Four Seasons Maui vs. Montage Kapalua Bay: Which One Fits Your Trip?

If you’re choosing between Maui’s two most luxurious and famous resorts – Montage Kapalua Bay and Four Seasons Resort Maui at Wailea – you already know that both are beautiful. Both are family-friendly. Both have that “you’re being taken care of” feeling. But they’re not interchangeable at all.

I read forums and tried to get a sense of which was better before we went, but I couldn’t decide, so we spent three nights at each one this month.

If you’re choosing between them, here’s the stuff that actually affects your days, your meals, your kid’s mood, and whether you feel like you’re on a retreat or on a classic resort vacation.

The vibe: secluded and peaceful vs. classic resort energy

Montage Kapalua Bay (pictured above) felt almost like it was hiding. Part of that is the location — Kapalua feels quieter, more tucked away, and there aren’t big resorts stacked right next door. Add the fact that Montage is only around 70 residences, and it just naturally feels more peaceful. Less foot traffic, less noise, fewer “events,” more exhale.

Four Seasons Maui is more of that iconic Maui resort experience. You’re in Wailea, which is well-connected and walkable in that “resort-to-resort” way. There’s a little more buzz. Not spring break chaos — just more going on around you. If you like feeling like you’re in the center of things (without it being overwhelming), with easy access to shopping, golf, and a wealth of restaurants, Wailea delivers.

Beach: snorkeling paradise vs. gentle waves you can actually play in

This was the biggest functional difference for us.

Montage / Kapalua Bay is an amazing snorkeling beach. It’s calm, clear, there are lots of turtles, and it’s the kind of water that makes you want to grab a mask and stay out there. But it’s not really the beach I’d pick if the goal is chasing waves or boogie boarding. It’s more “float, snorkel, spot turtles” than “run, jump, ride.” It was perfect for us as we took turns snorkeling and playing in the gentle waves with our toddler. We also saw tons of whale spouts – dozens per day – and had gorgeous views of Lanai and Molokai in the distance, and a full-on sunset view.

Four Seasons / Wailea had crystal clear water and slightly bigger waves — still gentle, but enough to make it fun. Our three-year-old was old enough to go past the small break with us, and it felt like the perfect setup for boogie boarding as kids get a bit bigger. We saw turtles here too, though far fewer, and whales in the distance, but the main draw was simply how good the water felt for actual play. You can catch the sunset from the beach, though it’s a bit angled.

Food: cook-at-home flexibility vs. lots of choices and zero effort (but more cost)

This is perhaps the biggest difference between the two resorts, along with the amount of space you get at the Montage vs. Four Seasons:

Montage is set up for people who are happy cooking sometimes. Every residence has a full kitchen (ours even had a wine fridge, real oven, full fridge, etc.), and honestly that’s part of the point. The tradeoff is that onsite dinner options are limited — think one main dinner restaurant plus in-room dining. It’s not a “pick between four restaurants tonight” kind of resort.

Four Seasons is the opposite experience: more restaurant choices (they have four onsite restaurants), and you can’t cook unless even if you want to as they don’t have kitchens or residences. Being based in Wailea makes it easy to switch things up — you’re near other resorts, so you can wander for a different meal or vibe without it becoming a whole mission.

They have an incredible breakfast buffet, though. Just make sure you book through a Four Seasons Preferred Provider so that it’s included in your stay ($120 daily value!).

Booking with us: perks at no extra cost

If you’re booking either of these, it’s worth doing it with the extra perks through a luxury travel advisor — especially because it doesn’t raise your rate and, at least in our case, we don’t charge any fees.

Montage Kapalua Bay (Virtuoso perks)

Priority for a room upgrade on arrival, when available
Daily $45 breakfast credit for two per bedroom
$150 resort or spa credit per stay
Early check-in and/or late check-out, when available
Preferences communicated to the hotel ahead of arrival

Contact us or browse here (desktop only to pull rates).

Four Seasons Resort Maui at Wailea (Four Seasons Preferred Partner perks)

Daily breakfast for two per bedroom ($120 daily value + kids under 5 eat free)
$100+ Resort credit per stay (amount varies by season)
Priority for room upgrades, when available
Early check-in and/or late check-out, when available
Preferences shared directly with the resort before arrival

Contact us to book.

