Proper Insurance Review

Proper Insurance isn't a booking tool, a PMS, or an AI assistant — it's an actual insurance policy, built specifically to replace the homeowners or landlord policy that was never designed to cover a short-term rental in the first place. The company's own pitch is direct: standard homeowners policies exclude short-term-rental exposure outright, and the "home-sharing endorsements" some carriers bolt on typically add only about $10,000 of coverage for "$75-$100" a year — nowhere near enough if a guest gets hurt or a fire takes out the building. Proper sells a Lloyd's of London-backed policy instead, and says it's the exclusive preferred insurance provider named by Vrbo.

Pricing

Proper doesn't publish a rate card, a starting price, or even a sample premium anywhere on its site, and its own FAQ is upfront about why: "A dedicated STR policy like Proper's is priced for the actual risk profile of short-term renting," with cost depending on the individual property. The FAQ adds that because the policy replaces a homeowners policy rather than stacking on top of it, "many hosts find the total cost comparable, with substantially better coverage" — but that's a directional claim, not a number. Getting an actual figure means going through the "3 Minute Quote" link to portal.proper.insure, which we opened directly: it's a login screen (white-labeled "TopSail") asking for a username and password, with no pricing, tiers, or sample rates visible before you create an account. The FAQ itself confirms there's no instant checkout, telling applicants to "submit your information through our quote portal and we will be in touch with you." Coverage details compound the uncertainty: per the FAQ, "availability of coverage options, deductibles, discounts, and other policy features is dependent upon meeting underwriting guidelines and eligibility requirements," so even your deductible isn't fixed until underwriting runs. For a company that says it has written over 200,000 policies, that's a lot of gatekeeping between a visitor and a number — reasonable for a real insurance product, but worth knowing before you click through expecting a price.

Who it's for

Proper is built for hosts and owners treating a short-term rental as a real financial exposure, not a side hustle covered by a $75 endorsement. That includes full-time Airbnb and Vrbo hosts, rental arbitrageurs, and owners who split time between renting the property out and living in it themselves — the policy adds an extra $1,000,000 in personal liability specifically for that hybrid case. Commercial general liability starts at a $1,000,000 occurrence limit with $2,000,000 available, property is covered at replacement cost with no sub-limit on renter-caused damage (accidental, intentional, or malicious), and lost rental income is paid on an "actual loss sustained" basis with, per the site, no time limit on the payout. It's a weaker fit for anyone who wants to compare an instant online price against two or three other quotes in one sitting — Proper wants your information first, and a person follows up afterward.

What we could verify

We confirmed Proper Insurance Services LLC holds an A+ rating and has been accredited since August 12, 2015, per the BBB's own profile page. Proper's site states it has "over 200,000 policies written in all 50 states and Washington, D.C." and describes itself as a Lloyd's of London "Coverholder," a status it says only around 4,000 organizations worldwide hold — those are the company's own figures, not numbers we could independently audit. Proper's own testimonials page shows a run of recent 5-star reviews, several naming the same claims agent, Cali Sawinski, for fast bedbug and complex-loss settlements — a useful data point, but it's Proper's own curated page, not a neutral source. We tried to balance that with independent review-platform data: Proper Insurance isn't listed as a product on G2 or Capterra at all, and Trustpilot returned an HTTP 403 every time we tried to fetch its review page directly. That means we could not independently verify a review count or star rating for Proper on any of the three major platforms — a real gap in our research, not a number we're willing to guess at.

How it compares to our top pick

There's no real overlap between Proper Insurance and BnBGenius — they aren't competing for the same purchase decision at all. BnBGenius is a flat $10/month AI layer (free for your first 500 messages) that answers guest calls, creates cleaning and maintenance tasks, writes reviews, and pitches gap-night upsells, with no PMS required to run it. Proper is an annual insurance policy underwritten at Lloyd's that protects the building, its contents, and your liability if something goes wrong — it has nothing to do with guest messaging, turnover, or revenue management. A host could reasonably carry both at once: BnBGenius handling the day-to-day guest conversation, Proper covering the financial exposure if a guest gets hurt or a pipe bursts. If you're specifically shopping for STR insurance, Proper's Lloyd's backing, high liability limits, and Vrbo endorsement make it a credible name to request a quote from — just budget time for underwriting rather than expecting a same-day number. For the full field of AI messaging, PMS, and ops tools we've evaluated on the guest-facing side of hosting, see our best Airbnb host software ranking.