Maui’s Most Luxe Resort Has an Infinity Pool with the Best Views in Hawaii

The Four Seasons Maui is the gold standard when it comes to, well…everything. 

In Hawaii, nobody does luxury like the Four Seasons, and since Maui is my particular favorite (and Wailea specifically) I am SO partial to the Four Seasons Maui. 

The resort has the kind of impressive grandeur mixed with relaxed island vibes that can only be described as barefoot luxury. 

After a recent visit to Maui where I spent the first half of the trip hardcore adventuring and exploring, I checked into the Four Seasons Maui for a few days of…vacation.

Here’s everything you need to know about a stay at the Four Seasons Maui…

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Staying at the Four Seasons Maui

Location: Paradise

The Four Seasons is located in the middle of Wailea, one of Hawaii’s most luxurious resort communities on the shores of sun drenched South Maui. 

Sitting right on Wailea Beach, the Four Seasons is the crown jewel of a nice string of high end resorts and everything that comes with “vacationland”…shopping, dining, tennis, golf, snorkeling, beaches, watersports, etc. 

Its prime location on the Wailea Beach Walk means dreamy early morning walks and easy access to beaches, and other resorts for shopping, dining, luaus, and more.

Check pricing & availability at the Four Seasons Maui here.

Arrival: A Vibe

I checked into the Four Seasons on a Monday morning, but the Four Seasons experience really begins before check in. Once I booked, I downloaded the Four Seasons app, and a concierge team member was in communication regarding our stay…mostly to know when we’d be arriving and offering to set up transportation.

Since I was already on island and just changing accommodations, I checked in about 10:30 and was greeted with fresh flower leis, ginger mint lemonade, and chilled lavender towels.

The room wasn’t quite ready, as expected, but the Four Seasons has an “Aloha Suite” with  a showers, lockers, changing rooms, a lounge, a fridge with bottled water, and plenty of charging stations (plus they deliver and pick up your bags from the room so you’ll have access to everything you need). 

In less than 15 minutes after arriving, I was headed to the pool and felt like I was already experiencing the world class service the Four Seasons is famous for.

What a way to start a trip!

Check pricing & availability at the Four Seasons Maui here.

Rooms: Classic Hawaii

It wasn’t long before they texted and let us know our room was ready, and…wow. Since September is a slow time of year, we got upgraded and our room was HUGE. Like, we could have brought an extra 6 people with us. 

Besides the general enormity and luxury of the room, here were some of the highlights: the best bed I’ve ever slept in, a complimentary e-reader loaded with magazines and newspapers, swanky toiletries (seriously everything you could think of including cotton balls and q-tips), a full mini bar, cozy robes and slippers, and a music system in the bathroom. 

The room would’ve been ocean view if it was two floors higher, but as it was the lanai (complete with a couch and chairs) opened up onto a grassy area that we could walk out onto and see out over the whole resort and ocean. 

Overall, I was very impressed with the room, but aesthetically it’s definitely an older, more traditional style than I’ve seen at some of the other resorts in the area.

***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. 

Check pricing & availability at the Four Seasons Maui here.

Service: Unmatched

As I said…in Hawaii, nobody does luxury like the Four Seasons and a BIG part of that is the service. 

It’s hard to explain the difference between the Four Seasons and other high end (and even other luxury) resorts, but here’s an example: 

At a high end resort, you might check in at a kiosk at the pool where they’ll get you a wristband and hand you some towels and then you’re off to pick your spot and set up for the day. And they’ll probably have a waitstaff doing food and drink service that comes by your chairs somewhat frequently to see if you’d like to order something. Not a bad way to spend the day.

But, at a true luxury resort when you walk up to the pool deck, they’ll often remember your name from the day before. They’ll ask you what kind of setup you want (how many chairs, shade, sun, umbrella, location) and show you what’s available because they’re keeping inventory of who is where and if they’ve just left for lunch or if they’ve left for the day. 