Rooms and layouts: bigger group friendly vs. classic suite convenience

Montage is a dream for bigger groups because it’s all residences, and they go up to multi-bedroom villas (up to four bedrooms). You get real separation, multiple bedrooms, in-unit laundry, full kitchens, multiple dining areas, grills, in our case 4 bathrooms for our 3-bedroom residence, big lanais… the whole “everyone can be together without being on top of each other” thing.

Four Seasons still worked great for us as a family because of our suite setup — we had an executive suite with a closing door and a pull-out couch, which made evenings and early bedtimes way easier. But this is a room that normally goes for $3500/night, which would be more affordable if booking Montage, and with more space. If you’re traveling with another family, grandparents, or a full crew and want everyone under one roof, Montage has the advantage.

Pools: quiet corners vs. classic resort comfort

Both resorts have surprisingly similar waterslides in terms of size — small, approachable, and perfect for younger kids rather than thrill-seeking teens. The difference is really in how the pool experience feels once you’re there.

At Montage Kapalua Bay, the pool is honestly one of the best we’ve seen anywhere. It was recently revamped, and it shows. The layout is layered and expansive, with multiple levels, tucked-away sections, and little nooks that make it easy to feel like you’ve carved out your own space. Even when other families were around, it rarely felt crowded. You could settle into one corner and almost forget there was anyone else there.

The Four Seasons Maui pool experience feels more traditional – but not in a bad way. It’s polished, social, and very comfortable. One thing we really appreciated was that there are cabanas available that you don’t have to pay extra for, which isn’t always the case at resorts at this level – though they will fill up with people arriving at 7am to snag a spot. While we never made it in time for the prime locations, we were always able to find something. It made it easier to post up for the afternoon without feeling like you had to strategize or commit to a spend. The service was very attentive, which is what FS is known for.

If you love finding a quiet pocket and staying put for hours, Montage’s pool wins. If you like a classic resort pool setup with easy comfort and thoughtful touches like included cabanas, Four Seasons does it really well.

Service: both great, but Four Seasons does that Four Seasons thing

The service at both was excellent. You’ll truly want for nothing at either spot.

Montage felt warm and calm and attentive — and the twice-daily housekeeping in a full residence was honestly kind of wild (they even did the dishes we left in the sink). They even brought a full cake for my partner’s birthday, and left such thoughtful touches in the room for our toddler as well. They’re partnered with UPPAbaby, so they have strollers and cribs onsite of the highest quality.

And Four Seasons is legendary for a reason. It had that signature smoothness where everything is immaculate, everything runs on time, and you’re never thinking about logistics because someone already handled it. Housekeeping knew our names. Valet was genuinely helpful when we were figuring out where to go for the day. It’s what Four Seasons is known for across properties — that quiet competence that makes you feel like you can actually relax.

Also: Four Seasons has a free photo service that I wish more resorts did. It’s a quick ~10-minute session where a photographer takes photos using your phone, so you get them immediately without a gallery, waiting, or awkward upsell.

So… which one wins?

It depends on what kind of trip you’re trying to have. Here’s how I’d call it.

Pick Montage Kapalua Bay (full review here) if you want:

Maximum peace and quiet
A secluded part of Maui without big resorts right next door
A snorkeling-first beach (turtles, calm water)
A place that works beautifully for bigger groups (multi-bedroom residences)
The option to cook and spread out like you actually live there

While this is very much a 5-star luxury resort, the value/amount of space you get for your money at Montage will be higher. For the price of an executive suite at the Four Seasons, you can get a 2-3-bedroom villa at the Montage with a full kitchen and beautiful view.

Contact us or browse here (desktop only to pull rates).

Pick Four Seasons Maui at Wailea (full review here) if you want:

A beach where you can play in gentle waves (and boogie board as kids get bigger)
More restaurant choices and zero desire to cook
The convenience of Wailea (walkable resort area, near golf courses, easy to hop around)
A location that’s closer to the airport
That signature Four Seasons service — names remembered, everything seamless — plus the free sunset photo session on your phone

Contact us to book.

If I had to sum it up in one line: Montage is the calm, residential reset. Four Seasons is the classic Maui resort vacation with legendary service and easier food variety.

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