*This post was updated in November 2024.

I visit Hawaii 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.

It’s hard to complain much about any hotel in Hawaii (it’s paradise!), but some hotels definitely make more of an impression than others.

So I’ve rounded up my FAVORITE hotels in Hawaii, plus the ones that are on my wish list.

But first, 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 in Hawaii are pretty $$$ (especially since COVID). So if you’re out of touch with current hotel prices (everywhere really, not just Hawaii), you might be shocked. You’re probably not going to find something beachfront (outside of Waikiki) for under $300. 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.

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.

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

My Favorite Maui Hotels

Four Seasons Maui

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.

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.

Read my full review of the Four Seasons here.

You can book the Four Seasons Maui here.

Andaz Maui

The Andaz Maui is Hyatt’s most coveted resort in Hawaii and holds its weight in a resort area stacked with some of Hawaii’s finest luxury resorts.

The resort’s modern aesthetic, laid back aloha vibes, tiered ocean facing infinity pools, and a somewhat secluded spot on one of Maui’s best beaches make the Andaz Maui one of my top picks for a luxe getaway.

The Andaz feels a bit more hidden away than some of the other big resorts in Wailea. And 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 is also one of my overall favorites. 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.

Read my full review of the Andaz here.

You can book the Andaz here.

Wailea Beach Resort

I’m always on the hunt for the perfect beach resort and Marriott Bonvoy is my hotel loyalty program of choice… so when I find a place that checks both boxes, I am ALL OVER IT.

The Wailea Beach Resort on Maui is one of the most popular Marriott properties in the world right now (evidenced by how many people choose to redeem a good chunk of their loyalty rewards points here), and it’s easy to see why.

Aesthetically, the Wailea Beach Resort has a modern vibe with a welcoming, open air lobby and plenty of public spaces that invite guests take advantage of the beautiful setting.

And there’s something for everyone…some of the island’s best waterslides for the kids…and a truly impressive oceanfront infinity pool for the adults.

I can’t wait to make it back for another stay to check out the newly opened Olakino Wellness Pool Experience (like a spa day at a luxury pool with a view of the ocean!)

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.

Fairmont Kea Lani

The Fairmont Kea Lani is a classic Hawaii beach resort offering everything you could ever want on vacation, but I think what separates it from a lot of the competition are the rooms.

The Fairmont Kea Lani is Hawaii’s only oceanfront all-suite and villa resort which makes it a perfect option for families or couples who want more room to spread out. And pricewise, it’s usually on the lower end of the surrounding resorts in Wailea. So it’s a great VALUE.

And on top of all of that, they just finished a resort wide renovation in 2023 and the new room interiors are probably…the best on Maui.

Read my full review of the Fairmont Kea Lani here.

You can book the Fairmont Kea Lani here.

Ritz Carlton Kapalua

As one of the greenest and lushest parts of the island, Kapalua has a natural beauty that I think is hard to beat. And the Ritz Carlton has a prime location in this quiet and serene paradise.

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.

My other favorite 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.

Read my full review of the Ritz Carlton Kapalua here.

You can book the Ritz Carlton Kapalua here.

Grand Wailea

The Grand Wailea is probably the most famous resort on Maui (maybe in all of Hawaii) and partly that’s because of its size and “grandeur” and partly because it’s been around so long that generations of families have memories here and really help keep the buzz going.

I’ll be honest, if it’s an adults only trip, the Grand Wailea isn’t on my list. BUT…if you have kids, the Grand Wailea is THE place to stay.

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.

You can book the Grand Wailea here.

Maui Hotels on My Wish List

Montage Kapalua: They say if anything compares to the level of luxury at the Four Seasons, it’s the Montage Kapalua. I’ve strolled around the grounds and it looks pretty great. It’s on my list. For when I can pry myself away from Wailea ; )

Hotel Wailea: Hawaii’s only Relais & Chateau property is tucked away in the hills above Wailea. It’s adults only and such a cool little hideaway (their restaurant is one of my favorites on the island), but I haven’t pulled the trigger yet since it’s not on the beach. Soon though!

Westin Maui Resort (Hokupa’a Tower): As part of a huge renovation, the Westin added a new luxury tower that 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 (and I do love Ka’anapali) so I definitely want to check it out. It’s just not super high on my list since it’s in the same price range as luxury resorts in Wailea.

Hana Maui Resort: I’ve only ever done Hana as a day trip, but someday I want to spend a few days off the grid at the Hana Maui Resort. I’ve been waiting for the promised “top to bottom” renovation since Hyatt took over though because reviews on the standard level rooms aren’t super stellar.

