Insurance & Protection
Awning Insurance
Curated STR insurance marketplace surfacing four vetted carriers
Solid Option
Useful triage page for new Airbnb investors; thin if you already know the STR carrier landscape
From $40 • No free trial
Comparison
Awning Insurance vs Safely
Pricing, pros and cons, and buyer-fit side-by-side. Pick the one that matches your operation — or see why neither should.
Insurance & Protection
Safely
Pay-per-booking vacation rental insurance with built-in guest screening
Best for Small Hosts
Best pay-per-booking insurance for low-to-mid occupancy hosts
From $8 • No free trial
✓Editorial verdict
Which Should You Pick: Awning Insurance or Safely?
Pick Awning Insurance if you're a first-time Airbnb investor who wants a one-page triage of four annual STR carriers with published price floors before quoting. 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.
Editorial perspective from the Awning Insurance side; factual claims about Safely are drawn from its review.
Pricing Side-by-Side
Awning Insurance
Full pricing →From $40 • No free trial
Obie
From $40/mo
- Budget-friendly part-time and full-time host coverage
- Quote completion in under 5 minutes via Awning estimator integration
Proper
From $100/mo
- Airbnb-native integration with flexible coverage
- Fast underwriting; positioned as the most popular STR carrier
Toggle
Custom (high-value properties)
- Custom limits up to $2M+ for luxury vacation rentals
- White-glove claims service
Hippo
Competitive (bundled)
- Combined homeowners + STR coverage under one policy
- Digital-first claims for part-time rental hosts
Safely
Full pricing →From $8 • No free trial
Safely Protection Policy
$8/night
Estimated $800-$1,200/year per property depending on occupancy
Any; pay only when bookings occur
- Up to $1M primary commercial damage coverage
- $10K contents protection
- No monthly commitment; activates per-booking
- Bundled guest screening at $0.50/night
Guest Screening (standalone)
$5 per check
Drops to $0.50/night when bundled with Protection Policy
Any
- Access to SafelyScore guest database
- Identity verification
- Cross-reference against vacation-rental damage history
- Stand-alone option without full insurance coverage
Enterprise / Custom
Custom quote
Multi-property portfolios
- Everything in Protection Policy
- Volume pricing based on property count and location
- Custom deductible choices
- Dedicated account support
What each tool does well — and where it falls short
What Awning Insurance does well
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.
What Safely does well
Proprietary SafelyScore database screens guests against actual vacation rental damage history
No other platform has a comparable industry-specific damage database. Screening also covers criminal databases, sex offender registries, and Interpol/Europol watchlists.
98% of claims paid in 4.5 days with sub-$1K claims within 24 hours
Operators document damage with photos and receipts — no guest confrontation required. Homeowners have up to 60 days to file.
Zero cost during vacancy with insurance fees passable to guests
Coverage activates at check-in and deactivates at check-out, eliminating traditional damage deposit friction. Operators build the fee into the nightly rate so guests effectively cover the insurance.
Where Awning Insurance 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.
Where Safely falls short
Per-night pricing compounds quickly at high occupancy
At 200+ nights/year the per-night model can exceed annual policy costs from competitors like Proper Insurance ($1,500–$2,500/year). Operators must calculate their breakeven.
Does not replace homeowners insurance and has meaningful coverage exclusions
Excludes weather damage, non-guest-caused damage, fine art and collectibles. Contents theft/damage caps at $10,000 and there is a 90-day maximum consecutive rental period.
Limited public reviews and relatively new market presence
Compared to established insurers like Proper Insurance or CBIZ, Safely has fewer independent user reviews, making real-world claims experience harder to assess at scale.
Which Should You Pick
Pick Awning Insurance if
First-time Airbnb investors who want one comparison page for Proper, Obie, Toggle, and Hippo without filling out four separate quote forms.
Skip Awning Insurance 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.
Pick Safely if
Seasonal or part-time hosts renting fewer than ~100 nights/year who want insurance and guest screening bundled without an annual commitment — the pay-per-booking model keeps costs proportional to actual occupancy.
Skip Safely if
You run high-occupancy properties at 250+ nights/year — per-night pricing will exceed annual policy alternatives, and coverage caps ($10K contents, no weather damage) may be insufficient for premium properties.
Where Awning Insurance and Safely actually differ
- Awning is a referral marketplace pointing to four annual carriers (Proper, Obie, Toggle, Hippo); Safely is a pay-per-night product starting at $8/night with zero cost during vacancy and no annual policy commitment.
- Safely bundles guest screening via its proprietary SafelyScore damage-history database at $0.50/night when paired with insurance; Awning is pure carrier referral with no guest-screening component on either its marketplace or per-reservation product.
- Safely integrates natively with Hostaway, Guesty, Hospitable, and Lodgify for automatic per-booking activation; Awning has no documented PMS API, Zapier listing, or webhook for its insurance product.
- Safely publishes claims metrics (98% of claims paid in 4.5 days, sub-$1K claims in 24 hours); Awning is a broker — claims and renewals run through whichever underlying carrier you bind with, and Awning doesn't surface claims-handling data on its marketplace page.
- Awning's separate managed-property product is a $36.72/reservation guest-purchased policy (up to 29 days); Safely's per-night model also passes through to guests via the nightly rate but caps stays at 90 days and excludes weather damage and fine art.
Common objections
- Why use Awning's marketplace when Safely already gives me per-booking coverage plus guest screening in one product?
- If pay-per-booking and bundled screening are what you want, Safely is shaped for that and Awning isn't — Awning's four partners are all annual policies. Awning is a triage tool for hosts choosing between annual carriers; Safely is the answer if you specifically want per-night coverage without a yearly commitment.
- Safely integrates with my PMS and activates per booking — does Awning have anything comparable?
- No. Awning has no documented PMS integrations, API, or Zapier presence for its insurance marketplace; it's a consumer-facing referral page. If automated per-booking activation inside Hostaway, Guesty, Hospitable, or Lodgify is a workflow requirement, Safely is the right shape and Awning is not.
- Awning lists $40/mo Obie and $100/mo Proper — isn't that cheaper than Safely's $8/night?
- It depends on occupancy. Safely's per-night model favors hosts under roughly 100–150 nights/year; above that, the per-night cost compounds past what an annual policy would run. Awning's anchors give you the annual bracket up front, but you're still on annual coverage with no guest-screening bundle. Run your expected nights against both before assuming the cheaper sticker wins.
Keep Digging
Awning Insurance
Useful triage page for new Airbnb investors; thin if you already know the STR carrier landscape
Safely
Best pay-per-booking insurance for low-to-mid occupancy hosts