5 Best Short-term Rental Insurance Companies | Fit Small Business

5 Best Short-term Rental Insurance Companies

Whether you’re a snowbird who rents your home out periodically or a rental homeowner who rents out the property for an extended time, you need vacation rental insurance. We reviewed over a dozen insurers using our proprietary rubric and determined the five best short-term rental insurance companies: How I Evaluated the Best Short-term Rental Insurance…

Written By
Sophia Doyle
Sophia Doyle
May 6, 2026
7 minute read

Whether you’re a snowbird who rents your home out periodically or a rental homeowner who rents out the property for an extended time, you need vacation rental insurance. We reviewed over a dozen insurers using our proprietary rubric and determined the five best short-term rental insurance companies:

CompanyBest for
Foremost InsuranceOverall for vacation rental insurance
ObieShort-term rentals
CBIZHomes with amenities like a pool
American FamilyRenting out a vacation house
SafelyGuest screening or property management

How I Evaluated the Best Short-term Rental Insurance Companies

To determine which insurance company is best for you, I used a proprietary in-house evaluation system. I reviewed over a dozen of the best vacation rental insurance companies and presented the five with the highest scores.

In evaluating insurance companies, I focused on the customer’s needs. I paid particular attention to convenience, financial ratings (from AM Best), customer service, the types of policies offered, and the overall experience as a policyholder with a specific provider.

Best Vacation Rental Insurance Companies Compared

CompanyQuote ProcessPolicy Purchase ProcessAccessibilityAdditional ServicesFinancial RatingOverall Score
Foremost InsuranceThrough an agentThrough an agent24/7 call centerApp for policy and claims servicesA (Excellent)4.31
Get a quote from Foremost Insurance
ObieOnline or over the phoneOnline or over the phoneMonday to Thursday, 9 a.m. to midnight Eastern time
Friday, 9 a.m. to 11 p.m. ET
Risk map to help with purchasing a propertyA+ (Superior)4.25
Get a quote from Obie
CBIZStart online and finish over the phoneThrough an agentMonday to Friday, 8 a.m. to 5 p.m. Central timeProperty management resourcesA+ (Superior)4.06
Get a quote from CBIZ
American FamilyThrough an agentThrough an agent24/7 call centerOnline policy servicesA (Excellent)4.06
Get a quote from American Family
SafelyOnline or over the phoneOnline or over the phoneMonday to Friday, 9 a.m. to 5 p.m. ETGuest screeningA (Excellent)3.93
Get a quote from Safely
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Foremost Insurance: Overall Best for Vacation Rental Insurance

To obtain a quote, you will need to speak directly with an agent.

Foremost offers a landlord policy for your vacation or short-term rental needs. If you want to insure a second home, the carrier also offers a seasonal policy that does not have a primary residence requirement.

For vacation rentals, check out the landlord and vacation rental policy. Whether you rent out your home rarely or every other weekend, the policy has no cap on the frequency of rentals. The only stipulation is that the property cannot be rented to the same tenant for more than five consecutive months. The same coverage is available if you are an individual homeowner or a small business limited liability company (LLC).

There are two options for the landlord policy: named peril or comprehensive coverage. Both have a wide range of endorsements to make the policy entirely flexible for your specific needs.

Customer service is available when you need it, with 24/7 claims support. The provider’s complaints are also lower than the national average for homeowners’ claims.

Conveniently, Foremost has flexibility with claims settlement. The landlord policy can be structured as an agreed loss value for your home if it is a total loss, or an actual cash value if your claim is for a partial loss.

Also, Foremost has multiple discounts available. For example, if you screen your tenants, then you may be eligible for a discount.

Obie: Best for Short-term Rental Insurance

In a few minutes (at most), I received one quote with three tiers of coverage:

  1. Basic costs $898 annually and included building coverage, $5,000 in business personal property, $18,000 in loss of rent with $500,000 per occurrence, and $1 million total in general liability coverage. It also had 3% inflation guard coverage.
  2. Complete costs $1,114 annually and had the same coverages as the Basic option—except the general liability limit increased to $1 million per occurrence and $2 million aggregate and the inflation guard rate increased to 6%. It also had some additional coverages, like $25,000 in water backup.
  3. Premium is Obie’s top-tier coverage and costs $1,200 annually. It had the same coverages as above but with increased limits, like $10,000 for business personal property and $50,000 for water backup. It also included 9% for inflation guard.