My Favorite Oahu Hotels

Disney’s Aulani Resort

Disney’s Aulani Resort is a one of a kind vacation experience where the magic of Disney meets the rich culture and breathtaking beauty of the Hawaiian Islands. And really, it’s the perfect blend.

Whether you’re a “Disney person” or not, you can’t help but be impressed with how Disney’s imaginative storytelling and dedication to details mingles with the spirit of aloha and Hawaii’s incredible culture to deliver…basically the perfect vacation destination.

There’s a lot to love about Aulani, but its standout feature is its incredible water complex, the Waikolohe Valley. This oasis is home to swimming pools, whirlpool spas, a lazy river, splash pads and water playgrounds, and thrilling water slides, all designed to mimic the Hawaiian landscape, from its volcanic formations to its lush vegetation. And Rainbow Reef, a snorkeling lagoon filled with native Hawaiian fish, offers guests a safe and accessible glimpse into the underwater world of the islands.

Combine it with a family friendly beach, an endless amount of activities around the resort, and Disney’s famous top notch customer service, and this place is a clear winner.

Read my full review of Disney’s Aulani Resort here.

You can book Disney’s Aulani Resort here.

The Laylow

I love the grand resorts of Waikiki as much as the next girl, but sometimes you don’t need the full resort experience.

The Laylow is definitely my new go to Waikiki hotel. I don’t love paying the big $$$ for the nice hotels on the beach when I’m usually a bit more on the go then when I stay on Maui, Kauai, or even other parts of Oahu, but the Laylow still feels like more of a destination hotel than most budget friendly hotels in Waikiki.

The Laylow is a high end city hotel with the vintage Hawaiiana charm everybody dreams of.

They’ve really leaned hard into the vibe. In some ways, I think of the Laylow as the Royal Hawaiian’s (little) sister property.

It’s big on style, and has an overall “nice” feeling, while staying light on amenities and services and making the perfect basecamp.

Read my full review of the Laylow here.

You can book The Laylow here.

Oahu Hotels on My Wish List

Ritz Carlton Turtle Bay: It’s been on my list to stay at Turtle Bay on Oahu’s north shore for years, but when it joined the Ritz Carlton brand earlier this year, it shot to the very top. The location is a gem (resort options outside of Waikiki on Oahu are limited) and it looks soooo nice.

Four Seasons Ko Olina: I always stay next door at Disney’s Aulani Resort, but eventually I want to stay a few days at it’s much more luxurious neighbor.

Royal Hawaiian (Mailani Tower): I LOVE a historic pink hotel and nothing is more iconic than the Royal Hawaiian. The hotel is so dreamy, but it’s on my bucket list to stay in the newer Mailani Tower with its updated rooms and sweeping views of Waikiki and Diamond Head.

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.

My Favorite Big Island Hotels

Mauna Kea Beach Hotel

Opened in 1965, Laurance Rockefeller’s Mauna Kea Beach Hotel was the first resort development on the Big Island and almost 60 years later it’s still delivering the kind of vintage Hawaiian vibes that are getting hard to find.

Honestly, I’m pretty obsessed with this place. The beach is STUNNING. I think it’s the best hotel beach in Hawaii. Maybe just the best beach in general.

There’s a viewing platform where you can watch the manta rays every night plus one of the best tennis clubs in the world.

The Mauna Kea Beach Hotel is currently undergoing some pretty extensive renovations (expected to last through 2025), but it’s going to be EVEN MORE FABULOUS then.

Read more about the Mauna Kea Beach Hotel here.

You can book the Mauna Kea Beach Hotel here.

Fairmont Orchid

I think the Fairmont resorts in Hawaii sometimes get lost among the dazzling lineup of the competition, but the Fairmont Orchid on the Big Island is a SOLID beach resort.

The Fairmont Orchid is a relaxed five star resort situated on 32 oceanfront acres about 20 miles north of the Kona airport. With plenty of amenities including a pristine pool complex, golf, tennis, a spa, a sandy beach with good snorkeling, resident sea turtles, a handful of restaurants, and numerous cultural activities, it’s possible to be “busy” just taking advantage of everything the resort has to offer.

The Fairmont has everything you could want in a beach resort…plenty of dining, golf, spa, tennis, etc. But it’s often a bit less expensive than other comparable resorts in the area.

I really love the way the pool area is situated here. It’s pretty large for the size of the resort with plenty of chairs (and cabanas and shade loungers) scattered around. The way it sits on the property, it feels wide open to the ocean which is something I really like.

Read more about the Fairmont Orchid here.

You can book the Fairmont Orchid here.

**Just a quick footnote here since it’s sooooo popular….yes, I’ve stayed at the Hilton Waikoloa Village and didn’t love it. I found it to be inconveniently large, pretty outdated, understaffed, and just generally nowhere near as nice as other options in a similar price range.

