Proper Insurance vs Safely

Proper Insurance sells a single annual policy that fully replaces your homeowners or landlord policy with a commercial short-term rental policy, custom-written with Lloyd’s of London and Concert Specialty. It combines homeowners, landlord and business insurance in one contract, covering the building, contents, business income and liability — and critically, it covers the property whether it’s currently rented, sitting vacant, or being used by you or family, closing the occupancy gaps that trip up standard homeowners policies used for STR.

Safely flips the model: each reservation gets its own per-booking policy, so you pay only when guests are actually staying, layered on top of your existing homeowners coverage rather than replacing it. That means no ongoing annual premium for vacant periods, but also means you need your own homeowners policy to remain in force for the gaps Safely doesn’t cover. Neither structure is objectively better — it’s a question of your occupancy rate and whether you want one all-in-one policy or a supplemental per-stay layer.

Proper’s annual premiums typically range $1,000–3,000/year for a single-family STR, varying with property value, location, amenities and risk features — a fixed cost regardless of how many nights you actually book. For a property running 70%+ occupancy, that fixed cost usually works out cheaper per booked-night than an ongoing per-stay fee.

Safely’s per-booking model runs roughly $4–10 per night when annualized, though actual quotes are property-specific. For a seasonal cabin booked 100 nights a year, that’s $400–1,000 total — potentially far less than Proper’s flat annual premium, since you’re not paying for the vacant months. Neither company publishes simple flat-rate pricing, so getting quotes from both against your actual booking calendar is the only way to know which is genuinely cheaper for your specific property.

Safely integrates guest screening directly into its per-booking product — every reservation gets screened as part of the same workflow that issues the policy, adding a layer of risk filtering beyond what insurance alone provides. For hosts who want fewer separate tools, this bundling has real operational value.

Proper Insurance is a traditional insurance product with no built-in screening or booking automation — you’ll need a separate tool (Autohost, SuperHog, or your PMS’s native screening) if guest vetting matters to your risk management. This is consistent with Proper scoring lower on automation and integrations in our rubric (6/10 and 3/10 respectively) — it’s excellent insurance, not an operations platform.

Proper’s policy includes extensive enhancements: guest-caused damage and theft, liability for pets, liquor, pools, hot tubs, bikes and recreational areas, ordinance-or-law coverage for building limits, and bed bug coverage with lost-income protection — a genuinely comprehensive list built specifically around STR risk scenarios.

Safely covers up to roughly $1,000,000 in structural damage or bodily injury per stay, plus around $10,000 in contents damage or theft — including intentional damage and, in some programs, bed bugs. Coverage limits are customized in both cases, so review the actual policy documents rather than marketing summaries; "up to $1M" and "custom quote" both mean you need to read the fine print before assuming either covers your specific worst-case scenario.

Proper Insurance covers all 50 US states plus DC. Safely is similarly US-centric, with best availability and terms for US-based properties and managers. Neither is a fit for hosts outside the US — if that’s you, look at region-specific alternatives (regular landlord insurance with an STR endorsement, or a specialty broker in your country) rather than either of these.