Short-term Rentals in Maui or Oahu

9 Replies

Hi everyone,

I'm a new investor from San Francisco, CA and just started listening to the BiggerPockets podcast this year. I'm hoping to find an investment-friendly realtor in Maui or Oahu to help me find a condo that allows Airbnb and will cash flow. Anyone have any suggestions on how to get started? Any guidance would be greatly appreciated!

Thanks,

Tiffany

Based on my initial analysis STR Investing in Hawaii is very expensive and has lot of restrictions, HOAs. Unless cash buyers didnt make sense of ROI for leveraged purchase

Aloha @Tiffany Kho !  I'm an investor in STRs here in Maui.  I can help you look at and analyze properties. You can certainly cash flow if you are willing to do the work.  We've done quite well.  My wife is a pretty awesome realtor @Caroline Neubauer for investors because she was an investor in STRs and long term rentals here in Maui before she was ever a realtor.  Got the RE license to help us source more deals! I'm happy to talk you through the pros and cons of owning STRs here in Maui.  There are definitely things to watch out for. Feel free to DM me, and we can set up a time to talk.  

Aloha!

@Tiffany Kho hey Tiffany, I have worked with two excellent realtors here on Oahu, I write about each and the properties purchased in some of my posts if you want to check them out.

As others have mentioned the market here can be difficult but I will send you a message with their information!

-Rob

Hi @Tiffany Kho , we bought our first Maui STR in the summer, did a small rehab/reno and are now on the AirBNB/VRBO market. The bookings are starting to roll in, but we aren't cash flowing yet.

We used AirDNA to get a sense of the revenue potential. We still need some time renting to see how realistic that analysis is. 

Prices have jumped a bit since we started looking at the end of 2020 and prices in our complex specifically for similar units are up nearly 20% since we went under contract in April. I'd like to hear others experiences about that or how you're evaluating financials.  Our goal is break even since we see the place as our eventual retirement place, but ultimately the financial analysis if correct should be much better, especially in the long term with a 30 year fixed rate.

Good luck and keep us informed on how you do!

Bryan

Originally posted by @Mike Neubauer :

Aloha @Tiffany Kho !  I'm an investor in STRs here in Maui.  I can help you look at and analyze properties. You can certainly cash flow if you are willing to do the work.  We've done quite well.  My wife is a pretty awesome realtor @Caroline Neubauer for investors because she was an investor in STRs and long term rentals here in Maui before she was ever a realtor.  Got the RE license to help us source more deals! I'm happy to talk you through the pros and cons of owning STRs here in Maui.  There are definitely things to watch out for. Feel free to DM me, and we can set up a time to talk.  

Aloha!

Aloha Tiffany, welcome to reach out and happy to share what we're doing! Aloha! 

Tiffany - looks like you have some great connections on the Maui side of the house listed above. If you're interested in looking further into Oahu's STR market, let me know and I'm happy to help! Aloha

Wow! Thank you everyone for your responses! This is my first time using this forum and so far I'm amazed at how helpful the people on here are. I figured the best way to learn how to invest is to find people who have already done it and to gain knowledge from their personal experiences. I'm hoping to connect more with fellow STR investors.

I chose Hawaii because I've partnered up with my dad and he is looking for a place he would love going to for vacations as well. I'm  open to investing in other states though. I have a little Airbnb experience with Scottsdale but that house didn't belong to me.

We looked at a few condos in Waikiki's resort zone last week while on vacation but they were very expensive and didn't seem like the cash flow potential was there. It seems like Maui might be a better option.

 Aloha, Tiffany! Yeah it is pretty hard to cashflow at current prices unless you manage yourself. I own two STRs, in escrow on a third, happy to chat with you. I also know a great agent on Oahu if you're interested in that market.