We have 2 rentals in Cambridge, MA, which is a city that is very similar to Oakland. We rent both apartments during the academic year by the semester or full year term. Then during the summer, we rent one on the "sublet" market for 3 months because it is in a condo association building and we don't want to be annoying to the other residents. We generally have to take a hit on the rent during the summer because there is a glut of summer sublets available in Cambridge. The other one is on the first floor of our 2 family house. So we rent it as a vacation rental on Airbnb and VRBO/HomeAway. We have had great experience with vacationers but I think it has helped that we are here to greet each guest as they arrive and it doesn't hurt that we live upstairs. We pay $70 to have the apartment thoroughly cleaned between each visitor and we add this fee to the reservation total. We also put out fresh flowers and a high end chocolate bar on each pillow.
I was very concerned originally that we'd have guest who weren't happy with our busy urban neighborhood. But perhaps because we emphasize we are in the midst of a hopping urban environment, we've had no complaints from any of our guests. We generally get 5 star reviews from our visitors.