Oh, ok. Didn't understand the question. I actually think that they are talking about a hurricane preventing you from going, as compared to the villa itself being destroyed, as I'm sure that is a standard clause in all of their bookings. My GUESS is that if the villa is uninhabitable, they would transfer you to a different villa or give you your money back. But travel insurance is always a good idea. Be aware however that there is a huge difference between "cancel for any reason" insurance, and insurance that covers cancellation because of a specific reason, like a hurricane, or a medical condition or because your proposed accommodation is unavailable because of hurricane damage. Cancel literally for ANY reason is very expensive to get, as it literally means you could cancel if you decided you just didn't want to go anymore.
Travel insurance is very individual to your particular risks. As with any insurance, the devil is in the details. For example, stuff like coverage for medical issues may or may not cover your particular problem. Let's say your travel partner gets sick. The cancellation insurance would mostly like kick in. But what happens if your mother becomes very ill and she's not travelling with you. You don't want to go because she is in hospital and could pass away and you know you will not be able to enjoy yourself.
You may or may NOT be able to use the cancellation policy then, depending on what the actual terms of the policy say.
So, what we do is to determine what particular risks I think are my biggest concerns. Since we're older, we ALWAYS get medical evac coverage when we go to the Caribbean, because medical care is not the best, anywhere in the Caribbean. And your personal insurance may or may NOT cover you in network in the Caribbean. So, if you're out of network, your co-pay may be 50%. For us, we're on Medicare and Medicare has ZERO coverage in the Caribbean, except in the USVI. Now, we have a Medicare Supplement policy, but it only covers 80%. 20% can be a huge number, when you're talking medical bills. Now, if your personal insurance covers you exactly the same down island as in the States, then your situation is different. Which is what I'm saying, what are YOUR biggest risks that you want to insure against.
Another question in your situation is whether you might be better purchasing two different policies for the two very different trips. We purchase our travel insurance through TTOL sponsor Insure my Trip. You perhaps should contact them on the phone and ask that question, about whether it would be better to purchase two different policies.
Otherwise, it's very easy to just go to their website--through the link here on TTOL--and see what particular risks you want to insure against. If you use the link here, then if you purchase through them, TTOL gets a small commission.
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