Has anyone used airbnb or a similar application and can share their experiences? I'm thinking of planning a trip and I don't want to worry about booking hotels in advance. Any advice would be appreciated!

Yes, don't do it if you have a condo to share. If you must, make sure you post roommate wanted. According to condo law you cannot rent out a position of your unit. But there is no law about roommates.

Read your condo docs carefully