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 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: Safely or Proper Insurance?
Pick Safely if you're a seasonal or low-occupancy host who wants pay-per-booking insurance bundled with guest screening and no annual commitment. Pick Proper Insurance if you need the most comprehensive commercial STR coverage available — squatter protection, amenity liability, bed bug remediation, and up to $2M in general liability under one policy.
Editorial perspective from the Safely side; factual claims about Proper 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
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 InsuranceWhat 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 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 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 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 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 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 Safely and Proper Insurance actually differ
- Safely uses pay-per-night pricing starting at $8/night with zero cost during vacancy; Proper Insurance requires a custom-quoted annual premium with no published rates.
- Safely bundles guest screening via its proprietary SafelyScore damage-history database at $0.50/night when combined with insurance; Proper is pure insurance with no guest-screening component.
- Safely offers primary commercial coverage up to $1M with a $10K contents cap; Proper offers commercial general liability up to $2M with Special Form Coverage for building and contents.
- Proper covers squatter situations, amenity liability (pools, hot tubs, bikes, kayaks), and bed bug remediation — none of which Safely includes.
- Safely is supplemental coverage that does not replace homeowners insurance and excludes weather damage and stays beyond 90 days; Proper is a standalone commercial policy designed to be your primary STR coverage.
Common objections
- Proper Insurance covers way more risks — why would I settle for Safely's supplemental coverage?
- If you rent fewer than 100–150 nights per year, Safely's per-booking model will cost significantly less than an annual Proper policy, and you get guest screening bundled in. Most low-occupancy hosts never encounter squatter situations or bed bug claims — you're paying Proper's premium for coverage you may never use.
- Safely's $10K contents cap and coverage exclusions seem like serious gaps compared to Proper.
- They are real gaps. If you own premium-furnished properties or have high-liability amenities like hot tubs and pools, Proper's broader coverage is the right call. But for standard vacation rentals with typical furnishings, $10K contents plus $1M liability covers the vast majority of realistic damage scenarios — and Safely's 98% of claims paid in 4.5 days means you actually get the money fast.
- Proper is backed by Lloyd's of London and endorsed by VRBO — can Safely match that credibility?
- No, and we won't pretend otherwise. Proper has deeper market tenure, more public reviews, and the Lloyd's underwriting is a genuine mark of financial strength. Safely is a newer entrant with fewer independent reviews. The tradeoff is flexibility: no annual commitment, pay-per-booking pricing, and built-in guest screening that Proper doesn't offer.
Keep Digging
Safely
Best pay-per-booking insurance for low-to-mid occupancy hosts
Proper Insurance
The most comprehensive STR insurance — if you can stomach the premium