At Proper, we always say that you never know the quality of your insurance, until you have to file a claim. As the nation’s leading insurer of short-term vacation rental properties, we have plenty of reviews to be proud of. We offer trademarked endorsements no other short-term rental carrier offers, and take pride in having the market’s most comprehensive vacation rental insurance program. Combine that with the backing of Lloyd’s of London, and you have over 100,000 satisfied policyholders.

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William Evans Avatar
A tornado destroyed our family vacation… A tornado destroyed our family vacation cabin May 6th, 2022. Proper Insurance stood by us throughout the process of rebuilding. The quality contractor they referred to us rebuilt our family cabin in about a year. This beat our expected timeframe for such a large project. We can't say enough good things about Proper Insurance and Chad Martin. Much appreciated. Evans Family
William Evans 1 week ago
Ren Little Avatar
I never thought I'd be so excited to write a review for an insurance company, but Proper has gone ABOVE AND BEYOND to work with me and my (very difficult) bank, and I honestly haven't had customer support this good maybe ever. Think high-end hotel or fancy-restaurant level care and service. I'd give them 6 stars if I could. Zach especially spent so much time working with me to fix an issue caused by an error that my bank made (and refused to fix), and ultimately he saved the day and got everything sorted out despite the bank refusing to fix its error. He was kind and patient and knowledgeable and helpful, and he knew how to advise me and how to ultimately go the extra mile to resolve the issue. From the beginning, Proper made it really easy and straightforward to get a quote, and even better, to UNDERSTAND the quote and what my coverage included. They specialize in insuring short-term rentals, and this being our first time owning a short-term rental property, we had a lot of questions, most of which were answered in our initial conversation and in the proposal they put together for us. The few other questions that I had come up as we were getting things set up, they had helpful answers for and were quick to respond. Also, they speak HUMAN, like I could actually understand what they were saying and they didn't use a lot of "insurance" jargon that normal people can't interpret. Amazing. To be fair, I haven't actually had to use the coverage yet for anything, but I feel so protected and good about the fact that if something does happen and we need it, we've got great coverage and even better, a trusted partner who will work with us and not try to make our lives difficult. Again, a big huge shout-out to Zach, I am SO grateful that I found Proper and will be recommending them to all of my short-term rental people!
Ren Little 1 week ago
Leo M Avatar
It was such a pleasure working with James Holen to get short-term rental insurance. The reviews for this company really do speak for themselves - the coverage is comprehensive, and seemed to be the best fit for our short-term rental property. James walked me through all the steps to apply for coverage, provided different options that would help bring down the premium, and processed the initial application really quickly through underwriting. I was really impressed with James, as he was really knowledgable about the policy and coverages, and wasn't trying to upsell me on anything. I really like that if I ever have a claim, he is the direct go-to person. Excellent customer service. Although I never hope to file a claim, I'm happy to know that I have this coverage and James would be on the case!
Leo M 1 week ago
June Pettigrew Avatar
storm damaged roof replaced! we had a storm with winds and hail. I contacted my Proper Insurance and was fortunate to get Chad to answer my call. He was so helpful! He quickly and efficiently walked me through the process to file a claim, get inspection and new roof completed in a prompt, professional manner. Chad was great with follow up for everything! A Pleasure to work with.
June Pettigrew 1 week ago
Amy Gurri Avatar
I tried to get home insurance which covered short-term rentals but found that most insurance companies in Connecticut won't cover short-term rentals and the ones that do have unreasonable requirements which would effectively negate any coverage. I then found Proper Insurance and talked to Jeff Heggem who made it really clear that this company specializes in short-term rentals coverage and really understands the business and potential risks. He walked me through coverage options and payment options. Once I applied, his extended staff helped me make sure the property was safe and ready for business. I haven't had a claim yet (and hopefully won't) but am sure the same efficiency and clarity will apply if it happens. I highly recommend Jeff and Proper Insurance.
Amy Gurri 2 weeks ago