Vacation Rental as a first time investment?

[Elie Jabbour]

I'm very eager to get started in real estate, but terrified of becoming trapped with a tenant horror story who doesn't pay rent and trashed the place prior to an eviction. 

I'm considering purchasing a beachfront condo and doing weekly rentals. Has anyone does this successfully as a first time investment? I have a HELOC that I plan to use as a down payment and trying to calculate a property where the return exceeds my mortgage & HELOC payments. Thoughts/advice?