As the former owner of Maine Watercraft Rentals, where I used to rent boats to my vacation renters that stayed in my vacation rental homes - a lesson I learned the hard way to never do again, I will tell you DO NOT DO IT. Don't offer bikes, golf carts or watercraft at your rental - ever. I wouldn't wish it on my worst enemy.
Reason 1.). You cannot get insurance coverage for the actions of the renters, and neither can they. You can only insure your watercraft for your own use. If the renters hit another boater, kill someone swimming, or cause any damage anywhere, you will be the first entity listed in the lawsuit. Again - learned this the hard way. Yes, you can 'google' and find insurance for P2P rentals (more below), but when you get deep into those policy coverages, you'll see they won't cover you if the renter is intoxicated (a recent survey found that 72% of Americans drink alcohol went renting vacation homes), and won't cover you if there is a mechanical issue.
Reason 2.) You can never know the operating condition of your watercraft unless you are present. If the steering starts to go, and an accident happens, you are screwed! If you look at the exclusions for coverage for any boat rental policy, they state they will not cover any claim for the following reasons:
"This insurance does not cover: a. Any loss caused directly or indirectly by wear and tear, gradual deterioration, mechanical or electrical breakdown, overheating, ice or freezing, galvanic action, rot, mold or mildew, corrosion, electrolysis, weathering, marring, scratching, denting, vermin, animals, marine life, or insects; " The keys words in there that are "mechanical or electrical breakdown". Those are the two reasons a boat fails to operate properly and an incident happens. If the steering locks up or an electric short happens causing a fire - that's it. You are on your own.
Reason 3.) Peer to peer (P2P) insurance policies are difficult to understand and even harder to get payouts on. There are important differences between P2P boating insurance and recreational boat owner's insurance. During the rental, your renters could be subject to different insurance terms than what you may think they are for. For instance, the geographical area they are permitted to boat in is likely to be different.
Reason, 4) Do you have the time in your life to invest in a lawsuit when it happens? It's not a matter of 'if' and accident happens - but 'when'. When it does happen, even if you dotted your 'i's' and cross your 't's' and have an ironclad agreement and insurance in place (which isn't possible with a boat rental - you can't sign your life away), you'll be invested in a 3 year process, minimum, almost daily, of addressing a lawsuit to decide on the value to be paid to your renter for the accident. In this case, which was a win for the renter - the rental boat owners still had to pay hundreds of thousands out of pocket before the insurance covered it and invested over 2,400 hours of their life to work with lawyers and defend themselves. They will never get that back.
If you do offer paddle-craft at your rentals - be sure to review these two documents, one that has instructions for you between rentals and one that you should post for renters to see. Also, be sure to watch this video on paddle-craft safety at short-term rentals.