Maui Accommodations


Maui contains about 728 square miles of land. So now that you’ve decided that you’re definitely on your way to the island, the next step is to figure out what piece of that land you’ll be copping a squat on during your stay.

The island is broken down into six different localities: North, South, East, West, Central and Upcountry. Do to factors like trade winds, mountain ranges and varying levels of elevation you will find many different types of climates on this little lava rock that we call Paradise. Like everything, each section has its pro’s and con’s.

Here’s the run down…

Northside: Paia Town, the surfing, kite surfing and windsurfing hotspot of the universe is located on Maui’s North Shore. Paia sits right at sea level so it tends to get hot…but that’s what you’re looking for, right? The weather is generally dynamite…lots of sun, nice trade winds, and the beach is so close to the town’s main strip that when you’re walking the street you can sometimes hear the waves crashing and feel the light spray of the sea.

Shacking up in Paia is for the adventurous “I love the feeling of sand between my toes, and salt on my skin…all day long” kind of person. You also have to be pretty open minded to appreciate all that Paia has to offer… Paia is not for the faint of heart or those that are easily offended. Out of all of the spots on the island, Paia is truly a melting pot of different cultures. Modern day hippies with designer patchwork pants, old time hippies wearing tie die clothes that you would swear haven’t seen a washing machine since the early seventies, tattoo artists dripping with body jewelry, tan locals hitching a ride with a soda in one hand and a boogie-board in the other, golden Europeans sipping lattes, tourists from all over the world enjoying the hustle and the bustle…you name it, Paia’s got it.

So if you’re one that likes to explore and take in the true modern culture of another place, loves the beach, likes feeling sticky and salty twenty-four hours a day, has a serious caffeine addiction (i.e. coffee available around every turn…but no Starbucks), is attracted to hip and novel shopping experiences, and/or enjoys walking around town half-naked (or watching the people who do) Paia is the place for you.

What you will not find is a luxury resort or a soul that gives a hoot that your khaki’s are now covered in “red dirt” (from the near by cane fields) stains. But you will find several great bed and breakfasts that will take great care of you and ensure that you’ve got great beach access and don’t miss a second of the fun that this individualistic town has to offer. For North Side accommodation suggestions see our Recommendation List.

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Southside: Kihei, Wailea and Makena…Some of Maui’s preferred vacation nooks are located on the south side of the island. Kihei, Wailea and Makena are the spots of the island that you will usually see advertised as “Maui”. Beachside condos, tourist traps, luxury resorts and spas, “shave ice”, open air markets, umbrella drinks, suntans to kill for, sunburns to die from, bikinis, roller-bladers on side walks. Kihei is reminiscent of a clean Southern California boardwalk. Wailea is 100% luxury. Makena is old Hawaii meets a million dollars. If they were sisters, Kihei would be the Party Girl. Wailea the Aristocrat, and Makena the Earth Mama in Prada.

The weather is dry out in Kihei, perfect for slathering on tanning oil and sizzling away till your heart’s content at one of the awesome, family friendly beach parks. The beaches in Kihei are filled with locals and visitors year round. You will not find privacy on the sands of Kihei, but you will find great weather, generally low wind and nice swimming conditions, and lots and lots of people watching.

The main type of accommodation in Kihei is the condo rental. You can find anything from super-budget to high-class. Most are located just a hop skip and a jump from the beach and are close to fun activities and nightlife. For Kihei accommodation suggestions see our Recommendation List.

As you head out further south toward Wailea you’ll notice a climate change…the grounds get lush, there’s a lot more shade, and the breeze is definitely cooler. We locals can’t quite decide if it’s because of the mountains back-dropping Wailea or just great planning skills by developers. I guess it doesn’t really matter, because whatever it is, it works. Wailea is the type of place that makes you say, “Ah, luxurious”. It’s also the type of place that will bleed the money out of your wallet before you even know your cut. But if your budget allows it, please take our word for it…if you want to feed your island fantasy, Wailea is the place you’ve got to be.

