My husband and I have been using VRBO and AirBnB to travel around the country for the last 7 months. We have travel booked in San Antonio, TX for Jan-April 2016, New Orleans for May 2016.
We are now planning our next legs of travel and have found two VRBO properties... one in Maine for June-August 2016, and another in Boone, NC for Sept-Nov 2016. I have not booked these properties yet nor have communicated with the owners. However, on their "Book it" details, they are asking for either 50% of the entire rental at the time of the reservation, or 100% of the reservation at the time of the rental.
I want to rent this far in advance to make sure I have a good selection of properties to rent, but I am worried about making such a big financial commitment that far in the future. They both have 100% money-back guarantees if I cancel 30 days prior to check in, but that is not my worry. I am worrying about what if they cancel on me, and I cannot get my money back from them. It is my understanding that VRBO releases the money to the owner within 5 to 7 days after the money is paid as opposed to holding the money for release until the renter checks in.
I have looked at the various trip insurances that VRBO offers, but none seems to apply to me. Their "Cancellation Protection" policy protects me if I am the one that cancels but does not apply if THEY cancel on me and I have trouble getting a refund. The "Carefree Rental" seems to be for rentals not as advertised.
My main concern is that I rent far in advance, pay the money up front, the owner gets their money. Then, if I need to cancel or they sell the property, etc, and I request a refund and they don't return my money, what is my recourse? Has anyone had any experience with this. I have used VRBO and AirBNB and have had no problems whatsoever and have been very happy with it, but I have never rented this far in advance.
Thank you very kindly for any insight into this situation!

If you are going to rent in a vacation focused area with a limited season - such as Maine - they will often require you to make a substantial payment up front since they are taking a significant risk by taking the property off the market. (For examples, summer house rentals for the Hamptons typically have to be paid by Feb or March and there are often significant penalties if you cancel - up to 100% if you wait until late April or early May to cancel.)

Obviously any of the things you are worried about might happen - although they don;t seem likely. But you are getting the benefit of locking in the property you want in a high volume area - and this seems like the risk you need to take to do this.

However, since these are lengthy rentals it seems like if there is a problem you could take the owners to small claims court - which obviously wouldn;t make sense for a rental of only a couple of nights.

For rentals of such a long period you might consider going through a regular summer rental agent - so there is a responsible third part you can deal with.

Our only experience with a late owner's cancellation was a fire. It was four weeks out and the deposit was quickly refunded. My initial thought was that they got a better offer. But a quick check of the local newspaper did show a fire at that address. It does cause a lot of problems because of airline tickets and no replacement at that late date. There was never any question about the refund of deposit and it was through VRBO in the Keys.

I agree with nytraveler, you have to decide whether it's worth the small risk of someone cheating you to reserve the property you want.

I probably wouldn't worry too much about it, however, a listing that looks like it's been around for a while (as evidenced by the number and age of comments) would make me feel better.

We have several times put 50 or 100% deposits on properties through both vrbo and air bnb. We have never had trouble, but yes, there is a risk involved, I suppose.

One time with vrbo we negotiated with the owner to pay a smaller deposit, I think $300 and then six months out the rest of the first half and then the rest 60 days out. You can always try to negotiate.

I know that air B and B collects the money and releases it. With vrbo and home away I have always paid owners directly, some by credit card. In that case it can be taken up with the card company I suppose.

I think this has evolved because people would reserve more than 1place; shop around; and then at the last moment would cancel. Plenty of people do that with hotel rooms, so doing it with house rentals (especially during prime season) would be the next step. It's less likely done when you have to pay 50% etc.

Rentals are a step of faith, on both parties. Each has the potential to lose out.

It's not unusual to have to pay half or all the rental cost. Several rentals on VRBO now accept credit cards. Using the credit card protects you.
I have purchased trip insurance through TravelGuard to cover vacation rentals.

If you "have to" cancel, trip insurance should cover it, if you are talking about having a medical problem suddenly, husband dying, etc. that's what it is for. There are zillions of travel insurance companies, no reason to buy from VRBO who doesn't insure everything, they aren't an insurance company.

As for fraud or someone not returning your money due, you'd have to sue in small claims court, just like anything else. Not easy to do from afar, that's for sure, but VRBO is really just an advertising website. They just aren't an agency nor do they want to get involved being a lawyer or consumer advocate for the thousands of owners advertising on their website.