Big Island Resorts on My Wish List

Mauna Lani Resort: One of the chicest places to stay on the Big Island, this place looks amazing after a top to bottom renovation on an older property.

Four Seasons Hualalai: This is pretty much the ultimate Hawaii luxury beach resort. I’m dying to stay here and the salt water lagoon pool looks INCREDIBLE.

Pacific 19: This cute boutique hotel in downtown Kona looks like a great budget friendly spot to set up basecamp.

SCP Hilo: An eco conscious boutique hotel with the perfect location for exploring the jungle-y side of the island.

Volcano House: My dream is to stay at Volcano House in the National Park when there’s lava in the crater!

My Favorite Kauai Hotels

Grand Hyatt Kauai

The Grand Hyatt Kauai is one of the largest resorts on the island and has everything you could ever want in a mega beach resort. The combination of over the top “grand” architecture, impressive grounds and pools, and activities and offerings everywhere you turn make it one of the best resorts on Kauai for families.

From the minute you pull onto the property, you’re going to be impressed. It’s just one of those kinds of places where you never quite get over the scale. It doesn’t have “Grand” in the name for nothing.

The lobby is a huge open air affair with distant ocean views. So much marble. So many parrots and orchids.

It’s so lush and well manicured, and everywhere you turn there’s a magnificent view.

Kauai Resorts on My Wish List

1 Hotel Hanalei Bay: I stayed at this resort when it was still the St Regis and I can’t wait to return to see the impressive renovations. Everything about this place looks stunning (and kind of dream-like) and I can honestly say that of all the places I’ve stayed in Hawaii, this spot wins hands down as the best setting.

Koa Kea Hotel: I love a small, laid back boutique hotel and this one on Poipu Beach is pretty perfect. I’ve had dinner here and walked around the grounds, and it’s at the top of my list for a place to stay on Kauai’s south side.

How I Booked 3 FREE Trip to Hawaii (Including Airfare & Hotels) in the Last Year

I’ve been on THREE trips to Hawaii in the last year with free flights AND free hotels ALL booked using points and miles.

That’s:

One trip to Maui staying at the super swanky Wailea Beach Resort and doing my favorites like sunrise at Haleakala, the Road to Hana, and soooo much beach time.

One trip to the Big Island staying at the Mauna Kea Beach Hotel to visit Hawaii Volcanoes National Park, tour a Kona coffee farm, and see the manta rays after dark.

And one trip to Maui staying at the Ritz Carlton Kapalua to explore the west side beaches, drive the Kahekili Highway, and do a day trip to Lanai.

WITH FLIGHTS FOR TWO PEOPLE.

Some people call it “travel hacking,” but basically…it’s using credit card points & mile systems to cover travel experiences, usually in a more luxurious way than you would normally if you were paying cash.

I’m certainly no expert in this industry, and I’m sure there are people who do this WAY better than me (and on a bigger scale), but I do travel to Hawaii a lot and I’ve saved a LOT of money using points and miles. So I’m going to tell you how I do it ; )

First of all, a BIG Disclaimer: You should NEVER go into credit card debt to do this. And you should never use this to justify spending more money on things than you normally would because you’ll “get points.”

Also, let’s be clear. Stringing together free stays and amazing deals isn’t as simple as applying for one credit card and getting a free trip. It usually involves a little more strategy and synchronization (and sometimes just time to accrue points).

But here’s how to start:

Pick an Airline

I like Southwest and they’re the only airline I fly to Hawaii anymore. They’ve also got BY FAR the easiest credit card point system to use plus bags are free I think they have the most flexible rebooking/cancellation policy.

I have this Southwest Premier Rapid Rewards Visa card through Chase. The current sign up offer is 50,000 points. Depending on where you live and fly from, that’s at least one completely FREE ticket to Hawaii and it could be two depending on the time of year (or more if you catch a crazy sale).

The card also gives you:

2 Early Bird Check-Ins per year (super nice when you’re going to Hawaii and the perfect seat is really important)

6000 anniversary points

3x points on Southwest purchases (more points for your next flight)

If you’re new to the “travel hacking” game, I think this is a REALLY good place to start. You’ll get some free flights right away and honestly, I feel like Southwest points rack up sooooo fast when you’re using the card for your everyday purchases.

Again, use >> this link << to get 50K bonus points when you sign up.

But my FAVORITE Southwest points feature is the Companion Pass. If you rack up enough points in a calendar year (through credit card spending and flights flown), you get a Companion Pass. For the entire year, every time you fly, you get to take somebody with you FOR FREE (whether you pay cash or book with points).

