Hawaii Living: Where To Live

Hawaii Living: Where To Live
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Lucky you live Hawaii, but where exactly should you live in Hawaii?

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Luck We Live Hawaii. It's such a common expression here and the social media crowd loves it in its #LuckyWeLiveHawaii hash tag form. But where exactly would you live if you're moving to Hawaii? Let's cover the options.

Best Hawaiian Island To Live On

Well, that's a misleading title for sure! Why? Because there is no best island to live on. It really depends on what's best for you, given your unique circumstances. So let's go down the list of islands and see which is a best fit for you.


It's by far the most popular island for residents of Hawaii. With over 950,000 residents as of the 2010 Census, it's pretty obvious why Oahu is known as The Gathering Place. Oahu offers residents a lot in terms of infrstructure and options. Oahu offers a huge list of neighborhoods, schools, medical care, restaurants, stores, and so on. In terms if being the closest to a mainland big city, Oahu hits that mark better than any other island.

Those things also mean that employment options are better here than on any other island. You'll find more jobs in every sector (commerce, hospitality, industry, etc) than any other of the Hawaiian Islands. If you have to work for a living and want access to everything the mainland offers then Oahu is the smart choice.

This why Oahu is the obvious choice for more people who live in Hawaii. Of course, these pro's have their down side! For example, Oahu is the most congested island of the chain with some of the worst traffic you've ever seen.


Next up on the popularity dream list is Maui. For many, this is their dream island. Maui is good when it comes to infrastructure and many amenities. It has plenty of places to live, schools, shops, and so on. Of course, it only has a fraction of the places that Oahu has, largely because less than 150,000 people live here.

If you live on Maui you just learn to accept that a trip to Costco may mean a 30-60 minute drive because the island only has one. This applies to many things on Maui and for some, you just learn to live with it and plan for your needs better.

Even something as simple getting your car serviced at a dealer may be an issue on an island where there is no dealer for your car. In most cases, these aren't deal breakers and there are solutions, but it's worth keeping in mind that certain things are more complex here.

As with all islands, Maui jobs are often related to the tourism industry, but more so here than on Oahu. There are jobs in all sorts of categories here, but just fewer overall.

Maui gives a good mix of mainland convenience living and island life. This is why many retired people, who can afford it, choose to retire on Maui.


Kauai is another dream destination for many and countless visitors spend their vacation trying to figure out how they can live here. Kauai is much like Maui, but has even fewer amenities. You'll find fewer schools, fewer roads, and fewer job opportunities here. That's normal for a smaller island with around 70,000 residents.

Kauai can be a great place for those who want a much slower pace of life. It's great for those who don't need or care about material things as much. If you are good at living with less and happy making your own meals more often than going out, then Kauai might be your type of place.

Don't get me wrong, Kauai certainly has plenty of things to keep you going. This isn't a third world country! It's just that things are slower and people here like it that way. You might too!

Big Island

Hawaii Island, or the Big Island as most know it, has around 187,000 residents. It's actually the second most populated island after Oahu. Of course, it's bigger than all of the other main island combined so it feels less populated here.

In terms of amenities, infrastructure, and jobs, I would compare the Big Island to Maui. The difference here is that it's all spread out a lot more. Sure, the big numbers are around Hilo (east side) and Kailua-Kona (west side) but things are much further apart here. Jobs in tourism are common, as are plenty of retail type jobs, but you may not find a huge, diverse set of job opportunities available.

The Kailua-Kona side will be more touristy while the Hilo side is more local. While the island offers plenty of tropical feeling areas, much of it is black lava rock and feels like you're on the moon. Not everyone is a fan of that.

If you're the type that requires a lot of land to drive around then the Big Island is a good option. Getting from one side to the other takes around 2 hours. Traffic here isn't likely to be as bad as places like Oahu, Maui, and Kauai either.

If you're looking to live the recluse life in paradise then the Big Island might be a good choice. With so much land, much of it undeveloped, you'll find your paradise here.


I think of Lanai as a cross between Kauai and Molokai. It has areas that are completely off the grid and out in the middle of nowhere. Yet it also has some major resorts and an actual town area with restaurants and shops. The population here is small at only 3,100 or so.

If you need to work, Lanai may be tough place to live. You won't find many jobs here and when they do pop up there are many who want them. There's only a few dozen touristy type places (restaurants and hotels) and beyond that it's going to be slim pickings. Education options for your kids might be limited here as well.

