Buying a Vacation Rental, is it a big deal?

I'm going on vacation this weekend.  It's a mini vacation to an area that has condos that seem extremely affordable.  Is there a large barrier of entry to having a Vacation Rental By Owner and covering the costs of my vacation home?

Thousands of people utilize VRBO to list their vacation homes on the market.  Many people keep their vacation homes vacant throughout the year and miss out on a large opportunity to have their property pay for itself.

Many don't know that you can list your vacation rental online in front of millions of people, but you can also self manage it as well.  You can do this by utilizing a cloud based calendar for arrival dates, maintaining a detailed guest log book, and accepting payments all from the internet.

A 2015 Barclays report estimates that home rental platform Airbnb books around 37 million night stays, which could increase to as many as 129 million by 2016.  Most local governments are catching on, and it's important to check with your local ordinances to determine if you are complying to all tax laws.  

These websites like AirBNB and VRBO are not limited to vacations.  Many people are constructing small studio apartments on their property and renting them out short term to help pay for their mortgages.  Since these are short term rentals, it's important to have the proper insurance.  If you have a guest who causes damage, you need to make sure your policy will cover the cost.  

Since many of these properties are remotely managed, keyless entry is a must have.  Guests will expect a clean property upon arrival and having a trusted maid on call is very important.  For quick turn rentals, you'll need a quick turn cleaning service which could cost quite a bit of money.  If there are any issues with the property itself, a good handyman will be very valuable as well.

I'm hoping some of the folks here at biggerpockets will weigh in and let me know how their vacation rentals are going before I put my hat in the ring.