I visit Maui pretty frequently (and used to live there) so I’ve stayed in a lot of different hotels and condos on trips (and staycations) plus visited so many more and done a LOT of research.

Like, a LOT of research. I’m kind of a hotel person.

So one of my favorite things is helping people figure out exactly where to stay on Maui.

For starters, here are a few things you need to know:

My tastes (and therefore my recommendations) skew high end to luxury. I’m not really a budget traveler. Although I do like to travel hack my way to a lot of stays.
Hotels on Maui are pretty $$$ (especially since COVID). So if you’re out of touch with current hotel prices (everywhere really, not just Maui), you might be shocked. You’re not going to find something beachfront on Maui for under $400. And really, a lot of places start at about double that. You can definitely find places to stay (even right on the beach) for way less, but you’re going to be looking at a condo. I’ve got a ton of recommendations here, but this post focuses on hotels and resorts.
There are two main areas to stay on Maui: the South side (Kihei and Wailea) and the West side (Kaanapali, Kapalua, and what’s left of Lahaina). I’ll touch on the differences between the two areas briefly in this post as I let you know my specific favorite hotels, but if you want a fully comprehensive breakdown between the two areas, read this post.

Where to Stay in Maui: The Best Hotels in Wailea, Kaanapali & Kapalua

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 Mousin’ Around possible.

My Favorite Hotels in Wailea (I’ve Stayed at Them All ; )

This post has my full breakdown on Wailea vs Kaanapali/Kapalua, but I’ll give you the cliff notes here…while there are things I love about staying on the west side (Kapalua in particular), for my money, I’d pick Wailea every time.

The best resorts on Maui (in Hawaii!) are right here.

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.

***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.

#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

The Hotel Wailea is an outlier, 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.

More Wailea Hotel Comparisons

Besides all of the individual hotel review posts linked above (and here: Four Seasons Maui, Andaz Maui, Fairmont Kea Lani, Wailea Beach Resort ), here are some more in depth comparisons:

Four Seasons vs Andaz Maui

Andaz Maui vs Wailea Beach Resort

My Favorite Hotels in West Maui (Kaanapali & Kapalua)

If you want luxury (I’m talking true 5 star luxury comparable to Wailea), Kapalua is the only place you’ll find it on the west side.

Unlike Kaanapali, Kapalua doesn’t have as much beachfront real estate (a lot of condos have golf course views or they have ocean views but they’re cliffside), but Kapalua’s two luxury resorts have beach access.

Ritz Carlton Kapalua

I’m not going to lie…I’d never been terribly interested in staying in Kapalua because it’s so isolated from the rest of the island and it tends to be a little cloudier/rainier than even Kaanapali just a few miles south, but a few months ago I found a really good point redemption through Marriott Bonvoy so I booked a five night stay.

I loved it so much!

Kapalua has a natural beauty that I think is hard to beat. It’s actually one of the greenest and lushest parts of the island and it makes for some truly beautiful scenery. It’s also a lot quieter and less crowded than Wailea

The pool area is great with three terraced pools plus a large hot tub and a separate pool that’s great for toddlers, but there always seems to be plenty of chairs around no matter what time of day you show up.

One of the best features of this resort is all of the seating areas in the lobby. While at a lot of resorts, the lobby is just a place you move through while you’re coming and going, the lobby area here is a real gathering place. And with views overlooking the whole resort and ocean, it’s a great place to hide away during the inevitable afternoon rain showers.

The other big feature of staying here is the prime access to the Kapalua Coastal Walk. I think this is one of the best hikes/walks on Maui and there’s not a ton of parking to access the trail. But the Ritz Carlton sits at one end of the trail so if you’re a walker, you could do this as a morning walk EVERY MORNING.

One of the major drawbacks to this resort is the beach. I’ve heard people complain that it’s a long walk to the beach, and I wouldn’t say that’s true (it’s 2-5 minutes from the pool) but the beach just isn’t that great. Honestly, if I was making a list of my 5 least favorite beaches on Maui, D.T. Fleming Beach would probably be on it. The water is often rough and the whole time I stayed here there was a lot of run off and it was pretty brown.

The photo below is what it looks like on a “perfect” day.

Kapalua Beach and Napili Beach aren’t far away, but you’d have to take the shuttle and have your own beach gear.

I would probably put the rooms in the “could use improvement” category. They’re just okay. They’re adequate but nothing to give you a wow factor, which honestly isn’t super uncommon at Ritz Carlton properties but should be standard in this price range.

Ritz Carlton is part of Marriott so you can use your Bonvoy points here, which I think is a BIG deal. This place and the Wailea Beach Resort are the two big dog Marriott resorts on Maui. Being able to stay free (or rack up a bunch of points on a cash stay) at a place that often is $1200/night is a big deal. Again, read how I stayed here for free on points here.

You can book the Ritz Carlton Kapalua here.