Wailea is the home of the luxury resort, luxury dining, luxury shopping, luxury lounging, luxury golf, luxury beach…get the picture? What you won’t find in Wailea is a ton of locals (unless we’re working at the resorts)…the truth is that Wailea is just really expensive and most local people can’t afford to live or play there. But it is beautiful, and when we do get out there it’s usually to play tourist just like you. For Wailea accommodation suggestions see our Recommendation List.

Even further South from Wailea is Makena…a beautiful, almost “off the beaten path” kind of place. Oneloa Beach (Big Beach) is arguably one of the best beaches in the world. The beach is huge (3,000 feet long), with three entrances and paved parking areas. Parking can be hard to come by, but the frustration is worth it. The parking lots may seem packed, but I promise that you’ll be able to find your own little section of nautical heaven on the beach. Makena Beach is cozy, grand, romantic and basically a bunch of fun. Back in the late sixties and seventies hundreds of transients set up camp on the beach and called it home. When you dig your toes into the sand, you’ll know why…you’ll want to live there too. 

Makena has a “shore break” meaning that the waves break right on shore. This means that ocean fun should consist of frolicking around in the waves, body boarding, skim boarding and body surfing…it’s not a place to surf…don’t do it. I once saw some poor people attempting to long-board there and it wasn’t a pretty picture. Most of all, it was very dangerous. Remember, if you’re going to Makena bring fins, not a surfboard. Consider yourself warned. (There are a few sections of Makena that are okay for surfing, but only for people who know the waters extremely well)

As a note, head out to Makena beach first thing in the morning. On a typical day the clouds begin to roll in at around three in the afternoon.

Makena is basically the beach; an island get away at it’s finest. You can find a vacation rental in Makena, usually with a hefty price tag and a high minimum stay. The greatest thing about Makena is that you have the feeling of seclusion while being just minutes away to the “more happening” Kihei and Wailea. For Makena accommodation suggestions see our Recommendation List.

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Upcountry: Upcountry, Maui is my favorite place on the island. Nestled on the slopes of Haleakala, it is truly a section of the island that offers tranquility, inspiration and healing. Because of its elevation level, the climate Upcountry tends to be very different from the rest of the island—cool breeze and lots of eucalyptus, pine and jacaranda trees. The air is different here up on the mountain—cleaner, fresher, thinner. There are often refreshing daily showers that bathe the abundant pastureland until it shimmers. Upcountry is a place to escape to, a place to listen to your heart.

Makawao Town is the center of it all. In fact, local residents have dubbed it “The heart of the Planet”—the place where all good energy circulates. It can be a fantastic spot to vacation. It’s conveniently located just fifteen minutes from the airport, fifteen minutes from the beach, and only about thirty-five minutes from the resort areas of the Southside. The perk is that while you’re close to everything, you’ll still feel like you’re a million miles away.

Makawao Town has a handful of high-end boutiques, salons, natural health practitioners, a general store, bakery, and even a medicinal herb shoppe. Think: the Beverly Hillbillies find Buddhism… 

If you want magic, in the figurative and literal sense, body and soul conscience Makawao is the place to be. Common sights are cows (named “happy cows” by the local dairy), quaint, old buildings erected in the days of the Paniolo (Hawaiian cowboy), locals horseback riding down the road, kids of all backgrounds and ages cruising the sidewalks, old guys playing chess, a musician on the corner strumming on his guitar…

Makawao is special; eclectic like Paia but more refined. The people are friendly and will chat your ear off for hours if provoked.

You won’t find a real fancy place to stay here, but there are a lot of clean, comfortable, historic bed and breakfast’s that are run by some of the most dedicated and knowledgeable hosts on the island. 

If you’re a reader, writer, artist or hopeless romantic you’ve got to stay in Makawao. For Makawao accommodation suggestions see our Recommendation List.

As you head further up the hill toward the summit of Haleakala you’ll reach Kula. Kula is a very quiet, minimally developed (besides local residence) area of the island.

