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 CBIZ Vacation Rental 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
CBIZ Vacation Rental Insurance
Specialty STR insurance for U.S. owner-hosts
Solid Option
Established specialty STR insurer — but you'll need to call for a quote
Contact sales • No free trial
✓Editorial verdict
Which Should You Pick: Awning Insurance or CBIZ Vacation Rental Insurance?
Pick Awning Insurance if you're a first-time Airbnb investor who wants a one-page triage of four named STR carriers (Proper, Obie, Toggle, Hippo) with published price floors before talking to anyone. Pick CBIZ if you're a U.S. owner-host of a 1–4-unit STR who wants a true commercial policy with up to $2M aggregate / $1M per-occurrence liability and business-income coverage from a broker with 20+ years of niche tenure.
Editorial perspective from the Awning Insurance side; factual claims about CBIZ Vacation Rental Insurance 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
CBIZ Vacation Rental Insurance
Full pricing →Contact sales • No free trial
Contact sales
Quote-based pricing only — premiums vary by property amenities, location, and coverage limits. CBIZ does not publish rate cards; the vendor pricing path returned 404 on 2026-04-25 and the product site directs prospects to a phone/form quote workflow.
Try CBIZ Vacation Rental InsuranceWhat 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 CBIZ Vacation Rental Insurance does well
Specialty commercial coverage that replaces a homeowners policy
CBIZ markets a single bundled policy covering dwelling, contents, liability, and business income for STR use — addressing the property-damage and liability gaps that platform-provided host policies and standard homeowners policies typically exclude.
High commercial liability limits available
Policies are written with up to $2 million general aggregate and $1 million per occurrence, suitable for owners with pools, hot tubs, or watercraft amenities that drive higher liability exposure.
A-rated carrier with deep tenure in the niche
CBIZ has been insuring vacation rental properties since 2002 and the current national program is backed by an A-rated insurance carrier, per the 2025 program-relaunch press release.
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 CBIZ Vacation Rental Insurance falls short
No published pricing — every prospect must request a custom quote
Buyers cannot comparison-shop on the website; the vendor pricing URL returned 404 on 2026-04-25 and the product site routes all inquiries through a phone/form quote workflow.
Limited independent third-party reviews
Public review platforms have sparse coverage of CBIZ customer experiences — Awning explicitly notes that no third-party online reviews exist for this established provider, making independent verification difficult.
Coverage gaps in specialty risks
Liquor liability, squatter coverage, pet/animal liability, and earthquake are not included by default — operators with bars, exotic pets, or West Coast properties may need supplementary policies.
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 CBIZ Vacation Rental Insurance if
U.S.-based individual owners of single-family, condo, or 1–4-unit short-term rental properties who want commercial-grade liability and property coverage to replace a homeowners policy.
Skip CBIZ Vacation Rental Insurance if
You are a property manager seeking PMS-side software integrations, a buyer who needs transparent published premiums, or you operate outside the United States.
Where Awning Insurance and CBIZ Vacation Rental Insurance actually differ
- Awning is a referral marketplace surfacing four vetted carriers (Proper, Obie, Toggle, Hippo) with published floors of $40/mo Obie and $100/mo Proper; CBIZ is the underwriting broker itself with no published rates and a phone/form intake at 855.945.5221.
- CBIZ writes a single bundled commercial policy (dwelling, contents, liability, business income) with up to $2M aggregate / $1M per-occurrence liability; Awning doesn't underwrite anything — coverage limits depend entirely on whichever partner carrier you bind with.
- CBIZ explicitly covers amenity risks like pools, hot tubs, and watercraft that homeowners policies exclude; Awning's marketplace page doesn't surface amenity-liability detail and forces a click-through to each partner site to verify.
- Awning's curated set explicitly omits CBIZ — even though Awning's own STR editorial roundup highlights CBIZ as specializing in rental property insurance — creating a marketplace-vs-editorial inconsistency.
- CBIZ has been writing vacation-rental policies since 2002 and is backed by an A-rated carrier; Awning's marketplace page doesn't surface AM Best ratings or underwriter detail for any of its four partners.
Common objections
- Awning has four carriers on one page — why call CBIZ for a quote when I can comparison-shop in minutes?
- Awning is good for triage, but it's a broker page that hands you off to whichever carrier you click. CBIZ is the underwriter and writes a true commercial STR policy with $2M aggregate liability and business-income coverage that none of Awning's four partners are positioned to match without comparable endorsements. If you want commercial-grade coverage rather than the cheapest sticker price, the phone call is the trade-off.
- If Awning's own editorial recommends CBIZ, why isn't CBIZ in their marketplace?
- It's a fair question and the inconsistency is real. Awning's marketplace surfaces only the four partners it has referral relationships with (Proper, Obie, Toggle, Hippo), not the carriers its editorial guides recommend more broadly. If CBIZ is the right shape for your property, you'll need to go direct — Awning won't route you there.
- I want transparent pricing before I talk to anyone — doesn't Awning win on that?
- Yes, on price anchors specifically. Awning publishes $40/mo Obie and $100/mo Proper floors plus a $100–$200/mo affordability bracket. CBIZ has no published rates and routes every prospect through a custom quote. The honest call: if a published floor is your top filter, start with Awning; if you need a real commercial policy with $2M liability and amenity coverage, the CBIZ quote process is unavoidable.
Keep Digging
Awning Insurance
Useful triage page for new Airbnb investors; thin if you already know the STR carrier landscape
CBIZ Vacation Rental Insurance
Established specialty STR insurer — but you'll need to call for a quote