

#2 Wailea Beach Resort

I think the Wailea Beach Resort has the most low key “accessible” vibe in Wailea (i.e. people who don’t regularly stay at luxury resorts or might feel uncomfortable at a place like the Four Seasons are going to feel right at home here) and that translates well to traveling with children. 

They’ve got a great kids pool area with the biggest/tallest/fastest slides on Maui plus a whole water play area and other “normal” pools besides the kids pool and the adults only pool. 

The location is great and I think they’ve also got the best grab and go food options. Besides pool service, there’s a food truck by the kid’s pool plus a Starbucks in the lobby and a mini ABC Store (quick place where you can grab bottled drinks, snacks, etc.) plus you’re within walking distance to the Shops at Wailea where there’s a full ABC Store and the Island Gourmet Market which is basically a small grocery store and has a large prepared food section and even a grill where you can get breakfast, burgers, pizza, etc. 

I know you don’t always want to have to order $20 grilled cheese sandwiches for kids at the pool and wait 30+ minutes for them to arrive so it’s good to have quick options. 

The Wailea Beach Resort also has a really nice game room right off the lobby that’s got arcade games, air hockey, pool, foosball, etc plus things like nightly movies. 

You can book the Wailea Beach Resort here

#3 Fairmont Kea Lani

Every room at the Fairmont is actually a suite with a separate living area which is GREAT if you have kids. 

There’s a large pool area with a pretty good waterslide and a small market near the pool with grab and go snacks, drinks, breakfast, sandwiches, etc. 

You can book the Fairmont Kea Lani here

#4 Andaz

The Andaz isn’t necessarily kid friendly but it’s not not kid friendly. I’ve noticed mostly people with younger kids staying here (let’s say under 3 or 4) that are content to splash in the pool (the lagoon pool has a zero entry side) but don’t necessarily need a whole waterpark to keep them entertained. 

If you’ve got smaller kids or older kids (who’ve maybe grown out of the waterpark), I think the Andaz has better overall pool options than the Four Seasons that will suit the whole family (the Four Seasons’ best pool is adults only).

Also, the snorkeling off the beach at the Andaz is really good and they have free snorkel rentals for resort guests which is great for older kids. Plus they do complimentary outrigger canoe rides (sign up in advance) and have pretty good water recreation options (SUP rentals, snorkel tours, etc.). 

You can book the Andaz here

#5 Four Seasons

Generally speaking, the Four Seasons is a very family friendly brand and the resort in Maui is no exception, but I’ve still ranked it at the bottom of the list just because they don’t offer a lot of the same amenities that appeal to kids that other places in the area do. 

There’s only a small waterslide (like, for babies) and the main family pool is just a little dull compared to what they’ve got going on over at the Grand Wailea and the Wailea Beach Resort. 

If your kids are small (toddler age), they’ve got a great setup, but it’s definitely not the waterpark vibes they’ve got going on next door. But that can also be a plus. 

They do have a GREAT open air family game room setup with a pool table, foosball, video game room, etc. though. 

You can book the Four Seasons here

A Few More Random Things

I’ve covered a lot here, but here are a few loose ends that might be good to know: 

The Four Seasons is the only resort in Wailea with on property tennis courts. They’re artificial turf and the program is run by a third party company and anyone can go to drills, clinics, and lessons but obviously it’s most convenient if you’re staying there. The Wailea Tennis Club is also in the area and is open to day guests. It’s closest to the Wailea Beach Resort, but you’d probably want to drive. 

There’s great golf in Wailea, but none of it’s based at a resort so you’ll still have to drive no matter where you’re staying. 

As far as spas go, the Grand Wailea has always had far and away the best spa facilities, but they’re undergoing a MASSIVE renovation and currently what you can book are these little spa bubbles (you just get access to one private room). I assume once the renovation is complete it’s still going to be the place to go. I have a lot of feedback (including people who used to work in spas in Wailea) that the Willow Stream spa at the Fairmont is the best place to go as far as actual treatments are concerned but their facilities don’t have all the bells and whistles. I wasn’t super impressed with the spa at the Four Seasons (facility or treatment), and I wanted to try the Andaz on my last trip but they were booked up. They seem to maybe be a sweet spot of super nice facilities and good treatments though. 

And I’ve mentioned loyalty programs a bit, but here’s the full rundown: 

Wailea Beach Resort = Marriott

Andaz = Hyatt

Grand Wailea (Waldorf Astoria) = Hilton

Want to read more posts about Maui? I’ve got plenty!