Kula is the crème of the crop. The Realtors are always saying, “location, location, location”. You’ve heard it, haven’t you? Well, Kula’s high elevation, and low rolling hills provide the best, and I mean the best views of the island. On a clear day you can see all of Central Maui, North Maui and South Maui, Molokini Crater along with the island of Lanai, Kaho'olawe and sometimes Molokai—beautiful in the day, stunning at night. It’s also a fantastic place for stargazing.

The problem being that if you’ve come to escape the cold, Kula may not be your first choice. Most of the time you’ll need a space heater or fireplace (yes, year round) to be comfortable at night. If you like getting bundled and cozy to sleep, rest assured that by mid morning the temperature will be comfortable and by mid afternoon it’ll be blazing hot.

There are no hotels, but there are a few lodges that overflow with 100% country elegance. Staying up in Kula is like time traveling to a simpler place in history long forgotten. For Kula accommodation suggestions see our Recommendation List.

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Eastside: Welcome to the jungle! East Maui weather tends to be muggy, damp and intensely tropical…in the best possible way. 

In East Maui you’ll run into some of the island’s most memorable sights: vibrant double rainbows, powerful waterfalls, and thick trails filled with rustling bamboo and trees heavy with succulent island fruit like guavas, rose apples, and papayas. Things grow wild and strong here.

Unfortunately, pests like mosquitoes and rodents are hip on the East Maui scene as well. So, if you squeal like a pig at the sight of a rat or break out into hives with every mosquitoes bite, you might want to reconsider adopting East Maui as your home away from home.

The weather is warm, the air is thick, and the ground is damp—kind of like one big greenhouse. East Maui is Maui in its most raw form. You’ll find flower farmers, fruit stands and barefoot kids engaged in rotten guava fights (serious business to an eight year old) around every bend.

The land becomes more and more secluded and pure the closer you get to Hana from the “more or less” domesticated East Maui town of Haiku. There are no hotels outside of the high-class Hotel Hana, but you’ll find a lot of bed and breakfasts and vacation rentals.

Travelers beware….East Maui has a tendency toward pulling the “Lord of Flies” spirit out of people. You just may find your savage self and never want to come back to modern day life.

The only downfall that East Maui has is that you are so far away from everything else. It’s a great place to spend a few days of your vacation but as far as staying anywhere East of Haiku, don’t plan on it for the entirety of your stay. You don’t want to spend a third of your hard earned vacation cooped up getting motion sick from winding roads in your rental car… For East Maui accommodation suggestions see our Recommendation List.

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Central: Central Maui—Kahului, Wailuku and Ma’alaea, is located on the isthmus between East and West Maui. Kahului and Ma’alaea are located at sea level. This means hot, dry weather that is similar to Kihei. Wailuku has a slightly higher elevation (331 feet) and is a lot cooler and cloudier than the rest of Central Maui.

The good thing about lodging down centrally is that you’re pretty close to just about everything. The bad thing about it is that you’re going to be submersing yourself into an area of the island that doesn’t take much time to cater to tourists. With the exception of Ma’alaea, Central Maui is not a vacation section of the island, it’s more of a real-life, going to work kind of place…and that’s what you’re trying to escape, right?

Ma’alaea would be your best choice…the closest thing to a resort town that you’ll find down here. Down by Ma’alaea Bay, there are nice views of the ocean, Haleakala and the West Maui Mountains. Over the past decade, Ma’alaea has gone from sleepy little community with a few condos, and a couple of restaurants to quite a happening little spot…shopping, activities and the famous Maui Ocean Center.

For Ma’alaea accommodation suggestions see our Recommendation List.

Second choice when it comes to staying in Central Maui would be Wailuku. Wailuku is a town that is rich with history. It’s a town that even with all of its recent development has remained quite the same…old plantation houses, old theatre buildings, the Bailey House museum (preserved missionary house) old, old, old… Wailuku is filled with local people and it is where the County Building, Maui Community Correctional Center, and State Building are located. 

The pros for staying in Wailuku are for its quirky, local-style, and no BS type of atmosphere. The cons are the same as the above. Also, there are certain nooks and crannies of Wailuku that you just really don’t want to find yourself lost in. Some locals, especially those that feel slighted by “foreigners” would not take it lightly if they feel that their personal space is being trampled on. As a side note, what they deem their “personal space” can vary daily, so tread softly.