The Companion Pass is good for the rest of the year when you qualify plus the entire next year (for example: if you qualify in October, you get the Companion Pass for the rest of that year plus the entire next year)

So once you qualify for a Companion Pass, your points actually end up going twice as far.

It’s too good to pass up. Details >> here <<

Later in this post I’ll get into logistics about picking the best airline that makes sense for YOU to fly (based on where you’re flying from) and I’ll layout options with Southwest, American, United, Delta, Hawaiian, and Alaska.

So keep reading!

Pick a Hotel

Hotels and resorts are my FAVORITE thing to use credit card points on because there’s such a spectrum of what you could save. Flights cost what they cost, but using points on a luxury hotel could save you up to $1500 PER NIGHT.

My go to is Marriott. They have by far the most options available of any of the major hotel chains plus they’ve got a ton of luxury and boutique options (which are my favorite).

This Marriott Bonvoy Boundless card through Chase is probably my most used credit card.

As soon as you sign up for this card (and meet the minimum spend requirement) you get 3 FREE nights to use anywhere you want! The free nights attached to this card are good for hotels worth up to 50K points per night (plus you can add 15K points to each of those certificates) meaning you can book three nights at a hotel that’s valued at up to 65K points per night. There are quite a few hotels in Hawaii that will fall into that category (even more if you go during shoulder season – spring or fall).

Again, use >>this link<< to get 3 FREE nights when you sign up for this card.

But I have a “go big or go home” philosophy when it comes to travel, so I like to DOUBLE DIP on Marriott Bonvoy rewards with the Marriott Bonvoy Business Amex.

If you’re self-employed, a freelancer or contractor, a gig economy worker, if you own rental properties, etc…you qualify for a business card. (And you don’t need to be registered as an LLC or corporation. You can apply as a sole proprietorship with just your social security number.)

This card comes with three free 50K nights (the same as my Marriott Bonvoy Boundless through Chase) so right out of the gate, that’s SIX FREE NIGHTS.

Plus having both really gives you a jump on hitting an “elite status level” where you get perks like free breakfast, room upgrades, late check out, etc.

AND with each of these cards…every year on the anniversary of the date you opened your card, you get a free 35K/night free night certificate. I just used a couple of these to stay at the new AC Hotel Wailea!

Later in this post I’ll get into the logistics of which Marriott properties on which islands will give you the best options for using free nights plus which properties are most “aspirational” (AKA which ones I would save up a bunch of points to spend on).

Two Free Nights at the Grand Wailea on Maui

Yes, yes, yes, I’m pretty loyal to Marriott. BUT here’s a “quick hit” that’s good to know about…

Maui’s flagship luxury resort, The Grand Wailea, is a Waldorf Astoria hotel which is owned by Hilton. If you scout around a bit, you can usually find it available for as low as 110K points per night. Right now, the sign up bonus on this Hilton Honors (Amex) is 155K.

And one of the Hilton loyalty program’s stand out features (to me) is that members can transfer points to one another without a limit (Marriott caps the number of points you can transfer to someone at 100K per year).

If your travel partner (husband, wife, daughter, friend, etc) also signs up for the card and gets the bonus, one of you can transfer your points to the other and you’ll have enough points total to book 2-3 nights!

That’s probably not going to be your whole trip, but you can either pay cash for the remaining nights (a major way to lessen the bill), or use your free nights at the end of your trip (maybe you’re staying in an affordable condo) as a big splurge.

Again, use >>this link<< to get your 155K point sign up bonus when you sign up for this card.

More about Flying to Hawaii ON POINTS

Okay, now that you know about my favorite airlines for points, here’s what you need to know LOGISTICALLY about flying to Hawaii:

Flying Southwest Airlines to Hawaii

Here’s what Southwest flights to Hawaii look like.

You can fly direct to Hawaii on Southwest from:

Las Vegas (LAS) to Maui (OGG), Oahu (HNL), Kauai (LIH), Big Island (KOA)

Oakland (OAK) to Maui (OGG), Oahu (HNL), Kauai (LIH), Big Island (KOA)

Phoenix (PHX) to Maui (OGG) and Oahu (HNL)

Sacramento (SMF) to Oahu (HNL)

San Jose (SJC) to Oahu (HNL)

Los Angeles (LAX) to Oahu (HNL)

Long Beach (LGB) to Oahu (HNL)

San Diego (SAN) to Oahu (HNL)

If you live in one of those cities, you are GOLDEN. You’ll be able to find flights fairly cheap (and low miles) and it’s an easy 4-6 hour flight.

If you do not live in one of those cities (hi, it’s me), you’ll need to do a little research into which (if any) you can fly directly from your city to.

