On VRBO (and perhaps others) there is an option to either pay $79 for an insurance policy covering $3000 in damage to the property or place a deposit for the same amount:

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Assuming that...

  1. The rental is within the next couple months and thus credit card dispute policy would still be possible
  2. You can afford to lose the use of that $3000 for a couple months

...is there any downside to saving the $79 and trusting that the credit card company will help you out with any disputes?

  • I think you've answered it yourself: the downside is having to trust the credit card company will take your side if you're in the right in a dispute. It's entirely possible that they won't investigate properly. – Nate Eldredge Apr 27 '15 at 14:47

The obvious downside is that if you do somehow manage to damage the property then some or all of your deposit will legitimately be withheld, whereas if you're insured the insurance should cover it (assuming the insurers don't wriggle out anyway).

As with any non-compulsory insurance product it's up to you to decide if the protection is worth the premium, given your perception of the risks.

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As mentioned in the comments, the question becomes whether you like dealing with your credit card company's dispute process or with the insurance company provided by the travel site. For myself, I've found that the credit card company takes more of a "we're on your side" stance than the insurance companies.

It's important to note also that this approach only works if you're booking within 60-90 days (depending on your credit card company's rules). Otherwise any dispute you have with the property owner will be too late to be handled by the credit card company.

Personal anecdote: I took this approach with our last vacation and saved the $79. The deposit was refunded and there was no need to dispute since there was no accident/damage while there.

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