Short-Term Rental Insurance Providers: What Owners Should Compare Before Choosing Coverage

Owner Protection Stack

ASTRO does not sell insurance, endorse any provider named here, or receive compensation for provider examples. This article is educational only—not insurance, legal, tax, or financial advice. Provider names, categories, and coverage details are research starting points that change frequently; confirm everything against each provider’s current materials and your own written policy. ASTRO records what protects your property; it never decides it. No policy, product, or provider is required for membership, verification, the registry, or the Owners Exchange.

There are dozens of companies that will sell a short-term rental owner “protection.” They are not the same kind of thing. Some are regulated insurance policies. Some are damage-protection products that are not insurance at all. Some are booking-platform benefits that exist only while a guest is booked through that one platform. Choosing well starts with knowing which is which.

A cap quoted in an article is stale the day the product page changes. A cap confirmed in writing at purchase is coverage.

This guide is the comparison companion to the five-layer insurance protection stack. That guide describes the layers every owner should understand. This one helps you choose between the companies that sell them. When you have made comparisons, write them into the coverage worksheet so next year’s you can see what this year’s you confirmed.

The three-way distinction, and who you buy it from

There are three kinds of protection: a Policy, a Waiver, and a Platform benefit. A Broker is not a fourth kind — it is one way to buy the first. Four questions sort any company, and nearly every confusion in this market comes from comparing across these categories as if they were interchangeable.

Badge legend used below: Policy · Broker (places you with a carrier) · Waiver (protection product, not insurance) · Platform (channel-specific). A company can wear more than one badge; when it does, that is the first thing to untangle.

Policies & brokers — regulated coverage, and who places it

A Policy is written by a regulated carrier that stands behind the claim. A Broker does not insure you itself—it shops carriers and places you on one of their policies. Both belong here because both put you on regulated insurance; the difference is who you are actually buying from.

Proper Insurance Policy

Proper positions its short-term-rental policy as a commercial business policy meant to replace an inadequate homeowner or landlord policy—building, contents, business income, and commercial general liability on one form, available in all 50 states per its materials.

Ask:

• Does this fully replace my homeowner or landlord policy, or sit alongside it?
• What building, contents, liability, and loss-of-income limits apply—and what is excluded?
• Are direct bookings and vacant periods covered the same as OTA bookings?
• Who owns this provider today, and who is the actual carrier or paper behind the policy?

Owner translation: Compare Proper against Steadily and CBIZ when you want a single dedicated STR policy rather than patching a homeowner policy with endorsements. A related company, Waivo (per public materials), sells a damage waiver—a useful reminder that two products from the same house can sit in two different categories.

CBIZ Vacation Rental Insurance Policy

CBIZ has insured vacation rentals for years and, per its materials, relaunched a National Vacation Rental Insurance Program backed by an A-rated carrier. Treat any older CBIZ description you find online as potentially stale and read the current program terms.

Ask:

• Is the offered policy the current national program, and who is the A-rated carrier?
• Are STRs, long-term rentals, second homes, and vacant periods each treated differently?
• Are guest injury, owner contents, amenities, and loss of income all included?
• What optional endorsements exist, and which are required for my property?

Owner translation: Compare CBIZ against Proper when you want a vacation-rental-specific program with a long track record; the deciding detail is the current policy form and carrier, not the brand’s history.

Steadily Policy

Steadily provides landlord and short-term-rental coverage across all 50 states as a dedicated rental-insurance provider, with damage and liability for Airbnb- and Vrbo-style rentals down to nightly stays, per its materials. It frames the property as an investment asset — and, as with any provider, the carrier actually writing the paper is worth confirming.

Ask:

• Is this a true STR policy, a landlord policy, or a landlord policy with STR permissions?
• Are direct bookings, furnishings, and loss of business income covered?
• What happens to coverage during vacant periods between stays?
• Who is the carrier writing the policy behind the quote?

Owner translation: Compare Steadily against Proper and Obie when you think of the property as an investment and want a modern quote flow—but confirm “rental property” on the quote actually means “short-term rental business.”

Obie Broker

Obie is an insurance marketplace/broker for landlords and investors—it places you with third-party carriers rather than being the carrier itself. The quote page is not the policy; the carrier and form behind it are.

Ask:

• Is Obie acting as a broker or a carrier in this transaction, and who is the actual insurer?
• Does the placed policy explicitly permit short-term rental use, direct bookings, and vacancy?
• What endorsements are required, and what STR-relevant exclusions apply?

Owner translation: Compare Obie against going direct to Proper, CBIZ, or Steadily when you want one broker to shop multiple carriers—the value is the comparison, but the coverage still lives in whichever carrier’s form you end up on.

