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Many travel to the Hawaiian Islands and fall in love with the land and lifestyle. Perfect weather all year long, gorgeous scenery at every turn, family-friendly communities, there is a lot to love.

However, like purchasing real estate anywhere, there are some basic considerations as well as unique quirks to the real estate market in Hawaii. Buying real estate is a large financial decision and it is important that you have all the information you need to make a decision that is right for you.


The final concern is understanding each of the islands and their various residential areas. Each Hawaiian island has a unique vibe and personality. Within each island, there more urban and more rural communities. Moreover, each island is home micro-climates, where some areas are quite wet and other quite dry.

We live here on Maui, The Valley Isle, so it is our specialty. and we can direct you to the area that is going to meet your needs.


Hawaii has two types of property ownership in Hawaii: Fee Simple and Leasehold. Put simply, Leasehold is a scenario where the land is leased long term, and at the end of the lease it is renewed, or the property and its improvements all revert to the original owners. You will see this with condo units on certain islands. Often it will explain an unusually low-priced unit.

Fee Simple is the type of ownership that gives you total control over a property. Though of course you will be subject to any HOA rules and zoning.


Many purchase second or third homes in the Islands with the hope to be able to rent them out to cover costs while they are not there. This plan is doable, but it is imperative to understand the reality on the ground on each island.  

Most islands have highly restrictive laws on short-term rentals. Some, like the Big Island, generally require homes to be in “Hotel Zones.” Other islands will issue a limited number of permits for vacation rentals. The process to attain a permit is anything but simple and can cost thousands of dollars.

This is all to say that if you want to purchase a home that you can then position as a short-term rental when you are not there, you need to work with an experienced agent. We operate a vacation rental management and representation arm, so we are well-positioned to provide guidance on this front.


A great way to begin your Hawaii purchase process is list your “must-have” and “like-to-have” features.

How many bedrooms minimum?
What is the minimum lot size?
Do you require a home with AC – not all Hawaii homes have central AC?
Proximity to services?
Are outdoor amenities a must, e.g. pool etc?
Fixer-uppers okay or only renovated or new?
Do you want to be able to rent and monetize your property?


Besides doing a financial deep dive before you start your process, you are going to want to be pre-approved for a mortgage so that you are clear about size of the loan you will be able to secure. This will save you time and energy, as it will help to focus your search.

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