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Find Landlord Insurance Agents Near You in Winter Haven, FL

Compare landlord insurance agents in Winter Haven. Review contact information and insurance categorys before you decide.

19 agents listed
Updated May 2026
Winter Haven, FL
Important: Listings are compiled from publicly available sources and have not been independently verified by BeforeInsuranceUSA.com. We do not endorse any agent or guarantee outcomes. Verify licensing and disciplinary status with the Department of Insurance of Florida before hiring.
Showing 19 landlord insurance agents in Winter Haven, FL Listings are displayed in no particular order and are not ranked by BeforeInsuranceUSA. Order does not constitute a recommendation or endorsement of any agent.
Rob Semans - State Farm Insurance Agent
639 1st St S, Winter Haven, FL 33880
(863) 299-1274 robsemans.com
Team Barfield - Barfield Insurance
141 5th St NW #302, Winter Haven, FL 33881
(863) 662-3134 teambarfield.com
Barfield Insurance & Financial Services Inc.
110 Spirit Lake Rd Unit 5, Winter Haven, FL 33880
(863) 293-5400 insurewithbarfield.com
Joseph Bullington: Allstate Insurance
1900 Havendale Blvd NW ste c, Winter Haven, FL 33881
(863) 299-6449 agents.allstate.com
Karen Bryan - State Farm Insurance Agent
391 Ave A SW, Winter Haven, FL 33880
(863) 268-2800 choosekaren.com
Rob Geraghty - State Farm Insurance Agent
6996 Cypress Gardens Blvd, Winter Haven, FL 33884
(863) 877-0672 insurerob.com
Ryan Gunkel - GEICO Insurance Agent
5935 Cypress Gardens Blvd Suite 200, Winter Haven, FL 33884
(863) 269-4700 geico.com
GreatFlorida Insurance: Brock Schnabel
5658 Cypress Gardens Blvd, Winter Haven, FL 33884
(863) 594-2600 winterhaven.greatflorida.com
Dan Mann - State Farm Insurance Agent
6380 Cypress Gardens Blvd, Winter Haven, FL 33884
(863) 318-8881 danmanninsurance.com
American Insurance Inc
3610 Havendale Blvd, Winter Haven, FL 33881
(863) 965-2886 americaninsuranceinc.com
Garland Insurance fka Victory Insurance
116 W Central Ave, Winter Haven, FL 33880
(863) 683-9334
Clearvue Insurance Agency (Formerly Lorna Wilson Agency)
308 Ave G SW Suite 201, Winter Haven, FL 33880
(863) 866-8990 clearvueinsurance.com
Cypress Insurance Management
3021 Cypress Gardens Rd, Winter Haven, FL 33884
(863) 326-1885 cypressinsuranceonline.com
L.B. Yates - State Farm Insurance Agent
5405 Cypress Gardens Blvd, Winter Haven, FL 33884
(863) 324-2411 lbyates.com
Sealy Insurance
3395 Cypress Gardens Rd, Winter Haven, FL 33884
(863) 324-3100
Dershimer Insurance Agency
190 Avenue A NW, Winter Haven, FL 33881
(863) 299-8330 dershimerinsurance.com
Carroll-Marshall Insurance, Inc.
205 Ave G SW, Winter Haven, FL 33880
(863) 293-1111 cminsure.com
Ewing Blackwelder & Duce Insurance
1330 Havendale Blvd NW, Winter Haven, FL 33881
(863) 293-2838 ebdins.com
Brightway Insurance, The Bailey and Associates Agency
150 3rd St SW Suite 203, Winter Haven, FL 33880
(863) 614-1300 brightwaybaileyandassociates.com

A landlord insurance agent in Winter Haven Florida helps rental property owners protect their investments. Florida law requires landlords to maintain certain coverages for liability and property damage. Local agents understand the unique risks of Central Florida including hurricane exposure and seasonal tenant patterns.

What Does a Landlord Insurance Agent in Winter Haven Cost?

Landlord insurance in Winter Haven Florida typically costs between 1200 and 4000 dollars per year for a single-family rental property. Premiums depend on the dwelling value coverage limits deductible and property location within flood or wind zones. Older homes or properties with wood roofs may have higher rates. This is general information and not insurance advice.

* Cost estimates are general ranges based on publicly available data and compiled using automated research tools. Actual fees vary by agent and case complexity. This is not insurance advice — consult directly with an agent for fee specifics.

Frequently Asked Questions

What does landlord insurance cover in Winter Haven Florida?
Landlord insurance typically covers the dwelling structure liability protection and loss of rental income. In Florida policies often include windstorm and flood exclusions so separate coverage may be needed. A local agent can explain which perils are standard and which require endorsements.
Is landlord insurance required by law in Florida?
Florida law does not mandate landlord insurance but most mortgage lenders require it for rental properties. Without coverage you risk financial loss from tenant damage liability claims or natural disasters. A Winter Haven agent can help you meet lender requirements and state-specific obligations.
How do Florida landlord insurance costs compare to other states?
Florida landlord insurance premiums are higher than the national average due to hurricane and sinkhole risks. Winter Haven rates also reflect local claims history and property age. An agent can provide quotes tailored to your specific rental property location and coverage needs.