Safely
Best for Small Hosts
Pick Safely if you're a low-to-mid occupancy host who wants pay-per-booking insurance bundled with proprietary guest screening (SafelyScore) and no annual commitment.
From $8 • No free trial
View alternativesAll tools/Awning Insurance
Insurance & ProtectionUpdated 2026-04-26
Awning Insurance
Curated STR insurance marketplace surfacing four vetted carriers
At a glance
Updated 2026-04-26Solid Option
Useful triage page for new Airbnb investors; thin if you already know the STR carrier landscape
Best for: First-time Airbnb investors who want a one-page triage of the four most-cited STR carriers without filling out four separate quote forms
Pricing
From $40 • No free trial
What Awning Insurance actually is
Awning Insurance is a curated short-term-rental insurance marketplace that routes hosts to four vetted carriers — Proper, Obie, Toggle, and Hippo — from a single landing page. It is a referral broker, not an underwriter: Awning publishes per-carrier price floors and one-line positioning so buyers can triage options without filling out four separate quote forms. The product sits inside Awning's broader investor toolkit (Airbnb estimator, management services), so the Obie path in particular is bundled into the same workflow investors already use to evaluate properties.
Core features
- Curated four-carrier comparison page (Proper, Obie, Toggle, Hippo)
- Published per-carrier price floors instead of contact-only quoting
- Embedded Obie quote workflow tied to Awning's Airbnb income estimator
- Coverage available in all 50 U.S. states
- Separate per-reservation policy ($36.72/reservation, up to 29 days) for managed properties
Pros
- Four named STR carriers compared on one page
- Transparent price anchors ($40/mo Obie, $100/mo Proper) instead of contact-sales gating
- Obie quote bundled into Awning's Airbnb estimator workflow
- Clear carrier-by-carrier positioning (luxury, budget, bundled, Airbnb-native)
Cons
- Awning is a broker — claims and renewals run through the underlying carrier
- Marketplace skips well-cited carriers like Steadily, Safely, CBIZ, and Farmers
- AM Best ratings and underwriter details are not surfaced on the marketplace page
- Page copy is Airbnb-centric; VRBO/direct-booking-only fit is unclear
Best for
- First-time Airbnb investors who want a one-page triage of the four most-cited STR carriers without filling out four separate quote forms
Not for
- Operators with commercial-zoned, international, or non-standard occupancy properties who need a specialized commercial broker
Is Awning Insurance right for you?
Honest per-segment take. Click any card for the full breakdown.
1–5 listings
Small portfolios
If you're a new Airbnb host evaluating your first STR policy, Awning's one-page comparison of four named carriers is exactly the triage tool you want.
Read full take →
5–20 listings
Mid-sized portfolios
Useful as a benchmark check against your incumbent carrier, but not a portfolio management tool — you'll still bind directly with one of the four partners.
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20–100 listings
Large portfolios
Awning's curated four-carrier set is consumer-facing residential STR; large portfolios with mixed property types should engage a specialized commercial broker directly.
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Airbnb primary
Airbnb-first hosts
Awning's marketplace copy is explicitly Airbnb-centric, and Proper is positioned as the most popular Airbnb-native STR carrier.
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Vrbo primary
Vrbo-first hosts
The marketplace doesn't speak to VRBO-specific underwriting needs; page copy is built around Airbnb hosting and AirCover.
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3+ channels
Multi-channel operators
The carriers themselves underwrite STR regardless of channel mix, but Awning's marketplace doesn't differentiate or guide based on multi-channel operations.
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Related tools
Same category, different fits. Each pick has a direct comparison reason.
Proper Insurance
Best Overall
Pick Proper Insurance if you need the most comprehensive STR-specific commercial coverage available — squatter, amenity liability, bed bug remediation, and up to $2M general liability — under a Lloyd's-underwritten policy that's exclusively endorsed by VRBO.
Contact sales • No free trial
View alternativesCBIZ Vacation Rental Insurance
Solid Option
Pick CBIZ if you're a U.
Contact sales • No free trial
View alternativesInsuraGuest
Best Value
STR 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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