Then they’ll follow you to your spot and set up your chairs with covers and lay your towels out and make sure the umbrella is tilted just right and get you water. Which they will then come around and fill up whenever it’s running low. 

And on top of food and beverage service, they’ll have an attendant that brings little treats around every hour like a chilled towel (good heavens my favorite), a pineapple spear, a smoothie sample. 

You get the picture. Both types of resorts are pretty awesome, but there’s a difference in the type of service. 

This scenario…the pool attendants getting you set up at your chairs, adjusting the umbrellas, filling up your water glass when it runs low…that’s the Four Seasons. I’ve seriously never seen anything like it. 

It’s not surprising given their brand and that it’s what they’re known for, but I’m always impressed whether I’m staying on property or just visiting for dinner. They’re a class act. 

Check pricing & availability at the Four Seasons Maui here.

Dining: First Class

Duo is probably my favorite restaurant at the Four Seasons. It’s a high end steak and seafood place right by the main pool deck. It’s also the only restaurant on property that serves breakfast. They do a huge buffet but you can also get things ala carte. 

Ferraro’s is a nice Italian dinner spot (also on the pool deck) but they also do a casual lunch. “Casual lunch” can mean many things, but in Wailea it generally means $30+ per person. But it also means you can enjoy your lunch in your cover up and flip flops with wet hair. The margherita pizza was great and the guava lemonade was fun. Albeit probably not fun enough for the $8 price tag.

If you’re at the pool or beach midday, your best option for lunch (besides poolside service) is the Beachwalk Cafe. They have great grab and go sandwiches as well as drinks, chips, candy, etc. It’s so easy to run down there and grab a sandwich to take back to the pool. They also have yogurt parfaits and breakfast sandwiches in the morning.

Besides just a money saving tip, a big convenience tip (you just don’t always want to be scrounging around for food!) is to grab some groceries/snacks to have in the room. Since rooms have a mini fridge, it’s nice to have some easy grab and go items for breakfast, snacks, or even a light lunch. The nearby Island Gourmet Market at the Shops at Wailea (walkable) has plenty of groceries and prepared items. The prices are going to be higher than what you’re used to at home, but sooooo much cheaper than ordering poolside or sitting down to a full breakfast everyday. Being able to grab a muffin or some pineapple before going down to the pool/beach is pretty nice some mornings.

The lounge in the lobby is also a great place to hangout in the evenings. There’s usually live music and sometimes a hula dancer. Besides great drinks, they have a pretty good variety of pupus (appetizers).

Check pricing & availability at the Four Seasons Maui here.

Amenities: This Is Why You Come

Okay, let’s get to the good stuff…the beach! The pools! The spa!

THE place to be at the Four Seasons Maui is the adults only “Serenity Pool.” The iconic infinity pool with views of Wailea Beach has got to be one of the best resort pools in Hawaii. 

It can get crowded though, but they keep a waitlist and will text you when chairs open up if it’s full when you get there. 

On my stay, I tended to head to the Serenity Pool first thing and then move to the main pool after lunch when I wanted to find a shadier spot. 

Here’s a tip: If you’re visiting during “couples season” (once kids go back to school in the fall) and there aren’t many kids/families at the resort…the adults only pool will be a lot more crowded than the main pool. 

You might get even better service at the main pool and it’s basically adults only too. 

Also, most of the cabanas around the main pool are free and first come, first serve (there are a few ocean facing luxury cabanas that can be reserved for a fee) so that’s a pretty big perk. And (at least in September), we never had a problem finding one midday. 

About Wailea Beach…This is why you came to Hawaii! 

The Four Seasons shares Wailea Beach with the Grand Wailea (the Wailea Beach Resort also has beach access here) so the beach is pretty hopping, but it’s fairly large so it never feels overly crowded. 

The waves aren’t usually wild here (conditions are ALWAYS changing though so pay attention), but they’re usually big enough to make boogie boarding plenty of fun. 

