I'm doing my first timeshare rental. I've also arranged rentals from individuals that aren't timeshares (vacation homes). The advice that Denise linked to is good. I may have my own advice later (since we haven't used the timeshare yet, just arranged the rental).
Here's how I see it:
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Most people are good people. Well, maybe not totally good, but most people are not total scammers. In other words, if you just randomly rent from anyone, there's only a slim chance you'll get scammed. It's a good gamble.
- Do the things you can to try to prevent fraud (double checking your reservation by calling up the resort, paying with a method that leaves a trail, etc) but ultimately the best advice is:
don't spend more than you're willing to lose. Don't sign up for a rental that will leave you broke if things work out.
Also, renting from individuals means dealing with individual idiosyncracies. If you go to hotels.com and book a room it's simple and it's always the same. But when you rent from individuals you might get a chatty person who wants to email a lot back and forth or you might get someone who is tone deaf and doesn't get your jokes or you might get a worry-wart who wants you to sign some agreement that's 7 pages long. It's kind of interesting, really