It sounds like some people are conflating purchasing "leasehold" properties vs simple outright purchase.

In Hawaii, many properties are sold as "leasehold" because the department of Hawaiian Homeland Trust (and sometimes other entities) are the owner of the land and manages much of it via "leasehold" titles. This is relatively rare in the contiguous states and most centers around Indian reservations in the contiguous states.

In Hawaii, it's managed as leasehold because many of the trusts forbid selling the property, and the trustee uses the lease fees as income for the trust while always owning the asset. In Hawaii it's sometimes confusing because the Hawaiian Homeland Trust is a quasi governmental organization supposedly managing the trust for the benefit of Native Hawaiians.

There is no "Native Hawaiian" provision to purchasing a leasehold, and many of the leaseholds have a near perpetual renewal provision making the effective ownership rights nearly identical. Leaseholds that do expire can sometimes cause issues when trying to obtain a mortgage for the property, especially if the leasehold is shorter than the proposed mortgage term.

 

My aunt and uncle bought a condo, and retired in Waikoloa Village, on the Big Island. They love it! It is easy for them to fly to HNL when they need to...

 

Waikoloa is pretty amazing! I love the Hilton there actually, like 9 pools, including sandy bottom ones for the kids. A natural lagoon with turtles always hanging out. Like 60 acres, you can ride the boat, tram or walk between buildings that have all kinds of Ming Dynasty art work that were put into the hotel when it was built.

Do the night Manta Ray dive right off the coast there (although you depart in Kona Harbor), and I've done it as a night dive and snorkel and prefer the snorkel as the manta come from the depths and scoop up the krill that are attracted by the light arrays the tour companies lie on the sea floor. The dive you end up looking up the whole time which I found uncomfortable. On the snorkel your in perfect position to see the action.

 

Went to a luau there once when the kids were young. Had a brother in law that lived there in the Village. Cool place.

 

Actually common enough for park land cabins. Cabins are allowed on some park lands but the land is still owned by the government, and the lease is for a finite period. Sometimes the land is reclaimed at the end of the term, more often renewed.

 

You are referring to the Hawaiian Home Lands program. It is very limited and restrictive.
Most single family houses by far are fee simple. Condos are a mix, most are fee, but not all. Even a particular building which is owned by an entity may have some fee and some leasehold units, or all leasehold. Terms vary and some offer the fee interest for sale, some don't.

 

We have one grandfathered in near Tahoe on federal land. We have to graze a certain number of cattle every year to maintain the grandfather clause. We don’t own nada. They would take this back in a nanosecond if they could. Thank god california used to be a red state.

 

In general, Leaseholds in Hawaii deal with condo's if you are looking for an investment or primary residence.

You can normally buy these for more than $100k less than traditional Fee Simple condo's in the same area.

Typically a poor resale investment unless you are in the retirement age and aren't worried about when the lease is up on the building and land. Leasehold's are often on the market much, much longer than Fee Simple properties. Sometimes years.

When I am browsing for investment property in Hawaii, if I see a beachfront condo going for something really low like $300-$350k, it's almost a guarantee it's a leasehold.