Best Short-Term Rental Insurance Companies in Wisconsin (2026 Guide)

Choosing the right short‑term rental insurance for a Wisconsin property is one of the most important risk‑management decisions you can make as a host or investor. In this post, we’ll break down the best STR insurance companies for Wisconsin homes and clarify how products like Waivo, Safely, and RentalGuardian differ from true homeowners and landlord policies.​

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Why Wisconsin short‑term rentals need specialized insurance

Standard homeowners policies are usually designed for owner‑occupied primary residences, not income‑producing vacation rentals with a rotating cast of guests. When you regularly rent on Airbnb, Vrbo, or direct channels, stays are treated as a business exposure, and many traditional home policies either exclude or sharply limit that type of use.​

For Wisconsin hosts in markets like Door County, the Dells, and Northwoods lake cabins, that gap can become costly if:

• A guest is injured on your property and sues you.
• A fire or frozen pipe forces you to cancel weeks of bookings.
• A guest causes major damage to furniture, electronics, or finishes.

That’s why the best approach is usually a dedicated short‑term rental (STR) policy or a carefully structured combination of landlord insurance plus specialized guest‑damage coverage.​

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Best short‑term rental insurance companies for Wisconsin homes

While there’s no single “best” company for every host, several providers consistently stand out for Wisconsin STR properties.​

Proper Insurance

Proper Insurance is a national leader focused almost exclusively on vacation rentals. Instead of trying to patch your existing homeowners coverage, it replaces it with a commercial‑grade policy that treats your place as a lodging business.​

Key highlights:

• Building and contents coverage tailored for nightly rentals.
• Commercial general liability, often with higher limits than standard home policies.
• Business‑income coverage for lost bookings after a covered loss.

Proper tends to be a strong fit for full‑time or high‑revenue Wisconsin STRs, especially if you operate your property like a true hospitality asset.​

Steadily

Steadily is a dedicated landlord and short‑term rental insurer with specific products for Wisconsin properties. Its policies are built around the realities of Airbnb and Vrbo hosting, including frequent turnovers and guest‑caused damage.​

Why hosts consider Steadily:

• Clear coverage language for short‑term rentals.
• Landlord‑style protections plus guest liability.
• Options that work well for investors with multiple doors.

If you manage a portfolio of Wisconsin rentals or mix mid‑term and short‑term stays, Steadily can slot in nicely.​

CBIZ Vacation Rental Insurance

CBIZ Vacation Rental Insurance offers a comprehensive solution for owners who treat their STR as a business. The program is designed so that if the worst happens, you can rebuild and restore the property to operating condition.​

Typical features:

• Building and contents coverage at replacement cost.
• Liability protection for guest injuries and third‑party claims.
• Loss‑of‑income coverage for cancelled reservations following a covered claim.

CBIZ is often attractive to hosts who rely heavily on direct bookings and need clear, broad protection across channels.​

Wexford Insurance (Wisconsin‑focused broker)

Wexford Insurance is an independent agency with specific programs for Wisconsin Airbnb, Vrbo, and vacation rental owners. Instead of being a carrier itself, Wexford works with multiple specialty STR insurers to place you with the right fit.

Why this matters for Wisconsin:

• Agents familiar with Wisconsin property risks (snow load, frozen pipes, rural access).
• Clear guidance on why standard homeowners often excludes rental business use.
• Ability to compare several specialty carriers through one broker.

For local hosts who want a human who understands both Wisconsin and STRs, Wexford can be a strong first call.

NREIG (National Real Estate Insurance Group)

NREIG builds programs specifically for real estate investors, including Wisconsin rentals. Its structure works particularly well if you own multiple properties or vary usage between vacant, mid‑term, and short‑term.​

Core benefits:

• Portfolio‑style coverage for multiple properties.
• Premises liability (commonly 1M/2M limits) shared or per‑location.
• Month‑to‑month flexibility as properties change status.

If you’re growing a Wisconsin portfolio and want one scalable solution, NREIG is worth exploring.​

Mainstream carriers with STR endorsements

Some traditional carriers now offer short‑term rental options when usage is limited.

• Allstate: Has host‑oriented coverage (often called HostAdvantage or similar) that can be added to a homeowners policy to help with guest‑caused damage and theft.
• American Family (AmFam): Offers a specific temporary/short‑term rental coverage option when you rent your home for a limited number of days per year, extending many protections of your base policy to STR use.​
• American Modern: Provides coverage for homes rented out less than a few months per year, making it a fit for highly seasonal Wisconsin cabins.​

These can work well for “light” STR use—say, a primary or second home rented only during peak summer or holiday weeks.

