Been looking at Vrbo and similar sites. Found a place with good reviews, no weirdly written reviews that raise red flags, no weird gaps in review timeline, not all glowing five-star reviews, etc.

Sent the booking request and got an acceptance from the owner who then calls me and thanks me for booking and offers me a discount option.

Says if I would like, he can cancel the booking through Vrbo and then we can do the booking directly with a contract via email and I can pay cash when we arrive.

Sounds fishy, obviously. I asked. So he told me that the reason is two-fold:

1) Honulu County currently has limitations on rentals. Can rent to only one group on a 30-day period. This allows him to possibly get around that because it's not tracked. Many listings mentioned this 30-day issue and then had statements about calling the owner to verify or other things, that sound like maybe this is common for owners to do to skirt the rule.
2) Off Vrbo eliminates the Vrbo markups. Also guessing he doesn't report the sales tax, at least; and maybe also trying to hide income tax, as well.

Anyway, I don't care about either of those things as the renter. Not really my obligation if he's not following the rules.

It does obviously still make one a bit leery. He acknowledged it's a bit fishy sounding. Said I could check the parcel ID required to be listed on Vrbo and confirm it's his property per county property tax records, etc.

Anyone ran into this before... Or even done this yourself with your own rental?

Maybe travel insurance would cover something like this and I could get that and still pay less overall?

What say ye, CB?