InsuraGuest Policy

InsuraGuest offers, per its materials, a primary, no-fault hospitality-liability product delivered as a property-level subscription that sits in first-dollar position—paying on covered in-stay incidents without first forcing a claim against your own homeowner policy. It is narrower than a full property or business-income policy and is meant to complement, not replace, core coverage.

Ask:

• Is this primary and no-fault, and exactly which in-stay incidents does it cover?
• Does it replace any part of my core property or liability policy, or only sit in front of it?
• How is it priced, and does coverage depend on a PMS integration being active?

Owner translation: Compare InsuraGuest against a damage waiver when you want a first-dollar, no-fault layer for in-stay incidents—but pair it with a core property policy, because it is not one.

Safely Policy

Safely pairs an insurance-backed protection policy with a guest-screening layer—the policy can reach high commercial limits per its materials (structural, contents, guest-caused damage, and bodily injury), and the screening is prevention that feeds it. Read it as a Policy with a prevention layer bolted on, not two separate purchases.

Ask:

• Am I buying screening only, the protection policy only, or the bundle?
• What does the protection policy actually cover, and what are its limits and exclusions?
• Does protection depend on every guest being screened first, and what happens if one fails?
• Does it apply to direct bookings, and what guest data is collected?

Owner translation: Compare Safely against Truvi when you want prevention and a backstop from one vendor; the deciding question is whether the insurance half is broad enough to lean on, or just a supplement to a core policy.

Damage-protection products — not insurance

Waivo Waiver

Waivo is a vacation-rental damage-protection product—a security-deposit replacement that reimburses guest-caused damage (accidental and, per its materials, intentional damage and theft) with no deductible. It is a stay-level layer, not a property policy, and—per public company materials—it is affiliated with Proper as a sister company.

Ask:

• Is this insurance, a waiver, or a reimbursement service—and who is protected?
• What is the per-stay limit, and does it cover contents and building damage or only guest-caused loss?
• Does it apply to direct bookings and OTA bookings alike?
• What proof and what deadline are required to be reimbursed?

Owner translation: Compare Waivo against a security deposit and against Truvi when you want first-dollar guest-damage recovery without holding deposits—but it does not replace core property insurance, and never treat it as if it does.

RentalGuardian (Home Guardian / Home Guardian+) Waiver

RentalGuardian is a damage- and liability-protection administration platform; “Home Guardian” and “Home Guardian+” are its protection-plan tiers (they are product tiers, not a rebrand of the company), and—per public materials—it sits within the Inhabit group. Confirm the exact current tier, limits, ownership, and administering agency on the live product page before relying on any figure—these change.

It also administers guest-facing trip protection in some booking flows, so identify which product you are actually buying.

Ask:

• Which tier is being offered (Home Guardian vs Home Guardian+), and who administers and underwrites it?
• Is this damage protection, liability protection, trip protection, or a bundle?
• What are the current limits and exclusions—confirmed on today’s product page, not last year’s?
• Does it require the guest to buy or accept anything, and does it apply to direct bookings?

Owner translation: Compare RentalGuardian’s tiers against Waivo and Truvi when the protection will sit inside your booking or PMS flow—the deciding detail is the current tier’s limits and who administers claims, which is exactly the kind of fact worth confirming in writing.

Truvi (formerly Superhog) Waiver

Truvi—the company formerly known as Superhog—combines guest screening, ID verification, and a damage-protection guarantee with claims paid directly, tiered per its materials. It is a risk-management product, not a traditional insurance policy, and it emphasizes direct-booking risk management.

Ask:

• Is the product screening, damage protection, claims support, or a bundle?
• Does protection apply only after a guest is screened, and what is the per-stay damage limit?
• Which booking channels and which PMS integrations are supported?
• What documentation is required for a claim, and who pays it?

Owner translation: Compare Truvi against Safely and Waivo when you want screening plus guest-damage protection for direct bookings; because it spans prevention and protection, insist a vendor say plainly which half you are relying on for a given incident.

Platform protections — channel-specific, not a substitute

Airbnb AirCover for Hosts Platform

AirCover for Hosts bundles host damage protection and a host liability insurance component, governed by Airbnb’s terms and applying only to stays booked through Airbnb. Airbnb itself states it is not a replacement for a private policy.

Ask:

• Does it apply to this specific reservation, and what are the deadlines and exclusions?
• Is this damage protection, liability insurance, or both—and what proof is required?
• How does it interact with my own policy, and does anything apply outside Airbnb?

Owner translation: Compare AirCover against your own policy, not against another provider: it can help on eligible Airbnb bookings and does nothing for direct bookings, off-platform repeat guests, or vacant nights.

