The house is rented as a STR on AirBNB for $600+/night and is totally separate of the horse farm part.

Investment Info:

Townhouse buy & hold investment in Carolina Beach.

Purchase price: $365,000

Cash invested: $22,000

Contributors:
Danielle Gillespie

Short Term Rental 1 Block from...

. - Channel Manager: Guesty - allows you to list your STR on multiple platforms (Airbnb, VRBO, etc.) and manage it all from one place.

What I want to know, is it really worth it to own a STR on the Big Island? 

--It's not a good idea to report an STR on Sch C instead of Sch E if there are no substantial services, even if there is a loss, as that would generally improperly reduce income subject to SE tax and mess with your calculated eligible contribution to an SE retirement plan. 

I am looking into buying a STR on Sanibel Island.

I just did this for an investor in NY for a 2.5 million dollar STR on Indian Rocks Beach and it grosses 400k per year.

I have 2 LTR in Maryville and considered trying STR on one but in the end I didn't want to spend the money to update and furnish it as I wasn't confident it would pay off. 

For instance, I just looked at Orlando FL and if I'm reading it right, it appears that they don't allow STR on residential (R) zoned districts.

I have lots of ideas for luxury STR on lakes is Minnesota and Wisconsin to make them stand out, but struggle with the funds and finding people that want to partner with a first time investor.