Things You Can ONLY Do on Maui // 4 Day Maui Itinerary // My Favorite Road to Hana Itinerary // Things to Do Upcountry // Tips for Sunrise at Haleakala National Park // Snorkeling Molokini Crater // Whale Watching

My Favorite Hotels on Maui // Where to Find Condos on Maui // Wailea vs Kaanapali // Every Resort in Wailea Ranked // Four Seasons Maui Review // Andaz Maui Review // Fairmont Kea Lani Review // Wailea Beach Resort Review // Four Seasons vs Andaz Maui // Andaz Maui vs Wailea Beach Resort

Best Restaurants in Wailea // Best Breakfast in Wailea & Kihei // Mama’s Fish House // Best Luaus in Wailea

My Favorite Things to Do in South Maui // Best Beaches in Wailea & Kihei // Road to Hana Tips // Driving the Backside of the Road to Hana // Where to See Turtles on Maui

Maui vs Kauai // Everything You Need to Know BEFORE you go to Maui

Here’s one more really important thing you need to know before your Hawaii trip…

Reservations You Need to Make BEFORE Your Hawaii Trip

You’ve got your airfare, hotel, rental car and your big activities booked, so you should be good to go, right? Wrong!

Travel is BOOMING in Hawaii so a lot of state and national parks used the closure and reopening to institute reservation systems at some of the island’s most popular spots to make things a little more sustainable.

That means that there are now over half a dozen sites (beaches, trailheads, etc.) that require advance reservations. And some sell out well before you arrive on the island so you really need to have some sort of a plan.

I recently saw somebody in a Hawaii travel group post in a panic that they didn’t know they had to make reservations for things in advance…they thought they could just show up and “go with the flow.” I was tempted to say, well, “as long as the flow doesn’t take you somewhere that requires reservations, you can!” ; )

But I don’t want YOU to be that person, so I’ve pulled together a list of all the places you need to reserve entry in advance (plus all the details on booking windows, price, links, etc.) and a handful of popular tourist hotspots that book out really far in advance too.

Haleakala National Park (Maui)

To visit Haleakala National Park for sunrise at the summit, you must make reservations in advance here.

Reservations are required to enter the park gates between 3AM and 7AM (sunrise hours).

Online reservations are $1 per reservation/vehicle PLUS you’ll pay the park entrance fee of $30/vehicle when you arrive (National Park annual passes are also accepted at the gate).

The reservation booking window opens 60 days in advance at 7AM HST. There are also a limited number of tickets released two days before.

You can make one reservation every three days with the same account. So if you want to make reservations for back to back days (in case of weather/conditions), you’ll need to do so with separate accounts (email addresses).

If you can’t get reservations for sunrise, you can enter the park anytime after 7AM without reservations. The summit is spectacular during the day and you don’t need reservations for sunset.

I strongly recommend creating an account before and making sure you’re logged in at 7AM HST because it’s not uncommon for reservations to sell out quickly.

Waianapanapa State Park (Maui)

To visit Maui’s famous black sand beach at Waianapanapa State Park on the Road to Hana, you must make reservations in advance here.

Reservations are required to visit the beach and are distributed in windows from 7AM-10AM, 10AM-12:30PM, 12:30PM-3PM, and 3PM-6PM. And they are pretty strict about exiting by the end of your window time (you can arrive anytime within your window).

It’s $5/person to enter plus $10/vehicle to park and those fees are paid when you book your time slot.

Reservations open up 30 days in advance.

Iao Valley State Park (Maui)

To visit the lush, green mountains and hike at Iao Valley State Park, you must make reservations in advance here.

Reservations are offered for 90 minute time slots beginning at 7AM and ending at 6PM. They ask that you arrive within the first 30 minutes of your time slot.

Entry is $5/person plus $10/vehicle to park.

Reservations open up 30 days in advance.

Diamond Head (Oahu)

To hike to the top of Waikiki’s famous Diamond Head, you must make reservations in advance here.

Reservations are offered in two hour increments beginning at 6AM (6AM-8AM, 8AM-10AM, etc.) and ending at 6PM. If you’re parking onsite, they ask that you arrive within the first 30 minutes of your reservation window.

Entry is $5/person plus $10/vehicle to park.

Reservations open up 30 days in advance.

Tip: I recommend booking one of the first two time slots because there isn’t much shade on this hike and it gets pretty hot.

Hanauma Bay (Oahu)

To snorkel at Oahu’s pristine Hanauma Bay, you must make reservations in advance here.

