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 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: Proper Insurance or Awning Insurance?
Pick Proper Insurance if you need the most comprehensive STR-specific commercial coverage available — squatter, amenity liability, bed bug remediation, and up to $2M general liability — under a Lloyd's-underwritten policy that's exclusively endorsed by VRBO. Pick Awning Insurance if you want a one-page triage of four STR carriers (Proper, Obie, Toggle, Hippo) with published price floors before committing to any single quote process.
Editorial perspective from the Proper Insurance side; factual claims about Awning 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 InsuranceAwning 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 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 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 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 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 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 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 Proper Insurance and Awning Insurance actually differ
- Proper is the underwritten carrier (Lloyd's of London, A.M. Best 'A' Excellent) and is VRBO's exclusively endorsed STR insurer; Awning is a referral marketplace with no underwriting credentials and lists Proper as one of four partners from $100/mo.
- Proper writes commercial general liability up to $2M with squatter coverage, amenity liability (pools, hot tubs, bikes, kayaks), and bed bug remediation built in; Awning's marketplace page surfaces one-line positioning per carrier and doesn't expose comparable endorsement detail.
- Awning publishes transparent price anchors ($40/mo Obie, $100/mo Proper, $100–$200/mo typical bracket); Proper has no published rates, requires a custom quote through sales, and is widely cited as one of the most expensive STR policies on the market.
- Awning offers a separate per-reservation managed-property product at $36.72/reservation (up to 29 days) for guest-purchased coverage; Proper is exclusively an annual host-paid commercial policy with no per-booking option.
- Awning's curated set is four carriers and explicitly omits Steadily, Safely, CBIZ, and Farmers; Proper as a standalone option gives you direct access to dedicated claims specialists and an underwriter that 100,000+ STR policyholders already use.
Common objections
- If Proper is already on Awning's marketplace, why not use Awning to compare it against the other three carriers in one place?
- That's exactly Awning's pitch and it works for first-pass triage. The catch is that Awning surfaces one-line positioning, not endorsement detail or AM Best ratings, so you'll still click through to Proper's site to evaluate squatter, amenity, and bed bug coverage in any depth. If Proper is already your leading candidate, going direct skips the intermediary.
- Awning lists Proper at 'from $100/mo' — isn't that more transparent than Proper's contact-sales process?
- It's a useful price anchor but $100/mo is a floor, not a quote. Proper's actual premium varies significantly with property location, amenities, and limits, and is widely reported as one of the more expensive STR policies. Awning's number helps you bracket expectations; the real premium still comes from Proper's underwriting either way.
- Awning is consumer-facing and easy to use — why would I go through Proper's sales process instead?
- Because Proper is the policy, not the page. Awning's value is in surfacing four options quickly; Proper's value is the breadth of STR-specific endorsements and the Lloyd's underwriting that backs every policy. If you have amenities like hot tubs and pools or operate in markets where squatter situations are realistic, the sales-call friction is the price of getting those endorsements in writing.
Keep Digging
Proper Insurance
The most comprehensive STR insurance — if you can stomach the premium
Awning Insurance
Useful triage page for new Airbnb investors; thin if you already know the STR carrier landscape