Great for
First-time Airbnb investors who want one comparison page for Proper, Obie, Toggle, and Hippo without filling out four separate quote forms.
Solid Option
Last updated 2026-04-26Awning Insurance Review: Is It Worth It?
Our independent take on Awning Insurance from an STR operator lens. No sponsored placements. From $40 • No free trial.
Our verdict
Useful triage page for new Airbnb investors; thin if you already know the STR carrier landscape
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.
What we like
Four named STR carriers compared on one page
Awning surfaces Proper, Obie, Toggle, and Hippo with one-line positioning each, cutting the search-and-compare burden for buyers who don't already know the STR-insurance landscape.
Transparent price anchors instead of contact-sales gating
The marketplace publishes 'rates starting at just $40/month' for Obie and 'From $100/month' for Proper, plus an affordability bracket noting most hosts pay $100–$200/mo for comprehensive coverage.
Obie quote bundled into the Airbnb estimator workflow
For investors already using Awning's Airbnb income estimator, the Obie partnership lets them request a quote in under 5 minutes from inside the same workflow used to underwrite the property.
Clear carrier-by-carrier positioning
Toggle is steered to high-value/luxury (custom limits up to $2M+), Hippo to bundled homeowners+STR, Obie to budget, and Proper to Airbnb-native — useful triage without reading four carrier sites.
Where it falls short
Awning is a broker, not the carrier
Claims, renewals, and underwriting run through whichever partner carrier you bind with. Awning's own roundups describe its row as 'Coverage Limit: Varies' and the unique feature as 'Integrated with PM platform' — positioning is integration, not underwriting.
Curated set excludes carriers Awning's own editorial recommends
The marketplace omits Steadily, Safely, CBIZ, and Farmers, even though Awning's STR roundup highlights CBIZ as specializing in rental property insurance and Farmers for first-claim forgiveness — creating editorial-vs-marketplace inconsistency.
AM Best and underwriter details not on the marketplace page
Awning's per-reservation product page only says it 'can connect hosts with multiple different insurance companies depending on the property' without naming an underwriter, forcing buyers to click through to each partner site to verify carrier financial strength.
First-party pricing URL is missing
The dedicated /str-insurance/pricing path returned 404 on 2026-04-26, so all pricing has to be extracted from marketing copy on the marketplace landing page rather than a canonical pricing URL.
Is Awning Insurance right for you?
OK for
Mid-portfolio operators (3–10 listings) with an incumbent carrier who want a quick benchmark quote to validate that current pricing is reasonable.
Skip if
You run commercial-zoned units, international properties, or non-standard occupancy — Awning's curated set is U.S.-only and skewed toward residential single-family Airbnb use.
Pricing in one line
From $40 • No free trial
Awning is a referral marketplace — the platform itself is free; cost is the underlying carrier premium. Published floors: Obie from $40/mo, Proper from $100/mo. Awning's own affordability bracket says most hosts pay $100–$200/mo for comprehensive STR coverage. Per-reservation managed-property product is a separate $36.72/reservation guest-purchased policy.
See full pricing breakdown →Ready to try Awning Insurance?
There's no free trial, so ask the sales team for a walkthrough before committing.
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