If you love that really slow pace of life with a side of hippy and artist inspired vibe then this might be your island. This may well be Hawaii's tree hugger paradise. For many, things are a bit too slow here and there just isn't much to do. If you want anything that resembles a nightlife, you won't find it here. If you're young and dating it may be hard to find your match, but then again maybe they'd gravitate here like you did.


When it comes to living in Hawaii, few outsiders choose Molokai, even though it does have around 7,500 residents. That's probably a good thing. This is very much an island for those who were born here. You won't see as many outsiders on Molokai, compared to other islands, and if you did move here it may take a while before you're accepted with the locals.

Living on Molokai means accepting the fact that you're not going to be dining out much, education options are likely to be limited, and shopping options are few and far between.

When you need to do some shopping or have to get medical care then you're likely going to head over to Maui to take care of those things. That's a major deal for some, and the true definition of living in paradise for others.

Need a job? Good luck. Unemployment rates are high on Molokai because jobs are few and far between.

Which Side?

Once you've picked an island the next big choice is which side to live on. If you enjoy lush, green environments, and the wetter weather that comes with them, then the windward side is a good bet. This will be the bits along the north and east part of each island.

If you prefer dryer and sunnier weather then the leeward side might be better. These will be the sections along the south and west coasts.

If you can't stand the heat on either side then you'll want to look for elevation, often found inland on each island. The higher up you go, the cooler it will be. Then there is the wind factor. If you read Hawaii Living: Weather, then you know that we tend to live and die by the trade winds in Hawaii. These winds play a big part in keeping the islands from getting too hot.

Sometimes, too much of a good thing isn't so good. These winds come from the northeast and blow towards the southwest. You might find that a place on the northeast side of the island is far too windy for your tastes. Or maybe a place like Kihei on Maui is just too hot since the trade winds might not blow as strong here.

Spending time in several areas is a great way to see what you like. Of course, a lot depends on where you'll be working. The last thing you'll want to do is end up on the opposite side of the island from your job! Many think that isn't such a big deal until they're spending an two hours a day commuting.

Buying Versus Renting In Hawaii

If you're just moving to Hawaii you're probably excited about finding your dream home here. You're also probably in for some sticker shock. Even if you've researched properties you might be surprised as just how little you get for your money.

The median home price in Hawaii is around $550,000 USD. There are parts of the mainland where you could get many acres and a mansion for that kind of money. In Hawaii it may only get you a small condo or a 1500 sq ft house on a 3500 sq ft lot with neighbors so close you'll know what they eat every night for dinner.

Because of that, many are forced to rent. Personally, I don't like the idea of throwing money away on rent but I think it's a wise choice for somebody who just moved here. Spend 6-12 months getting to know the island before you decide where you want to settle down and buy a place.

Renting also saves you from the added cost of Home Owners and Condo Owners Association (HOA / COA) fees which can easily run into the several-hundred-dollars-per-month range. Read more about that in Hawaii Living: The Paradise Tax.

Leasehold Versus Fee Simple In Hawaii

When you're ready to buy you'll quickly stumble onto two important terms: Leasehold and Fee Simple. What the heck are these?

Leasehold Properties
A leasehold property is one where you acquire the right to occupy and use the leased property. That property might have a house on it that you own but the land under that house isn't yours. You're just leasing that land for a long period of time.

Just how long the lease is depends on many factors. For example, a condo developer may have leased the land from the land owner for 60 years starting in 1970. That means that the lease on the land is only good until 2030. A condo unit in that building may have re-sold many times, each time under the original leasehold agreement that expires in 2030. If you buy it in 2015 you would only have legal right to it until 2030. At that time it's possible the land owner would re-lease the land or decide to sell it. If the latter happened, you could watch your investment go away for good and be out of a condo.

Leasehold properties were very common years ago, but are less common today. When you do find them they will be far cheaper than a fee simple property. Personally, I couldn't imagine ever buying a leasehold property as my home but sometimes the deal is too good to pass on I guess.

Fee Simple Property
Fee Simple is basically what you're used to when buying a house or condo anywhere on the mainland (and most other places). You're buying the rights to the property and the land below it (at least so many feet deep, anyhow).

When you're looking for a place to buy, most people will only want to search for Fee Simple properties. Fortunately, most properties are Fee Simple these days as Leasehold is being phased out. Of course, even with Fee Simple there still may be other fees to deal with like HOA /COA fees and property taxes!


Obviously, choosing where to live in Hawaii is a big, complex decision. There are a variety of factors involved with the most common simply being tied to cost and job opportunities. Hopefully this article gives you a rough idea of what you can expect as you make your move to Hawaii. If you have questions feel free to ask them in our Hawaii Living Forums, we'll be happy to answer whatever we can!