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
Comparison
CBIZ Vacation Rental Insurance vs Proper 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
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
✓Editorial verdict
Which Should You Pick: CBIZ Vacation Rental Insurance or Proper Insurance?
Pick CBIZ if you're a U.S. owner-host of 1–4 STR units who wants a bundled commercial policy from a broker with 20+ years of niche tenure. Pick Proper Insurance if you need the broadest STR-specific endorsements — squatter, amenity, and bed bug coverage — backed by Lloyd's of London and exclusively endorsed by VRBO.
Editorial perspective from the CBIZ Vacation Rental Insurance side; factual claims about Proper Insurance are drawn from its review.
Pricing Side-by-Side
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 InsuranceProper 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 InsuranceWhat each tool does well — and where it falls short
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.
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.
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.
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.
Which Should You Pick
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.
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.
Where CBIZ Vacation Rental Insurance and Proper Insurance actually differ
- Proper explicitly covers squatter situations, amenity liability (hot tubs, pools, watercraft), and bed bug remediation; CBIZ's published policy description does not mention these endorsements.
- CBIZ is eligibility-capped at 1–4-unit residential properties; Proper is the largest STR-specific insurer in the U.S. and underwrites portfolios of any size.
- Proper is underwritten by Lloyd's of London (A.M. Best 'A' Excellent) and is VRBO's exclusively endorsed STR insurer; CBIZ is backed by an A-rated carrier but has no comparable platform endorsement.
- CBIZ has underwritten vacation-rental policies since 2002 — longer niche tenure than Proper — but has lower market visibility.
- Both are quote-only with no published rates; Proper is widely cited as one of the most expensive STR policies on the market, while CBIZ pricing is undocumented and tied to property amenities, location, and coverage limits.
Common objections
- Proper has VRBO's exclusive endorsement and Lloyd's underwriting — isn't CBIZ a step down in credibility?
- Proper has the stronger visible credentials, but CBIZ has been writing vacation-rental policies since 2002 — longer than Proper has existed — and is backed by an A-rated carrier. If platform endorsements and carrier name recognition matter to you, Proper wins. If niche broker tenure matters more, CBIZ holds its own.
- I manage 15+ units across an LLC — can CBIZ even cover me?
- Probably not under a single policy. CBIZ's program is built around 1–4-unit owner-host properties, not large portfolios or property managers. Proper underwrites larger portfolios and is the better fit for multi-property operations — this is one of the clearest differentiators between the two.
- Both require a phone call for a quote — is one process easier than the other?
- Neither publishes rates. CBIZ's pricing page returned a 404 as of April 2025 and directs you to a phone/form workflow. Proper also requires a custom quote but is more widely discussed online, so you're more likely to find ballpark cost references from other hosts before you call.
Keep Digging
CBIZ Vacation Rental Insurance
Established specialty STR insurer — but you'll need to call for a quote
Proper Insurance
The most comprehensive STR insurance — if you can stomach the premium