The first property we ever rented in Orlando, Florida
1. Check out average hotel prices for the area first. Although I have rarely come across a place where rental properties are more expensive than hotels, there are some exceptions. Always best to do your research so you don't end up paying more than you have to.
2. Make sure you check out the rules in the area around rental properties. There are some areas that have regulatory authorities that don't allow short term rentals. It could be specific to a building, or it could be specific to a geographic area. A simple google search should bring up linked to a specific geographic location. As for buildings, that's a little trickier. Check the listing and see if the person listing is asking you not to interact with security in the building, or if they ask you to say you are a "friend of the owner". Chances are, they aren't supposed to be renting their place.
3. Read reviews. This one is a big one. If a property has no reviews and there is very little information about the property owner/manager, that's a big red flag. Sometimes new properties offer some great deals, but without reviews, there isn't a lot of information about what you could be getting.
4. Not all reviews are created equal, so read between the lines. If a property only has 3 reviews, but they all appear to say almost the exact same thing, red flag. We're all different, so they should all appear to be written by different people in style, not just name.
If there are negative reviews, be sure to pay attention to what they are complaining about. Are the complaints about paint colour? The cable package? Are those things that will ruin a trip for you? However, if the complaints are about things like mold, or other safety concerns, you may want to rethink renting it.
5. Consider whether rental properties are right for you. While rental properties can have a lot of positives, it depends what you like. Hotels have staff. Perhaps a concierge to help you make reservations. They may have a steady stream of cabs available to take you where you want to go. Airport shuttles. Security guards. These are some examples of things you may be giving up by going with a rental property. So it's important to outline what you need in your rental. If you can't find a rental property that has what you want, then maybe a hotel is better for what you need.
My rental in August 2016 in Quebec City