Jim Doan is semi-retired at the relatively tender age of 58. He’ll tell you his secret: You can make money renting your possessions. He’s been doing that for decades, generating so much passive income that he no longer needs to work.

Doan started buying condominiums in Hawaii and renting them through VRBO two decades ago. Now he has an extensive stable of properties – with mortgages that have mostly been paid down by tenants – and he works just a few hours a day.

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Passive income

Many side hustlers would love to follow suit, dreaming of the day that their assets will generate enough income to support them. And it’s not necessary to own real estate to do it. Online platforms now make it simple to make money renting everything from your car to your lawnmower. Yet, where renting assets can be low-maintenance and lucrative, it pays to be cautious.

Host horror stories with Airbnb fill an entire web site. Some hosts complain about getting booted from the rental platform without appeal, having renters steal things, party or even commit suicide in a rental. Moreover, an increasing number of municipalities regulate and tax short-term rentals now. Airbnb’s “responsible hosting” page cautions hosts to be aware of local rules. Running afoul of the rules can lead to hefty fines.

Make money renting

Meanwhile, people who make money renting out other expensive assets sometimes complain about damage that’s not covered by insurance. Deductibles and exclusions can be substantial and unexpected.

Before renting out even something as incidental as your parking space, you ought to have a heart-to-heart talk with your insurance agent and your city’s permitting department. That can identify the hurdles and allow you to prepare before getting started.

What can you rent?

Rooms & vacation homes

The best known options for making money renting a room or a vacation home are Airbnb and VRBO. If you have a house in a well-traveled tourist area, you might also want to consider listing it on a specialized site, such as WeNeedAVacation  for Cape Cod/Nantucket rentals, for instance.

Event space or movie set

If you’re not sold on the idea of having overnight guests, you can also list your house, office or yard as an event space or movie set. What kind of event? Birthday parties, baby showers, corporate “team building” exercises, anniversary dinners, photo shoots — whatever your particular space lends itself to. Movie and advertising producers also regularly look for movie sets. This type of rental typically is booked by the hour or in 4-to-12-hour blocks. Sites that facilitate event rentals include Giggster, Splacer, and PeerSpace.

Sign up with Giggster here.


If you have spare wheels, you could make decent money renting the vehicle out to travelers through a site such as Turo. However, you don’t even need to let someone else drive to make money with your car. For instance, Giggster rents cars to be in the movies, and the owner gets to dictate whether the car can be driven by someone else. This can be particularly valuable for anyone who collects distinctive classic cars. And a variety of sites will also pay to rent the space on your car to advertisers. Wrapify, Carvertise and MyFreeCar all pay between $50 and $450 per month in exchange for plastering your car with (removable) advertising, while you drive as normal.


If you happen to have a watercraft, you can make big bucks renting it out through LakeHop, GetMyBoat or BoatSetter. (Of course, you’re already paying big bucks for the boat and its slip. So, this is more likely to defray your costs than make big money.) Large crafts are often rented out with the services of a captain, the cost of which you can fold into the rental rate. These two sites have different approaches to how they handle boat insurance. Make sure to pay attention and get a substantial deposit from all renters.


If you have a garage, driveway or dedicated parking space, and live in a densely populated urban area or near a stadium, restaurant or airport, you may be able to rent your parking space out too. Pavemint, CurbFlip and ParqEx all allow you to list your parking spot on their sites for pay.

Baby gear

If you’ve got kids and good-quality baby gear that you’re not currently using, you can rent that out through a site called BabyQuip. Parents who actively rent on the site earn an average of $600 per month, according to the site. But don’t sign up unless you’re pretty serious about renting your baby gear out regularly. This site requires a $100 “set-up” fee to get started and charges a commission on each rental and for liability coverage too. It is likely to require several rentals to break even.

Sign up with BabyQuip here.

Tools & Tents

Got a skill saw, nail gun, power-washer or carpet cleaner? Camping equipment or ski gear? You may be able to rent it out by the day or hour through FriendWithA or Loanables. All three sites let owners list their products for rent.

But, unless you have tools that are expensive and in high demand, this side hustle isn’t going to bring in big bucks. The typical tool rents for between $4 and $20 per day – not surprising given than many can be purchased for under $100. And you, of course, have to spend time meeting with the renters — as well as with your insurance agent. After all, you want to make sure you’re covered in the unlikely event that a renter hurts himself while using your chainsaw.

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