First Time Investor - Looking to buy Waikiki Vacation Rental

3 Replies

I’m buying my first home, a condo in Waikiki. When I depart Hawaii in about 3 years, I plan to keep the place as an investment property. I have a choice between a cheaper place ($330,000) that would only be suitable for long term rentals, or a more expensive place ($440,000) I could use for 30 day or more vacation rentals or long term.

Can’t do anything less than 30 days though due to HOAs. So I’m looking for info on the 30 day+ rental market in Hawaii. I want to figure out if the potential cash from using the more expensive property for vacation rentals would offset the higher cost eventually or at all. Help? Thanks!

I think it could be worth it to do the 30 day rental, but it will depend on your manager. That could make or break the returns. Also, airdna is a good resource for STR rates.

Just a small heads up on your purchase assuming the 30 day+ Vacation rental. The way the current law is written, advertising on AirBnB even though you put parameters of minimum 30 day stay is still illegal since the way its marketed is as a "Nightly Rental". Also, with the new laws, there may be a lot more competition from other Landlords for the 30 day+ Vacation Rental market. It just looks like the trend right now is to make renting out your property as a vacation rental harder and harder. Something to consider when making your choice.