Insurance & Protection
Proper Insurance
Comprehensive commercial coverage built for short-term rentals
Best Overall
The most comprehensive STR insurance — if you can stomach the premium
Contact sales • No free trial
Comparison
Proper 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: Proper Insurance or CBIZ Vacation Rental Insurance?
Pick Proper Insurance if you manage a mid-to-large portfolio, need STR-specific endorsements like squatter and amenity liability, or want the insurer VRBO exclusively endorses with Lloyd's of London underwriting. Pick CBIZ if you're a single-property or small-portfolio owner-host (1–4 units) who wants a straightforward bundled commercial policy from a broker with 20+ years in the vacation-rental niche.
Editorial perspective from the Proper Insurance side; factual claims about CBIZ Vacation Rental Insurance are drawn from its review.
Pricing Side-by-Side
Proper Insurance
Full pricing →Contact sales • No free trial
Contact sales
Custom quotes based on property location, size, usage, and rental frequency. Industry sources indicate STR-specific commercial policies typically cost 30–50% more than standard landlord coverage. No published rate card — contact sales for a quote.
Try Proper InsuranceCBIZ 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 Proper Insurance does well
Most comprehensive STR-specific coverage on the market
Proper offers unique protections like squatter coverage, amenity liability for bikes, kayaks, and hot tubs, bed bug remediation, and commercial general liability up to $2M — endorsements most competitors simply don't carry.
Strong claims handling with dedicated specialists
Policyholders consistently report smooth, professional claims experiences. One customer noted 'everything was handled quickly, professionally, with great communication, and the whole claims process was smooth and stress-free.'
Backed by Lloyd's of London and exclusively endorsed by VRBO
The Lloyd's underwriting (A.M. Best rated 'A' Excellent) provides financial stability, while the exclusive VRBO endorsement signals deep trust from a major OTA — a distinction no other STR insurer holds.
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 Proper Insurance falls short
Premium pricing that's hard to justify on thin margins
Multiple review sources call Proper 'one of the most expensive policies on the market.' Property managers note the premium can feel hard to justify until you actually need to file a claim.
No published pricing makes comparison shopping painful
Unlike competitors with posted rates, Proper requires a custom quote through their sales process. Operators evaluating multiple providers have to commit time to each conversation before seeing numbers.
Cancellation process can be frustrating
Some policyholders report friction when trying to cancel, particularly when taking a property off-market temporarily — a common scenario for seasonal STR operators.
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 Proper Insurance if
Large portfolio hosts needing comprehensive commercial coverage with specialized STR protections like squatter situations and amenity liability.
Skip Proper Insurance if
Budget-conscious operators or hosts with minimal rental activity seeking basic coverage.
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 Proper Insurance and CBIZ Vacation Rental Insurance actually differ
- Proper explicitly bundles squatter coverage, amenity liability (hot tubs, pools, watercraft), and bed bug remediation endorsements; CBIZ's default policy does not list these coverages.
- Proper underwrites portfolios of any size and is the largest STR-specific insurer in the U.S.; CBIZ caps eligibility at 1–4-unit residential properties, making it unsuitable for larger operators.
- Proper is underwritten by Lloyd's of London (A.M. Best 'A' Excellent) and is VRBO's exclusively endorsed insurance provider; CBIZ is backed by an A-rated carrier but lacks a comparable platform endorsement.
- CBIZ has been writing vacation-rental policies since 2002 — longer niche tenure than Proper — but has sparse independent third-party reviews compared to Proper's consistently positive policyholder feedback on claims handling.
- Proper is widely cited as one of the most expensive STR policies on the market; CBIZ pricing is undocumented but may be lower for simple 1–4-unit properties given its narrower endorsement scope.
Common objections
- CBIZ has been in the STR niche since 2002 — doesn't that longer track record matter?
- Tenure is real, but breadth of coverage is what pays out at claim time. CBIZ's longer history doesn't help if your policy excludes the specific risk that hits — squatter situations, bed bugs, or guest injury on an amenity. Proper's endorsement list is purpose-built for the scenarios standard and narrow STR policies leave uncovered.
- Proper is expensive — is CBIZ a cheaper way to get essentially the same protection?
- Not the same protection. Both are quote-only with no published rates, but Proper's higher premiums reflect broader endorsements and Lloyd's underwriting. If your property is a straightforward 1–4-unit listing without high-risk amenities, CBIZ's narrower policy may be adequate at a lower cost. If you have a hot tub, pool, or manage multiple units, the coverage gap matters more than the premium difference.
- I only have one Airbnb listing — is Proper overkill?
- It depends on your property's risk profile, not just the unit count. A single cabin with a hot tub and kayaks carries more amenity liability than a four-unit urban portfolio. Proper's coverage breadth protects against those scenarios; CBIZ may suffice for a simpler property. But if cost is the primary concern and your listing has minimal amenity risk, CBIZ is a reasonable alternative.
Keep Digging
Proper Insurance
The most comprehensive STR insurance — if you can stomach the premium
CBIZ Vacation Rental Insurance
Established specialty STR insurer — but you'll need to call for a quote