Pick Awning Insurance if you're a first-time Airbnb investor who wants a one-page triage of four annual carriers (Proper, Obie, Toggle, Hippo) with published price floors before starting any quote process.
From $40 • No free trial
View alternativesAll tools/Safely
Pay-per-booking vacation rental insurance with built-in guest screening
At a glance
Updated 2026-04-19Best pay-per-booking insurance for low-to-mid occupancy hosts
Best for: Seasonal or part-time hosts renting fewer than 100 nights per year who want insurance and guest screening bundled without an annual commitment
Pricing
From $8 • No free trial
Safely is a pay-per-booking vacation rental insurance provider that bundles property damage protection (up to $1M primary commercial coverage, $10K contents) with guest screening powered by SafelyScore — a proprietary database of guests who have caused damage at other vacation rentals. Coverage activates at check-in and deactivates at check-out, so operators pay nothing during vacancy. Costs can be passed through to guests as a fee built into the nightly rate.
Honest per-segment take. Click any card for the full breakdown.
1–5 listings
Safely's pay-per-night model is built for you — zero cost during vacancy, no annual commitment, and guest screening bundled in.
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5–20 listings
Safely can work across a 10–30 unit portfolio, but run the occupancy math — per-night pricing may exceed annual alternatives at scale.
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20–100 listings
Pay-per-booking math works at high nightly-rate properties but gets expensive at 250+ nights/yr/property. Large operators running high-occupancy urban or resort units often do better with annual policies like Proper or Steadily at this scale.
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Airbnb primary
Safely supplements AirCover with real commercial insurance and a faster claims process, but you're already getting some baseline protection from Airbnb.
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Vrbo primary
Vrbo's damage protection is weaker than Airbnb's AirCover, making Safely's supplemental coverage more valuable — but the same cost math applies.
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3+ channels
Safely works across channels, but verify PMS integration support for your stack before committing — the full integration list is not publicly confirmed.
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Same category, different fits. Each pick has a direct comparison reason.
Pick Awning Insurance if you're a first-time Airbnb investor who wants a one-page triage of four annual carriers (Proper, Obie, Toggle, Hippo) with published price floors before starting any quote process.
From $40 • No free trial
View alternativesPick Proper Insurance if you need the most comprehensive commercial STR coverage available — squatter protection, amenity liability, bed bug remediation, and up to $2M in general liability under one policy.
Contact sales • No free trial
View alternativesPick CBIZ if you need a full commercial replacement policy with business-income protection and broader coverage for a dedicated STR property you operate year-round.
Contact sales • No free trial
View alternativesSTR operators on a connected PMS who want a low-flat-rate guest-damage and accidental-medical layer they can pass through as a guest fee.
From $69 • No free trial
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