I book a few properties a year on these platforms. Here's a long post on my tips. Most of the time things go perfectly fine so take all of this with a grain of salt, but I suggest doing your homework to protect yourself.
AirBnb and VRBO are the big 2 vacation rental sites. Many properties are listed on both sites and not always at the same price, always search both sites as the pricing usually varies. Make sure you review rental agreements, cancellation policies, and all-in pricing carefully, some prices are not shown during your search and only appear when you get close to checking out (e.g. taxes, cleaning fees). Sometimes the rental agreement may not be available before you book, in which case I'd suggest asking the owner/manager for it before you decide to book. The last thing you need is surprisingly brutal rental rules after you book a non-refundable deposit or fee. Cleaning fees and requirements can be quite high so make sure you understand these ahead of time. It's common for owners to ask that you take out trash, strip bedding, do dishes, etc. before you check out or they will tack on more fees for leaving the place "dirty." Renters are starting to push back on this practice since they see it as unjustly price increases, and hotels are seeing a bit of a resurgence as a result due to their no nonsense booking.
If the location you're renting in requires permits in order for an owner to rent the property, make sure it's permitted. Some locations will list this in the description especially if it's locale that is strict. Many will not and you may have to ask the owner to verify the permit info. Many areas do not require permits. Many unpermitted properties get booked every day in cities that "require" them. It's not always an issue but if the local city decides to crack down on a property after you book, or you have some issues during your stay, you're going to be screwed over because then it will surface that it wasn't a legal booking and you might get cancelled, kicked out, lose money, etc. and likely will have no recourse as the owner probably also lied to AirBnb/VRBO about having permits and the sites probably won't assist if that turns out to be untrue. How strict cities are varies widely. Mine states you need a permit but less than half of the properties here have one because owners don't want to pay for the permits, and 99% of the time nothing happens to unpermitted renters or owners here, but every locale is going to be different.
Beware if you see the same property listed multiple times on the same site for the same dates, usually would be under different names and might even have slightly different photos. A common scam is owners will keep listing a booked property to entice more renters at higher prices, and then they will cancel the cheaper booking. If that's you, you get screwed and probably won't get any help from AirBnb or VRBO and it might happen too late to find another good rental or hotel. Make sure you book a place not only with good reviews but a good quantity of reviews. You may see a place with few reviews offering a discounted price, it's up to you if you think it's worth the risk. I usually avoid anywhere without a lot of reviews unless it's the only option and in those cases I will do the max amount of research on the property and owners.
I tend to ask questions of the owners before booking even if I don't need much info, just to gauge their responsiveness and reachability (typically can only be done through the apps until close to your arrival). If they are flaky, not very responsive, it's a bad sign. If they ask you to communicate outside of the apps, run away and do not book. The backing companies of AirBnb/VRBO won't be able to see any offline messages and you won't have any protection from them if things go bad, all communications need to be through official channels.
Make sure you understand if you will be the only group and will have the property to yourselves, or if the owner is on site (sometimes in a separate part of the same home or in a separate home on the same property), or if other renters will be on the property or in the home or adjacent homes. Having others or the owner around is fine, just make sure you know what you are signing up for before you book.
I try to find the exact property location before booking. I might be the only one that does this level of research before I book though. The apps usually only give approximate locations, but with the property photos provided you can usually use google maps satellite and street views to find the exact location. The photos will typically have the front of the house or mailbox with the house number on it. If you get really lucky the photos will catch an unblurred street sign. There's almost always some distinguishing feature you can search for in Google maps even if you can't find a house number or street. You can use street view to get a sense of the surrounding neighborhood to see if it's clean, safe, etc. You may also want to look up crime stats for the exact area if you are concerned about the location.
I also tend to look up who is managing the property and I'll compare that to the property's public tax rolls to see if it matches up. If it's a property manager this often will not match, but if it's an individual it usually does. Google the names of the property managers or owners to see what you can find to make sure nothing looks strange. They'll have reviews on other booking sites for the same property or even other properties. Read them. A bad review for owners on other properties is a sign they may be a bad owner for the property you are looking at too. The names not matching tax rolls isn't necessarily a deal breaker but do your homework and do not book if something smells fishy.
The best pricing tip I can give you is if the listing is from a property manager, you'll almost always get better pricing booking through the property manager's website directly. VRBO and AirBnb have high listing fees which owners pass on to the renters. But make sure you understand the policies of anyone you book through first, if it's some hyper local property manager they may offer no protection if something goes wrong. For example, what happens if the property isn't ready, isn't available, or doesn't match the online description? What recourse do you have? Refund, rebooking (if so, where)? AirBnb and VRBO are kind of known for being owner friendly so if you as a renter have issues they may push back. Take photos, videos or whatever so you have evidence of your issues, if any. I like to do a property walkthrough upon arrival and immediately report any damage or issues, with photos, to the property manager so that I don't get accused of damaging it upon check out. Treat it like a rental car transaction, protect yourself for any existing damage upon your arrival.
Do not book with places that require you pay extra up front as a security deposit via paypal or check. You will have no way to get that money back if the owner decides to be a dick and accuse you of damaging something. This has happened to me, I lost $500 from an owner making up some story about damage that didn't exist and keeping my money, and VRBO wouldn't help me since it was my word vs. theirs. Now I only book at places that allow credit card payments and my preference is to book at places that offer damage insurance instead of a refundable security deposit. The insurance is usually pretty affordable and can cover thousands in damage. I've only ever needed the insurance once due to a small accident in a home, and it did it's job without costing me anything extra.
