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Business Details
50+ Years
experience
Your Trusted Florida Keys Insurance Partner
Regan Insurance Agency has been family owned and operated in the Florida Keys since 1958, establishing itself as a trusted leader in the insurance industry. Our team of experienced professionals specializes in addressing the unique insurance risks faced by residents and businesses in this distinct coastal region. For over five decades, we have prioritized personalized service, offering comprehensive, competitive, and customized coverage solutions tailored to clients' specific needs. Our commitment extends beyond initial sales, ensuring ongoing local support and expert guidance through life's various challenges. As a multi-generational agency, we blend deep-rooted community knowledge with modern insurance expertise to protect all aspects of the Florida Keys lifestyle. From home and auto insurance to specialized coverage for boats and jewelry, our approach remains consistent: assess individual exposures, explain policy options clearly, and empower clients to make informed decisions.

The 2019 rebranding to Regan Insurance Agency reflects both our storied legacy and forward-looking vision, with fourth-generation members continuing this tradition of excellence. Our focus on community, combined with a team of seasoned professionals and recent recruits, ensures we deliver quality products, specialized knowledge, and dependable service. We actively engage with local insurance developments, providing timely insights and customized solutions that address evolving risks. This enduring commitment to personalized service, regional expertise, and generational continuity defines our approach to protecting Florida Keys residents and businesses.
Services
Home Insurance Auto Insurance Boat Insurance Jewelry Insurance Business Insurance
Details
  • Year established: 1958
Highlights and features
  • We offer 65 years of Florida Keys insurance expertise since 1958
  • Our team provides personalized, local attention even after the sale
  • Fourth-generation family members continue our tradition of excellence
  • We specialize in addressing unique coastal insurance risks of the Keys
  • Our agents clearly explain policy options to enable informed decisions
Services
Home Insurance
Protect your Florida Keys residence with customized home insurance policies addressing coastal risks like hurricanes and flooding. Our specialists analyze your property's unique exposures to create comprehensive protection plans that cover structural damage, personal belongings, and liability concerns. With deep understanding of local building codes and climate challenges, we help homeowners secure tailored coverage that balances protection and affordability.
Auto Insurance
Get customized auto insurance solutions for Florida Keys drivers that address regional driving conditions and risks. We offer policies covering collision damage, comprehensive protection against weather-related incidents, and liability coverage tailored to individual needs. Our agents help clients navigate Florida's insurance requirements while finding cost-effective options that protect vehicles and financial security in case of accidents or unexpected events.
Boat Insurance
Specialized boat insurance policies designed for Florida Keys watercraft owners address unique marine risks. Our coverage options protect against damage from storms, accidents, and theft while covering liability for water-based activities. With knowledge of local boating regulations and environmental factors, we create tailored protection plans for everything from small fishing boats to luxury yachts operating in the Keys' coastal waters.
Jewelry Insurance
Custom jewelry insurance solutions protect valuable items against loss, damage, and theft for Florida Keys residents. We offer specialized coverage beyond standard policy riders, including protection for accidental damage, mysterious disappearance, and increasing value clauses for appreciating assets. Our agents work closely with clients to document valuables and create policies that maintain jewelry's sentimental and financial worth.
Business Insurance
Comprehensive business insurance packages tailored to Florida Keys commercial operations address industry-specific risks. We provide protection for property damage, liability claims, business interruption, and specialized exposures unique to coastal enterprises. Our agents work closely with local business owners to create customized packages combining general liability, commercial property coverage, and industry-specific endorsements that address hurricane preparedness and other regional concerns.
People
Carlton Regan
Founder
Established the agency in 1954, laying the foundation for multi-generational family leadership and Florida Keys insurance expertise.
Robert E. Regan
Co-Owner
Joined his father in 1972, expanding operations and building the agency's reputation for personalized coastal insurance solutions.
Sara M. Roth
Risk Management Specialist
Fourth-generation member with advanced degrees in risk management insurance from Florida State University, providing modern expertise since 2023.
Joe H. Roth III
Managing Owner
Led rebranding efforts in 2019, combining family legacy with forward-looking vision while maintaining industry certifications.
Jennifer Miller Roth
Operations Manager
Licensed professional with 2020 credentials who oversees daily operations, ensuring smooth delivery of insurance services.
Questions
What insurance services do you offer for Florida Keys residents?
We provide customized home, auto, boat, jewelry, and business insurance solutions tailored to the unique coastal risks of Florida Keys residents and businesses.
How can I get a personalized insurance quote?
Contact us through our website or call (305) 852-3234 to schedule a consultation where our agents will assess your needs and propose tailored coverage options.
Do you specialize in Florida Keys-specific insurance risks?
Yes, our agency focuses specifically on the unique insurance challenges faced by Florida Keys residents, including hurricane preparedness and coastal property protection.
How does your claims process work?
We provide personalized support throughout the claims process, guiding policyholders through documentation requirements and coordinating with carriers to ensure timely resolution of Florida Keys-specific claims.
Can you help businesses with Florida Keys commercial insurance needs?
Our agents create comprehensive commercial insurance packages addressing property damage, liability, business interruption, and specialized coastal risks for Keys businesses.
Reviews (4)
Jennifer Miller
Apr 19, 2022 Report
Knowledgeable and friendly staff! They really took the time to explain everything to me. You don't find agencies that care about their clients like this anymore! Would recommend 100 times!
Tim Marcus
Feb 28, 2022 Report
I can't say enough about how great you all are. Holly was amazing in helping me get several policies set up for our property. I leaned on her knowledge and expertise, and she made everything incredibly easy even when I was in a pinch on timelines. She went above and beyond to get it done, and was incredibly nice. More companies need to do business this way!
David Yglesias
Jan 12, 2018 Report
Joe Roth and the entire Regan Insurance team are very professional, efficient and affordable. I always feel they have my best interest at heart when helping me select insurance. This personalized service is very difficult to find in this age of online sales. Thank you Joe!
Tony Germin
Jun 17, 2017 Report
Everyone at Regan Insurance are veryhelpfull and professional. I can say that it's a pleasure to deal with this office.