John,
VRBO…Expensive, for super popular vacation rental areas, has a client base that has more money and is looking for nicer accommodation. Can opt to use VRBO Reservation Manager = AWESOME vacation rental workstation manager
Airbnb…Inexpensive, "hipster" version of VRBO, takes a fee off the reservation, has a younger clientele that is looking for good deals
I believe your situation might be better suited for Airbnb though. VRBO would be good to have as well, you'd just have to keep up on updating both calendars/spend for both.
You also need to look into your state's taxes…In Hawaii where my rental is located we not only have to pay GE tax but the "hotel" TAT Transient Accommodation Tax" which both total to about 14%!
As far as managing a vacation rental goes, you'll find the nicer the place you have the better people leave it. When guest stay at a nice place they'll think "hey this guy is on top of it" meaning the owner will be on top of any deductions from the damage deposit…After a year of vacation renting I've found the most trouble you'll get is broken kitchenware or dings in the wall. It's tough to screen a guest but if you charge a premium you'll usually get older more responsible guests…
Key to making a vacation rental work is to ensure your reviews are near perfect, your cleaners are reliable and understand you run a mini hotel, your customer service is excellent, always be available for questions and respond quickly, offer more amenities then the competition, set up systems to where you have "canned" email response, rental agreements, check-in instructions, condo/local area info book/powerpoint! http://www.vrbo.com/426946
Best of luck man!