In the example above, part of signing the contract is agreeing that your usage of the vehicles doesn’t involve reselling them. Signing that contract with intent to re-rent them is a very clear legal problem.
There are several other layers of problems. When you rent something to someone else, you are representing that you have legal standing to rent it out.
If you rent out someone else’s property after agreeing to a contract that says you cannot rent it out, you are doing some more serious misrepresenting of the key facts and your intent. It could also trigger laws about theft of services depending on the situation.