Try Living In Hawaii For A Week

Posted May 10, 2011 at 2:16pm
Sunbathing woman sleeps on a beach.

For most people, living in Hawaii won't be as leisurely as vacationing in Hawaii. Except maybe on the weekends! (Photo credit: patrick kiteley)

So you’ve already thought carefully about the impact a move to Hawaii would have on your family, and you’re OK with any sacrifices you’ll have to make. And you’ve done some research on the different Hawaiian Islands and narrowed it down to one or two that you think would best suit you and your family. You can’t wait to pack everything up and move to paradise.

But before you spend lots of time, money, and effort uprooting your life and moving it all overseas, it’s important to make sure that you really do want to live in Hawaii. At this point, that may sound like a no-brainer. But sometimes people think they want to live in Hawaii, but what they really want is to be on permanent vacation in Hawaii. What they love about coming to Hawaii is not necessarily unique to Hawaii itself, but being able to get away from the daily grind of waking up early, commuting to work, making dinner, cleaning the house, taking out the trash, helping the kids with their homework, etc.

Unless you’re fabulously wealthy and can afford to move into a suite at the Trump International Hotel, where your every need will be taken care of by their attentive staff (a girl can dream, can’t she?), your daily life in Hawaii probably won’t include maid service, room service, breakfast buffets, or a work-free schedule.

To make sure you really do want to be a Hawaii resident (and not just a permanent tourist), you should plan a trip to the Hawaiian island that you think you’d like to eventually move to — at least a one-week stay. If you can afford it, stay longer. If you’re not totally sure which island you want to move to, you’ll probably want to stay longer so you can do some island hopping.

Everyone who is part of your planned move to Hawaii needs to come along on this trip. But don’t think of it as a vacation. Your goal for the week you spend in Hawaii will be to live your life as close to the way you do now in your current home.


Choose accommodations that match your current lifestyle and financial means. If you currently live in a detached house, ask yourself if you would be able to afford such a house in Hawaii. Check current real estate listings to make sure. If you discover that you’re more likely to be living in a condo, townhouse, or apartment, then that is the kind of accommodations you’ll want to seek out. Short-term condo rentals are not hard to find, and some are even cheaper than hotel rooms.

Interior of a house, showing the kitchen and part of the living room.

If you can afford it, book a short-term rental home for your stay. It will feel more like you're actually living in Hawaii than if you stayed at a hotel. (Photo credit: Michael Ocampo)

If you’re still able to afford a detached house in Hawaii, then try to find a rental house to stay in. This can be a challenge, though, as listings for short-term/vacation rental houses tend to be high-end, luxurious beachfront estates with sky-high nightly and weekly rates. Most budgets will require something less expensive, and unfortunately detached houses in a lower price range are hard to find as short-term rentals in Hawaii. You might need to settle for a condo or hotel room instead.

Here are some good places to find all kinds of short-term rentals in Hawaii:

  • Airbnb: Whether you’re looking to spend $29 a night to sleep in someone’s living room or $4,000 a night to stay at the Kailua estate where the Obama family spends their winter holidays, there is something for every budget on this awesome site. (Why I’m not recommending Airbnb anymore.)
  • Craigslist Hawaii: Check out the listings under “Housing”: “Sublets/Temporary” and “Vacation Rentals.” You might want to also look under the general “Apts/Housing” category, because sometimes people post listings for short-term rentals there, too.
  • Honolulu Board of Realtors: This site includes rentals for all islands, although at the time I checked it, most of the listings were for Oahu. Still, it’s worth a try if you’re looking to stay on another island, as there are some relatively reasonable prices on here. Just be aware that this site also lists long-term rentals, so be sure to select “Short Term” or “Vacation” (under “Rental Type”) when conducting your search. Prices listed in the search results could be monthly or nightly rates, so read the details of the listing to find out which it is.
  • Aloha Living: This real estate site has a very handy search tool for finding vacation rentals by island, region, type of housing, size, and price range. (Note: Even their “budget” rentals can be pretty pricey, so you might want to start searching at that price range.)
  • Vacation Rentals By Owner: VRBO’s listings can be daunting — many of the listings are for outlandishly expensive oceanfront luxury homes and estates. However, if you dig deep, you’ll find some smaller, cheaper rentals, too, especially condos in Waikiki and the rest of Honolulu.
  • Polynesian Plaza: If you’re planning to stay on Oahu for a longer period of time, this place has one of the cheapest monthly rates I’ve seen online: $1,175/month for April-October 2011.

If you can’t find any short-term rentals that fit your budget, there’s nothing wrong with staying at a hotel. Just make sure the hotel you choose isn’t much more luxurious than the kind of home you’d be able to afford in Hawaii, and try to avoid using services like in-room dining, which you wouldn’t have in your home. Before I moved, when I tried living in Hawaii for a week, I ended up staying at the modest but clean Park Shore Waikiki, located on the quieter eastern end of Waikiki, right across from Kapiolani Park. The room was comfortable but basic, containing no luxuries that I didn’t have in my own home. And the free Wi-Fi Internet access in the lobby was very handy to have.


In a parking lot, a man sits on a red moped while his medium-sized dog sits on the moped's footboard.

During your stay, you might consider renting a moped rather than a car. In densely populated areas such as Honolulu, it's a cheaper way for residents (and sometimes their dogs, too!) to get around town.

Most likely you’ll want to rent a car — just make sure it’s the kind of car you’d be able to afford in “real life.” But if you envision using another form of transportation if you move to Hawaii, then you’ll want to try using that instead. If you like the idea of getting around by moped — a very popular form of transportation in Honolulu, where parking can be scarce and costly in some areas — then you should rent one of those instead of a car. When I was planning to move to Hawaii, I decided I wanted to try living without any vehicle at all. So during my one-week stay, I walked and took the public bus everywhere, just as I would when I eventually moved.

Daily Explorations

Since you won’t be able to go to work and your kids won’t be able to go to school, use that time during the day to explore different residential areas of the island. If your accommodations are in a tourist area, it is especially important to get out of there during the day so you can experience where the residents live. Depending on the length of your stay and your family’s needs and interests, you may want to use your daily exploration time to:

Leisure Time

Child with wide grin is buried up to his neck in sand.

Remember to enjoy some pau hana time: When work is done, have some fun! (Photo credit: Carissa Rogers)

Just as you would in your “real life,” make sure you take time to relax and have some fun. Although this trip isn’t meant to be a vacation, you do need to have some downtime each day. Hawaii residents even have a specific term for this: pau hana (“done work”), and it represents a philosophy that’s very much a part of the local culture: that life is meant to be enjoyed after the day’s work is done, especially in a place as beautiful as Hawaii. Otherwise, why bother living in Hawaii at all?

Reflection Time

Each day, discuss as a family your thoughts and opinions about that day’s exploration. Did anything make a positive/negative impression on you? Do you have any worries or concerns? Did anything surprise you? What adaptations do you foresee needing to make if you follow through with your plan to move to Hawaii? Consider taking notes during or after your daily explorations, while these thoughts and opinions are fresh in your mind.