For example, flying from Tulsa, OK, I can get direct flights on Southwest daily to Las Vegas and Phoenix, making those options for me to get to Hawaii (Southwest won’t sell you a through ticket with more than one connection).

Now, the flight times have to line up so you’ll be able to do it all in one day, but I can usually make something work even if it’s just on certain days of the week.

Maybe you noticed that from Las Vegas you can fly to all four of the main Hawaiian Islands, and that’s not by accident.

First of all, Las Vegas is a wildly popular destination with Hawaiians so there’s always demand for those flights.

Second, most mid-sized cities in the US have direct flights to Las Vegas making it the perfect “hub” for Southwest to use for people who don’t live in one of the cities with a direct flight and need to make a connection.

Live in Minneapolis, Dallas, Denver, Memphis, Albuquerque, Charlotte, Chicago, Columbus, Pittsburgh, etc? You can probably get a direct flight to Vegas which opens up Hawaii to you.

So flying to Hawaii from Las Vegas, Oakland, Phoenix, Sacramento, San Jose, Los Angeles, Long Beach, or San Diego will generally be fewer points (and a cheaper cash price) than if you have to make a connection, but you’ve got options. And that’s not even taking into account a sale.

PLUS…when Southwest entered the Hawaii market, they also added a TON of interisland flights so even if you can only get to Oahu from the mainland, you can easily island hop once you get there.

Flying United Airlines to Hawaii

If you’re flying out of any of these cities, United is a great option for Hawaii:

Chicago (ORD) has flights to Oahu (HNL), Kona-Big Island (KOA), and Maui (OGG)

Denver (DEN) has flights to Oahu (HNL), Kauai (LIH), Kona-Big Island (KOA), and Maui (OGG)

Houston (IAH) has flights to Oahu (HNL)

Los Angeles (LAX) has flights to Oahu (HNL), Hilo-Big Island (ITO), Kona-Big Island (KOA), Kauai (LIH), and Maui (OGG)

New York Newark (EWR) has flights to Oahu (HNL) and Maui (OGG)

Orange County (SNA) has flights to Oahu (HNL)

San Francisco (SFO) has flights to Oahu (HNL), Kauai (LIH), Kona-Big Island (KOA), and Maui (OGG)

Washington Dulles (IAD) has flights to Oahu (HNL)

I’m currently working on the United Explorer MileagePlus (Chase) sign up bonus for an upcoming trip to Tokyo, but one of the things I’m most excited about is that if you book a cash ticket with United, you can use your miles to upgrade your economy seat to business class.

I don’t think that’s a big deal if you’re flying to Hawaii from the west coast, but if you’re flying from the east coast (even Houston or Chicago) it’s sooooo much nicer to fly in business or first class.

If you use >>this link<< to sign up for the card, you’ll get a 50K point bonus which could be enough to book a free economy ticket to Hawaii OR upgrade your economy ticket to first class.

The other reason I love this card is because United is one of Chase’s travel partners and my Chase Sapphire Reserve card is my go to travel card in general. So I can transfer my Chase Ultimate Rewards points to United to book directly if there’s a flight that works best for me.

And United is also in a bigger airline alliance so you have a lot of options to use your points on other airlines if you travel internationally.

Grab that United 50K bonus here.

Flying American Airlines to Hawaii

If you’re flying out of any of these cities, American Airlines could be a good option for Hawaii:

Dallas (DFW) has flights to Maui (OGG) and Oahu (HNL). These two routes are AA’s “Flagship” Hawaii routes meaning they fly a widebody aircraft more commonly seen on international flights. You’ll get a full meal plus the option for premium economy seating and lie flat seats in business class. These flights are usually more $$$ even in economy.

The rest of these routes are just standard domestic flights:

Los Angeles (LAX) has flights to Oahu (HNL), Kauai (LIH), Kona-Big Island (KOA), and Maui (OGG).

Phoenix (PHX) has flights to Oahu (HNL), Kauai (LIH), Kona-Big Island (KOA), and Maui (OGG).

*AA used to fly some routes to Hawaii from Chicago and Charlotte, but those aren’t currently offered.

Flying Delta Airlines to Hawaii

If you’re flying out of any of these cities, Delta could be a good option for Hawaii:

Atlanta (ATL) has flights to Oahu (HNL) and Maui (OGG).

Detroit (DTW) has flights to Oahu (HNL).

Los Angeles (LAX) has flights to Oahu (HNL), Kauai (LIH), Kona-Big Island (KOA), and Maui (OGG).

Minneapolis (MSP) has flights to Oahu (HNL).

New York (EWR) has flights to Oahu (HNL).