One of my absolute favorite things about staying in Wailea is the beachwalk. This beachfront pathway stretches 1.5 miles from Polo Beach (Fairmont Kea Lani) past Wailea Beach (Four Seasons and Grand Wailea) to Mokapu Beach (Andaz). It’s a beautiful walkway and it has some of the best views you’ll find anywhere!

The Four Seasons is actually one of the only resorts in Wailea with tennis courts (The Wailea Tennis Club is also in the area). So if you’re a tennis player (or just wanting to take a lesson on vacation), the Four Seasons is the place to go.

When I stayed here, they had two artificial turf courts, but they’ve recently converted one court to a pair of pickleball courts and resurfaced it with hard courts. 

More info on the tennis program here including prices and schedule. 

About the spa…I did pay a visit to the spa for a facial during my stay, but unfortunately I have to say it’s probably one of the low points of the resort. I actually found a Groupon deal (that might tell you everything you need to know ; ) and it was okay, but not impressive. The facilities aren’t much to write home about either. 

But a nice perk of staying in Wailea is that amenities at the other resorts are pretty convenient. If you’re looking for THE most fabulous spa experience, that would be next door at the Kilohana Spa at the Grand Wailea.

Side Note: If you’re looking for a rental car for your trip, I LOVE Discount Hawaii Car Rentals. They’re seriously the only company I ever use. They’ll give you the very best prices, you don’t have to reserve with a credit card or pay until you show up, you can cancel and re-book anytime if you find a better rate, and they usually have a special that adds additional drivers for no fee. It’s a no brainer. Click here to check rates for your trip.

Check pricing & availability at the Four Seasons Maui here.

Style: Appropriately Grand

The Four Seasons definitely isn’t stuffy, but it does have a very traditional style instead of the more modern (or even just design-centric) aesthetic that some places have going on. 

To be honest, if I could wave a magic wand and make one big change about the Four Seasons Maui, this would probably be it.

Believe me, there is NOTHING to complain about here, but I personally would love a bit of a “stylish” makeover (especially in the rooms). 

Check pricing & availability at the Four Seasons Maui here.

Value for the Money: Just Don’t Think About It ; )

If looking up the price for a stay at the Four Seasons makes you feel physically ill, there’s really not much I can say about that. 

The top dog resort in Wailea has top dog prices. And honestly, they’ve been pretty off the charts since COVID…I’m still waiting to see how it all stabilizes. 

BUT…Surprisingly, the Four Seasons has more complimentary “extras” than pretty much any other resort in Hawaii. Chalk it up to that five star service. This means that when you’re looking at the price tag of the room, that may include a lot of elements that other resorts “add on” for. So make sure your numbers are all there before deciding if it’s worth it.

The most notable “freebie” at the Four Seasons is that there’s no resort fee. Which is really as it should be because I think resort fees are pretty silly (just build it into the price!), but you’ll be hard pressed to find a resort in Hawaii that doesn’t add on an extra $30-$40 per night for this ambiguous fee.

The Four Seasons also has 64 cabanas that are FREE on a first come, first serve basis. That’s probably way more than most resorts have for a fee. That alone could save you about $500/day.

Check pricing & availability at the Four Seasons Maui here.

Overall: 10/10 WOULD RECOMMEND

WHAT A TRIP.

I seriously cannot recommend the Four Seasons Maui enough. Maui is such a special place to begin with and mixing it with a Four Seasons really just puts it over the top. Unfortunately, I think I’ve now ruined myself for staying anywhere else.

If you’re planning a once in a lifetime trip to Maui to celebrate a honeymoon, anniversary, special occasion, or you simply like staying at “the best,” you should seriously consider staying at the Four Seasons Maui. 

Where to Book

Here’s my final note (and a big favor to ask): If you find my blog and info AT ALL helpful and I’ve convinced you about where to stay on your trip, the absolute best thing you can do to help me out is to click through the links in this post to book your stay. I make a small commission on your bookings and if you’re going to book a hotel anyways, it’s a WIN WIN. Thanks so much!

You can book the Four Seasons Maui here

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.