Get as much information from the people that you are dealing with and be sure that they are reputable. Ask for references and do a little research.
If you are dealing with an owner directly, you can search the Collier County Tax Records to verify ownership.
If it is a really great rental and worth some time & effort -
See if you can find feedback for the person/group handling the rental somewhere. Ask them for references that you can call and talk to. If they are a company call the local chamber or BBB to see if there are complaints or if they are actually part of the community.
Our recommendation is to be very careful with these dealings. You are certainly within your rights to request the rentor to provide proof of their identity and ability to collect these funds.
Craigs List patrons have been exploited in situations like these....proceed with caution.
I own a small brokerage firm in Naples that does a fair number of rentals. I would have you speak with my rental specialist, Cathy Graves, who is, I believe, one of the best rental agents in Naples. You can call her direct at 239-404-0650 or log onto our rental website : http://exceptionalrentals.us. There is a lot of information on the website about what to expect, etc.
If you rent through a realtor, you are getting protection of your deposit, because it has to be held in an escrow account. If you rent through an individual you don't know, you are taking more risk.
Broker-Owner, Exceptional Properties of SW Florida
I'm not saying that this is a scam, but would not say this is norm, nor reccomend paying all upfront. I personally would not pay upfront and if I can help you with giving you a name and number of a rental management company I would be happy to. If it is a nationaly known company like orbitz, then they may have insurance coverage for your trip. Then, I would think it is OK ,but please be careful with craigslist and trust. It is an awsome site but open for deception. Like I said if I can help I would be happy to.