Salt Lake City (SLC) has flights to Oahu (HNL).

Seattle (SEA) has flights to Oahu (HNL).

Delta also offers interisland flights so you can connect to another island through Honolulu.

Flying Hawaiian Airlines to Hawaii

If you’re flying out of any of these cities, Hawaiian Airlines could be a GREAT option for Hawaii (get those aloha vibes going before you even get there ; )

Austin (AUS)

Boston (BOS)

Las Vegas (LAS)

Long Beach (LGB)

Los Angeles (LAX)

New York (JFK)

Oakland (OAK)

Ontario, California (ONT)

Phoenix (PHX)

Portland (PDX)

Sacramento (SMF)

Salt Lake City (SLC)

San Diego (SAN)

San Francisco (SFO)

San Jose (SJC)

Seattle (SEA)

Hawaiian Airlines also offers an extensive network of interisland flights.

Flying Alaska Airlines to Hawaii

This west coast based budget carrier isn’t something that’s ever on my radar (since I fly from the middle of the country), but if you’re flying out of one of these cities, they’re usually very competitively priced.

Anchorage, Alaska (ANC)

Portland (PDX)

Los Angeles (LAX)

San Diego (SAN)

Seattle (SEA)

San Francisco (SFO)

San Jose (SJC)

Always Book Directly with the Airline

Whichever airline you choose, be sure to follow the cardinal rule of air travel. ALWAYS BOOK DIRECT. Under no circumstances should you ever book airfare through a third party company like Expedia, Travelocity, and I hate to say it but even Costco. Air travel is WILD. Wildly undependable.

Flights get delayed, they get canceled, plans get derailed. And when you’ve booked through a third party, you can’t deal with the airline directly. You can literally be in the airport at the gate and depending on what the problem is (flight canceled, flight delayed and you’re going to miss your connection, etc) the gate agent may not be able to help you.

You haven’t known frustration until you’re literally standing in front of a human that handles flight changes for the airline and they can’t help you because you have to call Expedia and be on hold with them for 6 hours instead. When you book with a third party, THEY hold the reservation, not you.

Here’s the other thing…these booking sites hardly ever have prices any cheaper than the actual airline anyways. Do your research using Expedia or whoever you like to shop and then go directly to the airline to book.

More about Using Marriott Points in Hawaii

Besides the traditional Marriott marquis hotels, Marriott’s brands in Hawaii also include Sheraton, Westin, Ritz Carlton, Courtyard, Residence Inn, Marriott Vacation Club, and the Luxury Collection & Autograph Collection (collections of boutique hotels like the Royal Hawaiian, Moana Surfrider, Mauna Kea Beach Hotel, and the Laylow – these are some of my favorites ; )

So there are a LOT of great hotel choices in Hawaii under the Marriott umbrella – whether you’re looking for a once in a lifetime destination resort, a boutique hotel with fun vibes, or a good bang for your buck hotel.

Hawaii Hotels to Use 50K Free Night Certificates

In Hawaii (depending on dates), that could work at hotels like:

Oahu: The Laylow, Royal Hawaiian, Moana Surfrider, Courtyard Waikiki Beach, Sheraton Princess Kaiulani, Waikiki Beach Marriott, Renaissance Honolulu Hotel, AC Hotel Honolulu, Residence Inn Kapolei, and Courtyard North Shore.

Maui: Sheraton Maui Resort, Westin Maui Resort, AC Hotel Wailea, Courtyard Kahului (in August 2024 the Wailea Beach Resort has redemptions for 55K/night!!)

Kauai: Sheraton Kauai Coconut Beach Resort, Sheraton Kauai Resort

Big Island: Courtyard King Kamehameha’s Kona Beach Hotel, Waikoloa Beach Marriott

But I’ve saved my favorite thing about using Bonvoy points to book Marriott hotels for LAST:

When you book four nights using points, you get a FIFTH NIGHT FREE. So after I use my free night certificates (that have max point values like 50K or 35K per night), I only use my Marriott points for “big” stays where I have enough points to book four nights and get the fifth free. It’s by far the best way to max out the value on your points.

Side note: You cannot combine free night certificates with points to take advantage of the fifth night free promo.

Last year, I cashed in 325K points to stay for 5 nights at the Mauna Kea Beach Hotel on the Big Island. And I’m getting ready to stay at the Ritz Carlton Kapalua for 5 nights for 330K points.

