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The first tip before you commit to a vacation rental, is to go deep on your research. That means, go beyond the owner's description and photos and read the the reviews. Like with Yelp, you can throw out extreme critiques and figure the truth lies in the amalgam of reviews.
Further, go beyond the rental site by going to Google and pulling up the street view of the potential rental. This will give you a realistic view of the locations,, the exterior of the property, and a look at the surrounding neighborhood.
Go through the listing with a fine tooth comb. Is this a stand alone property? Or is a guest house in the backyard or a flat that adjoins the main house? The wording can be deceptive so make sure you have clarity before booking.
If you're unsure of anything, communicate with the owner. A responsive owner is one that's generally engaged with their property. Ask questions, make sure this is a good match.
Be sure you understand all the surcharges. Some rentals require insurance which could add a significant chunk to your total expense. If you want an earlier check in or late check out, that might cost extra too. Your rental home may come with a swimming pool, but if you want it heated, it could mean an extra $50 a day.
Also, note the cleaning fee. They fluctuate dramatically and could be a deciding factor if you're only renting for a quick weekend getaway. The service fee on Airbnb in particular, can be surprising.
Make sure you understand the cancellation policy. Some can be quite punitive and may be the deal breaker in your final decision. Never wire money, always pay by credit card.
Finally, avoid vacation rentals on Craigslist. Scam artists have been known to copy legitimate rentals and post them on Craigslist, only to take your deposit and run.