Each tier is customizable, giving you total control over the level of coverage you purchase for the property. After customizing the option to fit you best, you can then purchase the policy online.

Obie is a newer rental insurance company. It was founded in 2017 but has expanded rapidly and has over $4 billion in property insured in all 50 states. Its customers seem to be happy with the service they have received. Nearly 500 reviews have been posted online for Obie, which has an average rating of 4.9 out of 5 on Google.[1]

You can easily manage your Obie policy through your online account. If you have questions about the policy or billing or need to file a claim, you can email or call. Obie is only available during the weekdays.

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CBIZ: Best for Homes With Amenities

To obtain a quote, you will need to fill out an online application, and then an agent will contact you.

CBIZ’s vacation rental insurance policy can replace your dwelling or landlord policy and serve as one policy for the property. Its policy offers a mixture of dwelling coverage with a commercial general liability policy with a $2 million aggregate limit.

The policy also has a loss of income built into its standard coverage. You can even add bed bug cleanup as an endorsement with no deductible.

The type of property you insure with CBIZ is not an issue as the company has a broad appetite for different structures. Townhomes, single-family residences, condos, and duplexes are all covered

For convenience, CBIZ’s website offers a quick and easy system for quoting your vacation rental insurance. Answer a few specific questions and get a quote immediately.

You can contact the provider directly if an issue arises. Helpfully, CBIZ lists the contact information for all of the carriers it works with on the contact section of its website.

American Family: Best for Renting Out Your Home

Quotes are available only through American Family agents.

In the FAQ section of its website, the provider states the cost of insurance can range from $2,000 to $3,000 annually. It also provides discounts for certain upgrades you make, such as installing a smart home security system.

Two policies are available for your vacation rental needs:

  1. Second home insurance: This coverage is ideal for a home you use as an occasional family getaway.
  2. Short-term rental insurance: This policy is an endorsement to a standard homeowner’s policy that allows you to rent your home for up to 62 days a year. American Family has no problem with frequently renting the house out through Vrbo, Airbnb, or similar businesses—though any period beyond 62 days is not covered. This policy is excellent for snowbirds who leave their home for up to two months a year. Additionally, many retirees are on a fixed income, making the diminishing deductible a nice incentive to check out the provider.

The provider offers a 24/7 claims reporting line, or you can file a claim online. Online, you can also manage your policy and pay your premium.

American Family has multiple ways to save on insurance too. These include bundling an auto policy and generational discounts.

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Safely: Best for Guest Screening & Property Management

To get a quote, provide your information and a representative will reach out to you.

Safely’s policy provides coverage in three different areas:

  • Dwelling: up to $1 million
  • Contents: up to $10,000
  • Bodily injury: $1 million

There is no lost income or endorsements. Safely also has a broad range of coverage for structures.

Get an instant quote and purchase your policy through Safely’s website without having to talk to an agent. You also can submit a claim and manage your policy through its online portal.

The company has a streamlined claims process. Not only can you file a claim online, but the turnaround time from reporting a claim to receiving payment is under four days.

Frequently Asked Questions (FAQs)

Anyone who rents their home out for others to use needs vacation rental insurance. Vacation rental insurance protects your property and assets from liability, while also helping with lost rental income expenses. It covers gaps of coverage that your homeowners insurance will not.

The difference between the two coverages is the amount of time the property is rented. Some carriers require rental for a certain period of time or will place a limit on how often a home is rented out.

Expect to pay between $1,700 to nearly $3,000 annually for vacation rental insurance. Policies can cost more or less depending on the size, location, and amenities of the home. Vacation rental insurance usually costs 10% to 20% more than a homeowners policy.

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Bottom Line

If you rent out your home or have a second one you rent out regularly, you will want to ensure you have vacation rental insurance. I understand how important it is that your home and its memories are protected, which is why I have evaluated the best short-term rental insurance companies for you. Foremost Insurance is our overall best vacation rental insurance company.


Visit Foremost for a quote



Consumer review sources:
[1]Obie | Google Reviews

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