And obviously, if you’re not staying at premium luxury properties, you can get stays for a LOT less. Or stay a lot longer ; )

I mentioned a list of hotels above that are good places to get the best “bang for your buck” on points and use free night certificates above, but if you’re like me, and you have a “bucket list” of great hotels, here’s also a list of the top aspirational Marriott properties in Hawaii (places that are worth hoarding your points for a big splurge):

Wailea Beach Resort (Maui)

Ritz Carlton Kapalua (Maui)

Koloa Landing Resort (Kauai)

Mauna Kea Beach Hotel (Big Island)

Royal Hawaiian (Oahu)

Moana Surfrider (Oahu)

Turtle Bay Resort (Oahu) ***This hotel JUST joined the Ritz Carlton brand earlier this year!!

Hawaii FAQs

When is the best time to go to Hawaii?

I’ve got good news for you…there’s no BAD time to go to Hawaii ; )

But depending on what you’re after (low crowds, best weather, low prices, WHALES), then some times are definitely better than others.

As far as weather goes, Hawaii is pretty temperate year round (the air and water temp only varies a few degrees), but their seasons technically match ours on the US mainland. Our summer is their summer and our winter is their winter. The biggest thing weather wise is that it rains more during the winter months.

But if you’re staying in the resort areas (Waikiki and Ko Olina on Oahu, Wailea/Kihei and Lahaina/Kaanapali on Maui, Kona and Kohala on the Big Island, and Poipu on Kauai) you’re going to be pretty good on the sunshine year round.

If you’re planning your trip with the main goal of seeing humpback whales…make it February, and make it Maui.

As far as crowds go…when kids are out of school is peak season. The summer months and winter holidays will be the most crowded (and expensive).

The best times to go to Hawaii in terms of low crowds and therefore low(er) prices are during shoulder season in the spring and fall.

I’ve been to Hawaii pretty much all times of the year and I’m constantly monitoring prices on flights and hotels and I consistently find mid April through May and mid August through mid October to be the cheapest time of year to go to Hawaii.

But my personal FAVORITE time to go to Hawaii is…February!

February is not necessarily the cheapest or the least crowded (it’s also not the most!), but there is NOTHING more luxurious than escaping the long, cold, dark winter where I live for a trip to Hawaii. I will pay a little bit more as a “winter tax” and while visiting Hawaii anytime is a treat, visiting Hawaii during the winter is my ultimate treat.

Read more about the best times to visit Hawaii here >> Best Time to Visit Hawaii

Which Island is best?

If you want gorgeous beaches, aloha vibes, water and cultural activities, good food, great hotels, and an all around amazing vacation…I can plan you the PERFECT Hawaiian vacation to ANY of the main four islands (Oahu, Maui, Kauai, Big Island). Seriously, anyone that tells you that a specific island is the best “hands down” is just biased. They’re all spectacular.

If you’re not already swayed to one island over another, some things that I would consider…

Are there direct flights to a certain island from where you live? Sometimes the easiest logistics will sway my vacation planning.

Are there specific activities that you’re interested in or sites you want to see that are unique to a certain island? Always wanted to see Waikiki and Pearl Harbor? Head to Oahu. Hawaii Volcanoes National Park and swimming with manta rays? The Big Island. The Road to Hana and Haleakala National Park? Maui. Those jagged green Jurassic Park mountains? Kauai. While all of the islands have some version of what you’ll expect from a Hawaiian vacation, there are a handful of unique experiences on each island.

Start with these posts about things you can ONLY do on each island: Maui, Big Island Kauai, Oahu.

If we’re making the vaguest of generalizations, people usually say that Oahu is city and has the most things to do. Kauai is country and is the most undeveloped. Maui is the best overall island. And the Big Island is the most undiscovered.

I can (and do) argue all of those points in this post if you want to read more about picking the best island for YOU.

How many days on Maui? Or Kauai? Or Oahu?

Well, you’ve only got however many days you’ve got, but if you’re wanting the best overall vacation, I wouldn’t suggest less than one week (probably 6 full days, but you could do a lot in 5 full days too) on any one island.

If you’re short on time (doing a quick long weekend getaway from the west coast), you can still have a great trip just as long as your expectations are more about resting and relaxing.

But in general, if you’re wanting to explore the island and still feel like you’ve had a relaxing vacation, you’ll want at least 6 full days. I also don’t recommend splitting up a one week vacation between two different islands. Just stick to one and really experience it.

The exception to this is if you’re going to spend a week on one island and add on a few days on a different island because there’s something really specific that you want to see.

Which airport to fly into?

These days, the four main islands are all easily accessible from the mainland US (or a quick layover in Honolulu). Here’s a list of each island’s major city and airport code:

Oahu: Honolulu (HNL)

Maui: Kahului (OGG)

Kauai: Lihue (LIH)

Big Island: Kona (KOA) or Hilo (ITO)

What’s the best airline to fly?