Montage Kapalua

Quite possibly Maui’s most luxurious resort, the Montage is a sprawling property, but it manages to feel quiet and secluded (like, you might feel like you’re the only ones there).

This 5-star resort only has about 50 rooms so they feel more like private villas. But the sprawling luxurious grounds house every kind of amenity you’d expect at a larger property.

The pool area at the Montage Kapalua is pretty expansive and includes an infinity edge pool looking directly over the ocean. The hotel also has a luxury spa, a high end restaurant, beach bar, and kids club. Resort guests can also take advantage of the excellent golf and tennis facilities in the Kapalua Resort area.

Besides overall being quite a bit more luxurious than the nearby Ritz Carlton (with the price tag to match), the major advantage the Montage has over the Ritz Carlton is the beach. The Montage is a stone’s throw from Kapalua Beach which is one of the best beaches on Maui. They don’t do chair service on the beach, but it’s right there if you want to walk down from the pool for a stroll, a swim, snorkeling, or paddleboarding.

You can book the Montage Kapalua here.

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The Big Three (AKA The Sheraton, The Westin & The Hyatt)

Okay, there are three main resorts on Kaanapali Beach that are my “favorites.” The Westin, Sheraton, and Hyatt Regency. I think they’re good all around resorts that deliver the “Hawaii experience” that the majority of visitors are looking for. Now, these aren’t luxury resorts (Four Seasons, Ritz Carlton, etc), but they’re solid mid range resorts.

Think grand and welcoming properties, efficient and friendly service (but not necessarily personalized), lots of amenities, and lots of people. These are the big box stores of the resort world.

All of these resorts have nice pool areas, multiple restaurants, a spa, beach amenities (chairs, paddleboards, snorkeling rentals, etc.). They’re full fledged resort properties.

They’re also USUALLY all within the same price range. Now, if you’re doing the math for your dates and one of these resorts is significantly cheaper than the other two, that’s probably the one I would go with since they’re all fairly comparable. But I will get into the pros and cons of each specific resort in case there’s something that’s super important to you that one does better than the others.

These three resorts all sit on Ka’anapali Beach in the same general vicinity. The Sheraton is at the far north end in front of Black Rock, the Hyatt is at the far south end and the Westin is in the middle right next to the Whalers Village. They’re all connected by a beachwalk so no matter which one you’re staying at you’re not very far from the others and from everything that Ka’anapali has to offer (including the golf course). So when I mention locations below, just know that I’m being super nit picky since these are all in the same area. On Google maps it says it’s almost a mile to walk the length of Ka’anapali Beach, but it never feels that long when you’re walking the beach pathway.

Westin Maui Resort & Spa

Here’s what I love about the Westin: it’s right smack in the middle of Ka’anapali Beach and next door to Whalers Village so it has the best location of the three if you consider being in the middle of the hubbub the “best.” It’s been EXTENSIVELY renovated over the last couple of years so overall the property is sparkling and probably the most top notch on Ka’anapali Beach, but part of the renovation included the addition of the Hokupa’a Tower.

This new luxury tower not only offers more upscale rooms, but also exclusive access to amenities like the Lanai (a gathering area with a private pool and lounge). It’s the only thing like it in Ka’anapali so if your tastes skew towards luxury, the Westin should for sure be your number 1 pick.

The not so great: well, it’s crowded. All of these resorts tend to be on the crowded side, but because the Westin sits in the middle of the beach and it’s next door to Whalers Village it seems to get more foot traffic than the other two resorts.

You can book the Westin Maui here.

Sheraton Maui

What I love about the Sheraton: It’s down at the end of the beach in front of Black Rock which is a super popular snorkeling spot (it’s good but it’s also super accessible which I think accounts for most of its popularity). The waves tend to be a little calmer down at that end of the beach.

You don’t have to be staying at the Sheraton to use the beach in front, but if you’re staying down at the Hyatt it’s probably a hike to do more than once.

The property feels quieter than the Westin because it’s on the edge. It’s an updated property but it’s also one of the original resorts built in the 1960s and to me it very much has that Elvis/Blue Hawaii vibe.

The not so great: for kids, the pool isn’t quite as entertaining as the Westin or the Hyatt and overall the resort feels a little dated (if you’re not taken in with the vintage vibe).

You can book the Sheraton Maui here.

Hyatt Regency Maui Resort

What I love about the Hyatt: In a word…the penguins. It sounds crazy, but seven African black-footed penguins have taken up residence in the hotel’s atrium lobby and they’re a sight to see! They have feedings every day. It’s pretty magical.

Okay onto the bigger stuff…the Hyatt also underwent a huge renovation in 2020 and it’s pretty spectacular. I think it actually has the best pool area of the three (there’s a grotto swim up bar in addition to a whole kid friendly complex).

It’s a huge resort and there’s a lot of people staying there so it feels crowded even though it doesn’t get the passing foot traffic like the Westin since it’s down at the end of the beach. It also has one of the best luaus in Kaanapali, but you don’t have to be staying there to attend.