Wailuku has some comfortable and clean places to stay—no resorts or hotels. Do your research and ask a lot of questions. Remember that while most places in Wailuku are relatively affordable, if the price sounds too good to be true it probably is. You get what you pay for. For Wailuku accommodation suggestions see our Recommendation List.

Kahului is not the Hawaii that you see advertised, and it is not the Maui that you dream of at night. It’s functional and practical. There is nothing luxurious about it. Now, don’t get me wrong…there are lots of things to do in Kahului—movies, shopping, eating…but there’s no added flare. There is a strip of little hotels that offer an okay night’s stay, but with all of the other great places to be on the island, why stay in a motel on the side of one of Maui’s most congested roads? Also, these motels may advertise that they are “beach front” but in reality they are “harbor” front. The harbor is not the cleanest place in the world and these motels are local icons for a random night’s stay of partying and (dare I mention it?) “affairs”. Trust me on this one…harsh as it may sound, it’s the truth. Ask any local if they’ve ever stayed at one of these places and if you get a nod, you’ll also get a telltale grin. If you’re dead set on it, check our Recommendation List for Kahului hotels.

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Westside: The west side of the island—Lahaina, Ka’anapali, Honokowai, Kahana, Napili, and Kapalua, is a popular and fantastic place to stay on Maui. When the weather on the rest of the island is less than optimal, the west side usually holds up its end of the “I came to Maui for some sunshine” bargain.

The beaches are clean, the shopping is fun, the people are friendly, the lodgings are high-class and the history is rich. What more can you ask for? How about access to just about every activity there is—from horse back riding to sunset and cocktail sails? How about good music and fun bars? How about world-renowned shows? A round of some of the snazziest golf on the planet, anyone? You name it…the Westside has got it.

Lahaina is an old whaling town and used to be the capitol of Hawaii back in the day (until 1840 when King Kamehameha moved the capitol to Honolulu). The beaches are popular with the local’s…consistent waves and good swimming. Lahaina is hot, dry and dusty. It’s a great place to eat shaved ice and wander around on a lazy day.

There is so much to do in Lahaina, and you can find most of these things on Front Street. Front Street goes on for a few blocks and is filled with shops and restaurants that cater to tourists…mostly tourists with money. It’s a fun place to shop and mingle, with beautiful people (and even parrots) lining the sides of the road.

There are a lot of nice places to stay at in Lahaina, from the moderately priced condo to an old time luxury inn; you’ll have no problem finding somewhere that meets your needs.

As you drive further west from Lahaina the next spot that you’ll hit is Ka’anapali. Ka’anapali is translated “rolling cliffs” and while it is hot and dry like Lahaina, there is more foliage and therefore tends to be a little bit (teensy bit) cooler.

Ka’anapali has some of the most pristine swimming and snorkeling spots on the island. Shopping is fun, and the restaurants are reputable. Prices out in Ka’anapali tend to be comparable to Lahaina, meaning a little more than most of the island, a little less than Kapalua.

There are no shortages of hotels and condos to choose from in Ka’anapali…most are pricey, but all are worth the stay. For Lahaina and Ka’anapali accommodation suggestions see our Recommendation List. 

Honokowai and Napili have been called the “Kihei” of West Maui. This is due to the towns’ high condo content. Both tend to be more affordable than the other places in West Maui (but still not budget). There’s not too much in the ways of shopping, but this can be a good thing if you want some peace and quiet while still being a hop real close to the hustle and bustle of Lahaina.

Honokowai has a beach with tide pools that is ideal for little kids, and Napili has a few really beautiful beaches that are ideal for swimming and snorkeling.

There are tons and tons of condos in this area and a few nice hotels that are generally low-key and laid back while still providing quality accommodations for travelers. For Honokowai and Napili accommodation suggestions see our Recommendation List.