Entry times are staggered in 10 minute increments from 7AM to 1:20PM with roughly 1000 slots being assigned in advance every day.

Reservations can be made two days in advance and they open at 7AM HST. They’re usually gone in minutes (if not seconds).

If you’re unable to get an advanced reservation, you can try for a day of, walk in ticket. They open at 6:45AM and they only have a limited number available. Everyone in your group needs to be present when you purchase your tickets in person.

There are no reservations for parking and it’s first come, first serve. $3/vehicle.

It’s $25/person to snorkel at Hanauma Bay (12 and under, active military, and locals with HI ID are free).

The Hanauma Bay Nature Preserve is open Wednesday through Sunday (CLOSED MONDAY AND TUESDAY) from 6:45AM-4PM. Last entry is at 1:30PM, the beach is cleared at 3:15PM and you have to leave the facility by 4PM.

Jellyfish patterns can also affect whether or not the bay is open so double check the day before/day of.

USS Arizona at Pearl Harbor (Oahu)

If you want to take the boat tour at Pearl Harbor out to the USS Arizona, it’s recommended to make advance reservations here.

Online reservations are guaranteed a specific boarding time to go out to the USS Arizona. If you’re unable to get an advance reservation, you can wait standby when you arrive. The line could be short (15 minutes or so) or long (hours) and it just depends on the day (if they’re having problems with the loading dock sometimes they don’t take many from the standby line) and the time of day.

Reservations are supposed to open up 60 days in advance, but keep an eye on your exact dates, because lately they’ve actually been opening up about 57ish days in advance???

They also release a small batch of tickets the day before.

The boat ride out to the USS Arizona is free, but it’s $1 to make the reservations online.

They recently started charging $7/vehicle for parking at Pearl Harbor.

Haena State Park / Kalalau Trail (Kauai)

If you want to hike Kauai’s famous Kalalau Trail, you must make advance reservations here.
You’ve got three options here:

1) Parking & Entry: This is the most flexible option and also the most limited. THESE RESERVATIONS SELL OUT IN LESS THAN A MINUTE. There are three time slots available: 6:30AM-12:30PM, 12:30PM-5:30PM and 4:30PM to sunset. You can purchase multiple time slots if you want to stay longer. It’s $10/timeslot (parking) plus $5/person and you have to reserve every person when you initially book. Everybody has to arrive in the same car and your ID needs to match the reservation.

2) Shuttle & Entry: If you can’t get parking at the trailhead, there’s also a shuttle option. Shuttle reservations are $35/person (16+), $25/person (ages 4-15), 3 and under can ride free. The shuttle runs every 20 minutes 6:20AM to 6:40PM.

3) Entry Only: If you’re a Hawaiian resident (with HI ID) or someone WITH a Hawaiian resident, you can purchase entry only for $5/person with no advance reservations. Also, if you’re walking or biking to the trailhead you can do this option. But there is NOWHERE to park in the area to walk in. So this really only works for those with bikes or who are staying close enough to walk. They will tow your car if you park outside the designated areas.

The reservation window opens 30 days in advance at 12AM HST. The parking & entry option usually sells out in a minute, but the shuttle availability will last longer.

There are a TON of FAQs here including the possibility of snagging a canceled reservation.

Other Things to Book in Advance

Hawaii is a busy place these days! Besides the state and national parks above, here’s a handful of miscellaneous things you should make reservations for in advance (if they’re on your radar):

Mama’s Fish House (Maui): The iconic spot is the most popular restaurant in Hawaii and dinner reservations usually start filling up about 6 months in advance (they open up bookings 18 months in advance). Make reservations through their website and if the dates you want are already booked, you can join a waitlist. Most people have pretty good success getting in on the waitlist (even if it’s for lunch).

Old Lahaina Luau (Maui): Honestly, any luau you’re planning to attend you should book early, but most people are usually shocked how far out the Old Lahaina Luau books out. Book it as soon as you know your dates (I think they open at the six month window). They also have a waitlist.

Kualoa Ranch UTV Tour (Oahu): Everybody loves Jurassic Park so getting to ride UTVs where they filmed the movies is very popular. The ranch offers a lot of different tours but the UTV tours usually book out a couple of months in advance.

Spa Reservations: If you’re staying at a resort with a spa (or planning on visiting one), don’t wait until you arrive to make your reservations. I’d make them at least a month in advance.

Tee Times: Same for golf, reserve your tee times well in advance.

Dining Reservations: Any “fancy” or resort restaurant is likely to be booked up these days so if you like having a nice dinner every night, make your plans in advance.