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About Us

THE BUSINESS

Your Island Connection is a family business that has been managing private oceanfront rental homes & cottages in the Harpswell Islands area of Midcoast Maine since 1982. Throughout those years we have grown from only a few cottages to the more than 60 homes & cottages that you see listed today. Building personal connections with owners and tenants is something we feel is an essential part of our business. At Your Island Connection, you will find friendly, hardworking natives of the area who are proud of our fishing community and want to share its hidden treasures with you. We are willing to meet with you in person, discuss options over the phone or converse via email to help you find a property that will fit your needs.

THE PEOPLE

Heather is the owner. She lives in Cundy's Harbor with her husband, a reputable lobsterman on Bailey Island, and their three daughters. A former teacher, Heather has achieved her Master's Degree in Educational Technology, and since found her interest in the marketing and management of Your Island Connection. Her native background offers visitors a wealth of knowledge in regard to area attractions, while her technological background ensures that clients' vacations will be spent worry-free in regard to their accommodations. Email: [email protected]

Vacation Home Property Management Services

We are proud members of Southern Midcoast Maine Chamber of Commerce, Vacation Rental Management Association (VRMA), Maine Tourism Association, Vacation Rental Professionals of Maine, and The Harpswell Business Association. We would like to thank Steve Phillips Productions for creating the video for our business and some of our feature photographs.

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Meet The Team

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Heather

Heather is the owner. She lives in Cundy's Harbor with her husband, a reputable lobsterman on Bailey Island, and their three daughters. A former teacher, Heather has achieved her Master's Degree in Educational Technology, and since found her interest in the marketing and management of Your Island Connection. Her native background offers visitors a wealth of knowledge in regard to area attractions, while her technological background ensures that clients' vacations will be spent worry-free in regard to their accommodations. She is the previous President of Vacation Rental Professional of Maine and continues to stay up to date with her industry news and policies. Outside of work she enjoys running, reading and coaching youth sports.

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Josh

Jack of All Trades

Josh is our jack of all trades. Josh is Heather’s husband and a local lobsterman out of Mackerel Cove. Growing up on Bailey Island Josh understands several components of how houses are built and function allowing him to handle some maintenance issues that arise. You may see Josh in and out of our office often, as he helps with turnovers on Saturdays and care-taking during the winter months.

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Andrea

Vacation Rental Specialist

Andrea was born and raised in Maine. Married to a Phippsburg lobsterman, their blended family includes 6 children, 2 cats and a spoiled dog. Andrea started with us in September 2022 after more than 25 years in the hospitality industry. With a knack for organization and an eye for detail, she understands the importance of making sure both our guests and owners have a stress-free experience with us. When she is not planning the family's next Disney vacation, Andrea enjoys baking, beachcombing and Maine road trips.

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Madison

Vacation Rental Specialist

Madison is from “away.” She moved to Maine 18 years ago from the south (although originally from Wisconsin).  She was a paralegal for 25 years before retiring from the legal profession and joined our team in September 2021.  She competed for many years in 5K, 10K, and half marathons having once been ranked nationally.  She has an adorable Westie, Winston and a demanding cat, Isabella.  She works with various dog rescue organizations in the area doing home visits for potential adopters.

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Others

Throughout the summer you may find we have many additional helpers during our busy season to assist in your vacation running smoothly.

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