The short answer…it’s the airline that offers the best flight options from YOUR home airport.

For me, that’s usually Southwest (I’ve written a full post about why they’re my airline of choice here).

For you, that could be American, United, Delta, Hawaiian, or Alaska Airlines.

This post has all my best info about flying to Hawaii.

Do I need a rental car?

In a word, yes.

Hawaii is not an all-inclusive destination where you’ll arrive by shuttle and never leave your resort (I mean you could do that…but it’s pretty expensive just to get to Hawaii so most people want to actually see Hawaii. If you want a cheaper resort only vacation, just go to Mexico).

The islands are pretty large so unless you’re just going a few miles, taking Ubers and Lyfts isn’t really feasible (you could be talking $100 one way to go to another part of the island). Also, Oahu is the only island that has a decent bus system.

So you’ll most definitely want a rental car for your stay even if you’re staying in a resort area. I always book through 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.

Where should I stay?

My favorite question!!

I am a hotel PERSON and I’ve stayed at a LOT of hotels in Hawaii.

On Maui, the first thing you’ll have to decide is which part of the island to stay on. Most visitors either stay on the South Side (Wailea and Kihei) or the West Side (Kaanapali and Kapalua). Both have beautiful beaches, plenty of restaurants, and all of the vacation amenities you could want. I’ve got a full comparison/breakdown of the two areas here >> Wailea vs Kaanapali

Personally…I prefer to stay in Wailea. It’s a bit nicer, has everything you could ever want right there (plus soooo many restaurants nearby in Kihei), AND it’s more conveniently located for exploring the rest of the island.

As far as specific hotels, the Four Seasons Maui is the go to if you’re looking for luxury. But I’m becoming partial to the Andaz for the price. I also think it’s on the best resort beach on Maui.

But I’m also a Marriott Bonvoy member which often pushes the Wailea Beach Resort to the top of my list.

Soooo much info on my specific Maui hotel recommendations here >> Where to Stay on Maui

And if you’re visiting Maui on a budget, or you prefer more space, I’ve got a pretty comprehensive breakdown of where to book condos on Maui here >> Maui Condos

On Kauai, the north shore is hands down the most beautiful part of the island, but I usually opt to stay in sunny Poipu on the south side and do day trips up to the north shore. Read the pros and cons of staying in Princeville vs Poipu plus my specific hotel recommendations here >> Where to Stay on Kauai

On the Big Island, I like to stay on the Kona side of the island because it’s where the best beaches and resorts are but the island is so huge that some people like to do a split stay and stay 3-4 days on the Hilo side and 3-4 days on the Kona side >> Kona vs Hilo

Also, the Big Island has some of the best beach resorts in Hawaii. I’ve ranked them all here >> Big Island Beach Resorts Ranked The Mauna Kea Beach Hotel has a prime location on what I think is the best beach in Hawaii. But the Four Seasons Hualalai, Kona Village, and Mauna Lani Resort all get top points for luxury.

On Oahu, you’ll find the best deals in Waikiki and it’s a great basecamp for exploring the island. The Royal Hawaiian is iconic, but you can find such good value for the money at smaller boutique hotels like the Laylow, Kaimana Beach Hotel, Surfjack, Wayfinder, etc. >> My Favorite Boutique Hotels in Waikiki

But if you want a real vacation and to see the best parts of the island, you’re going to want to stay outside of Waikiki >> Where to Stay on Oahu BESIDES Waikiki I personally love staying in Ko Olina at Disney’s Aulani Resort or the Four Seasons and can’t wait to stay at Turtle Bay on the North Shore now that it’s joined the Marriott Bonvoy family as a Ritz Carlton.

Tips for saving money on hotels?

YES….SO MANY! I love staying in a fabulous hotel, but I’m always looking for ways to save some $$$.

Some of my best tips:

Do a split stay. Spend the first part of your trip at a more budget friendly hotel or condo and do the bulk of your “exploring” and sightseeing. And then switch to a nicer place the last few days and just “vacation.” You’ll get the best of both worlds.

Visit during shoulder season. There’s not much of an off season in Hawaii anymore, but I usually find the best rates on hotels in late April through May and late August through September.

Also, just picking the “right” days can save you a bundle. Prices vary throughout the month and even week (especially if standard rooms are sold out for certain dates and they’re showing you the price of a suite). If you can view the 30 day calendar and pick your dates more strategically, you can save $$$.

More details here >> How to Save Money on Hotels

But my FAVORITE way to save money on hotels is TRAVEL HACKING. I’ve done THREE trips to Hawaii in the last 18 months staying at luxury resorts for FREE using credit card points.

Here’s how I do it >> Travel Hacking Guide