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
Comparison
Safely vs Awning Insurance
Pricing, pros and cons, and buyer-fit side-by-side. Pick the one that matches your operation — or see why neither should.
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
✓Editorial verdict
Which Should You Pick: Safely or Awning Insurance?
Pick Safely if you want pay-per-booking coverage that activates at check-in, bundles proprietary SafelyScore guest screening, and integrates natively with Hostaway, Guesty, Hospitable, and Lodgify. 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.
Editorial perspective from the Safely side; factual claims about Awning Insurance are drawn from its review.
Pricing Side-by-Side
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
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
What each tool does well — and where it falls short
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.
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.
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.
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.
Which Should You Pick
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.
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.
Where Safely and Awning Insurance actually differ
- Safely is a pay-per-night product starting at $8/night with zero cost during vacancy and no annual commitment; Awning is a referral marketplace routing buyers to four annual carriers with floors of $40/mo Obie and $100/mo Proper.
- Safely bundles guest screening via its proprietary SafelyScore damage-history database at $0.50/night when paired with insurance; Awning has 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 — and is the underwriter-facing brand; Awning is a broker, so claims and renewals run through whichever partner carrier you bind with and no claims-handling data is surfaced on the marketplace.
- 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
- Awning lets me compare four named carriers on one page — why pick Safely instead of just shopping the marketplace?
- Awning is built for triage between annual carriers (Proper, Obie, Toggle, Hippo) and that's genuinely useful if you're new to STR insurance. But Safely solves a different problem: pay-per-booking coverage with proprietary guest screening bundled in. If per-night pricing and SafelyScore screening are what you want, none of Awning's four partners are shaped for that.
- Awning publishes price floors at $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, per-night costs compound past what an annual policy would run. If you book 250+ nights/year, an annual carrier through Awning will likely be cheaper on insurance alone — but you'd still be paying separately for any guest-screening tool.
- Safely is supplemental and caps contents at $10K — wouldn't a full commercial policy from one of Awning's carriers be more comprehensive?
- Yes, on coverage breadth. Proper through Awning writes commercial general liability up to $2M with squatter, amenity, and bed bug endorsements that Safely doesn't include, and Toggle handles luxury limits up to $2M+. Safely is intentionally supplemental and per-stay; if you need a primary commercial policy that covers the property year-round, Awning's marketplace points at the right shape of product.
Keep Digging
Safely
Best pay-per-booking insurance for low-to-mid occupancy hosts
Awning Insurance
Useful triage page for new Airbnb investors; thin if you already know the STR carrier landscape