Kapalua is first class, high class, and popular with the celebrities and golfers. Kapalua is home to some of the most prestigious golf courses and resorts on the island. Kapalua tends to be cooler and definitely lusher than the other areas of the Westside. Locals think that it has a climate that is closer to Upcountry than West Maui.

Kapalua looks like money and have no doubt that it’s going to take a lot of the green-stuff to stay out here. It’s worth it. Kapalua is like south Maui’s Wailea. It took a heck of a lot of money to plan and build, even more to maintain it, and has a fancy reputation to uphold, so expect to financially contribute to its beautification.

Restaurants? Only the best. Cuisine from around the world. There is no doubt that even the pickiest food critic in the world would never utter a negative word about the menus offered in this resort town.

Beaches? Oh yeah, don’t worry about the beaches. They are well behaved, not over crowded and clean. There’s nothing more to say besides the fact that Kapalua is Maui at its finest.

To feel like a million bucks and/or to blow a million bucks stay in Kapalua. It’s like being royalty, and we all deserve that once in a while. For Kapalua accommodation suggestions see our Recommendation List.

I see only two problems with staying out on the Westside. The first problem is that there is no hospital out there. I know it’s not something that you want to think about on your vacation, but believe me; it’s going to be a huge deal to you if you find yourself or a loved one in a medical emergency during your stay. The second problem is that if there is a car accident on the Pali (the main way to the West Side) and the road is shut down you can be stuck in traffic with no way out for hours. Literally, hours…like a very long and frustrating time. It’s gotten so bad in the past that people turned off their engines and started tailgating with fellow would-be-drivers…no joke. Now put the hospital and the traffic problem together and you have a super bad situation. Although unlikely, it is something to be aware of.

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Your next big decision is what type of accommodation will work best for you. Maui offers five basic types: resorts, hotels, bed and breakfasts, condos and vacation rentals. 

If you’ve already decided what area of the island you’ll be staying in, you’ve already narrowed down your search. Some parts of the island are equipped with only a handful of accommodation options. On the other hand, if you are like most people and are choosing to land yourself on the south or west side of the island you have many different options to choose from.

Here’s what the different types of accommodations have to offer:

Resorts: What’s not to say about a resort? You have full room service, spa access, ambiance, security, gorgeously designed grounds, fine dining and shopping, location and luxury all at your fingertips. This is it…this is heaven. The downside? It’s going to cost a lot of money. Not that you expected all this to come free…yeah, it is heaven, but on earth.

Hotels: Hotels offer some of the amenities of a resort. Most have limited room service, moderate security, a swimming pool etc. Hotels tend to be close to the activities and well enough kept to be comfortable. While they might not offer the glamour and glitz of a resort, they do try to maintain a cetain level of luxury.

Bed and Breakfast: This is the forgotten jewel in the accommodation chain. Bed and Breakfasts are for people who want to feel at home while vacationing. Most are located in older, historically restored plantation homes. Hosts of B&B’s are overly accommodating to guests (hey, you’re their bread and butter) and usually have a genuine interest and knowledge of the island. If you want to experience the “real” Maui Bed and Breakfasts are the way to go.

Most are clean, comfortable and have kitchen access. The drawbacks are that the majorities do not have pools (there are a few that do) and security can be an issue. If you want a lot of bedroom privacy, don’t count on the B&B to provide it, as you’ll probably have “neighbors” across the hall.

Condos: Condos are scattered throughout the south and west sides of the island. There are a lot of options for you out there if you are a condo person. They offer a lot of space at a reasonable rate—great for families. They have pools, nice grounds, and are usually located on the beach or right across the street. No room service, but most condos have laundry facilities along with good stuff like microwaves and dishwashers in all of the units. It’s a good option for people or families that are planning on spending a considerable amount of time on the island.

Vacation Rentals: Vacation rentals are houses or cottages that owners rent out for all or part of the year to visitors. They are usually well kept and are scattered in beautiful nooks and crannies all over the island. 

Price range varies and so do the amenities. You can get anything from a huge stucco beach house in Makena to a little cottage surrounded by pineapple fields. Do your research. If you’re interested, some people are into trading houses for the summer or winter—an interesting option if you own a rental in a good location.

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