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Waivo, Safely, RentalGuardian vs. homeowners insurance

One of the most confusing parts of insuring a short‑term rental is understanding how products like Waivo, Safely, and RentalGuardian relate to your base homeowners or landlord policy. They are not true replacements for homeowners insurance; instead, they sit on top as guest‑damage and liability solutions tied to each reservation.​

What Waivo, Safely, and RentalGuardian actually are

While the details differ by provider, Waivo, Safely, and RentalGuardian generally operate as programmatic guest‑damage and liability products integrated with your booking workflow.​

Common traits:

• Charged per booking or embedded in guest fees.
• Provide coverage for accidental guest damage to your property.
• Often include some level of guest liability protection.
• Designed to work across platforms, especially for direct bookings.

They’re highly useful tools, but they do not provide the full spectrum of protection you get from a homeowners or landlord/STR policy—especially for structure damage from non‑guest causes (like storms) and long‑term business‑income coverage.​

How Waivo‑type products differ from homeowners insurance

Here’s the core distinction:

• A homeowners or landlord/STR policy protects the building, your personal and business property, and your personal/enterprise liability against covered perils (fire, wind, certain water damage, etc.). It is long‑term, annual coverage designed to keep you financially whole when big losses occur.​
• Waivo, Safely, RentalGuardian protect you primarily against guest‑related risks attached to specific reservations—accidental damage, some liability, and in some cases additional theft or trip‑related coverages.​

In practical terms:

• If a guest breaks a TV or ruins a sofa, Waivo/Safely/RentalGuardian‑type coverage can respond quickly without forcing you into a major homeowners claim.
• If a lightning strike burns down the cabin, or a frozen pipe floods the main level in February, you still need a proper homeowners/landlord/STR policy for building and long‑term loss‑of‑income protection.

Think of Waivo, Safely, and RentalGuardian as high‑frequency, low‑to‑medium‑severity protection, while your base policy handles low‑frequency, high‑severity losses.​

Why you usually need both layers

For serious STR operators in Wisconsin, relying solely on a guest‑damage program is risky. Without an appropriate underlying property and liability policy:​

• You may have no coverage for major structure losses.
• You could face uncovered liability for non‑guest incidents (like a contractor injury).
• Your lender may consider you out of compliance with mortgage requirements that expect full homeowners or landlord coverage.

The most resilient setup is usually:

1. A dedicated STR or landlord policy (Proper, Steadily, CBIZ, NREIG, or a well‑endorsed mainstream carrier) that embraces rental use.
2. A Waivo/Safely/RentalGuardian‑type program layered on top to handle day‑to‑day guest damages efficiently and support direct‑booking operations.

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Comparing key options for Wisconsin hosts

Here is a high‑level comparison to help frame your choices.

Solution type	Examples	Primary role	Best use case in Wisconsin
Specialist STR policy	Proper, Steadily, CBIZ	Full building, contents, liability, business‑income	Full‑time/high‑volume STR and portfolios
Investor portfolio program	NREIG	Multi‑property, flexible status coverage	Owners with several WI rentals
Local STR‑savvy broker	Wexford Insurance	Places you with best STR carrier	Owners wanting local expertise and comparison
Mainstream carrier with STR add‑on	Allstate, American Family, American Modern	Light STR use built on homeowners policy	Primary/second homes rented seasonally
Guest‑damage & liability programs	Waivo, Safely, RentalGuardian	Reservation‑based guest damage and liability	Direct‑booking heavy or multi‑channel operators

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How to pick the right structure for your Wisconsin rentals

If you’re operating professionally, treat insurance selection like you would revenue management—structured and data‑driven.​

For each Wisconsin property, work through:

1. Use pattern
   • Full‑time or heavy STR: prioritize a dedicated STR policy (Proper, Steadily, CBIZ, placed via Wexford or NREIG).
   • Occasional rentals: explore American Family, Allstate, or American Modern endorsements aligned with your days rented.
2. Channel mix
   • Heavy direct bookings: consider pairing your base policy with a Waivo/Safely/RentalGuardian‑type program to standardize damage protection and claims across channels.​
3. Coverage priorities
   • Aim for replacement‑cost building and contents, at least 1M per‑occurrence liability, guest‑damage protection, and business‑income for lost bookings after covered events.
4. Local regulatory and lender requirements
   • Ensure the policy’s occupancy and usage wording matches how the property is actually used and any municipal or lender expectations.