Vrbo Host Protections Platform

Vrbo provides a liability-insurance component for eligible reservations—generally structured as excess over the host’s own policy—plus accidental-damage-protection options. Per its materials a deductible may apply if your personal insurance does not contribute, and the liability program does not cover damage to your own property.

Ask:

• Does the liability protection apply to this reservation, and is it primary or excess?
• Did the guest purchase accidental-damage protection, and what limit and deadline apply?
• Does a deductible apply if my own insurer does not contribute, and does anything apply outside Vrbo?

Owner translation: Compare Vrbo’s program against your own policy the same way: it is channel-specific and excess, so a direct booking or an off-Vrbo stay carries none of it.

How to compare, once you know the category

Within the right category, compare on the axes that actually decide a claim—not on headline marketing:

• Underlying insurance vs waiver. Is a regulated carrier on the hook, or is this a contractual guarantee that can decline outside its narrow terms?
• What is covered. Property peril, liability, business income/loss-of-rents, contents, amenities, and guest-caused damage are five different things—confirm each, not “covered” in the abstract.
• Exclusions and conditions. Business use, undisclosed amenities, vacancy, pets, parties, and intentional acts are where coverage quietly ends.
• Direct-booking applicability. Does the protection follow the property, or only certain channels?
• Channel dependence. Platform benefits lapse off-platform and while vacant—map every way a guest can book.
• Claims handling. Who files, by when, with what proof, and who actually pays?
• Written-confirmation questions. Anything a salesperson says that is not on the policy form is not coverage.
• Material-change triggers. See the next section—these silently break last year’s comparison.
• State and product availability. Programs, tiers, and caps vary by state and change without notice.

Material-change triggers

Any one of these can silently void the comparison you did last year—because it changes the risk your existing coverage was priced for:

• Adding an amenity (pool, hot tub, dock, golf cart, fire pit).
• Allowing pets.
• Launching direct bookings or a new channel.
• Increasing occupancy or adding events.
• Renovating or changing the property’s use.
• Transferring the property to an LLC or trust.
• Adding or changing a property manager.

The fillable twin of this list lives in the coverage worksheet’s change-trigger sheet. When one of these happens, re-confirm coverage in writing—do not assume the old answer still holds. Provider ownership and product tiers change; the questions do not.

Why this matters for ASTRO owners

ASTRO is built for short-term rental owners, and it keeps a property’s record separate from the shifting products layered on top of it. Insurance, waivers, and platform terms all change on their own schedules; the property, and the durable record of it, do not. ASTRO records what protects your property; it never decides it. No policy, product, or provider is required for membership, verification, the registry, or the Owners Exchange. A registry identity is not an insurance policy, listing-control verification is not liability coverage, and Owners Exchange settlement does not insure the building. What ASTRO gives you is a stable place to stand while you compare the coverage that is genuinely yours to choose.

The Simplest Counterargument

Most owners will never file a catastrophic claim, and comparing a dozen providers across nine axes is real work for a risk that may never arrive. Buying the cheapest adequate policy and moving on is a defensible choice, and this guide’s framework can feel like overkill for a single, simple property.

That objection is fair. What still holds is that the cost of comparing is paid once, in an afternoon, while the cost of discovering a category mistake is paid at the worst possible moment—after a loss, when the “protection” you counted on turns out to have been a platform benefit that lapsed, or a waiver that never covered the peril. You do not need every layer. You do need to know which category each thing you are paying for belongs to.

What breaks when owners get this wrong

• A platform benefit (AirCover, Vrbo) is treated as the property’s insurance—and a direct booking or vacant night is uninsured.
• A damage waiver is mistaken for a policy—and a fire, a liability claim, or lost income falls into a gap it never covered.
• A homeowner or landlord policy is assumed to permit nightly rentals without written confirmation—and business use is excluded at claim time.
• A cap read in an old article no longer matches the current product page—and the owner is under-covered by a number that changed.
• An amenity, pet, or entity change is never disclosed—and a material-change trigger quietly voids the coverage.
• The company that pays the claim turns out to be a different entity than the website that sold it—because “who backs it” was never asked.

The worst time to learn which category your protection belonged to is after the claim.

Related owner reading

• The Owner Protection Stack — how insurance fits with prevention, deposits, and association rules as one system.
• The 5-layer short-term rental insurance protection stack — the layers this guide helps you shop for.
• The coverage worksheet — write your comparisons down so they do not go stale in your head.

Educational information only—not insurance, legal, tax, or financial advice. Provider categories, coverage, limits, ownership, and availability change; confirm current terms directly with each provider and read your own policy form before relying on any coverage.