Vacation Home Property Management Services


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. 


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]

Michaela is our office manager.  She has lived in Cundy's Harbor her entire life.  She is incredibly knowledgeable about the area and uses that to assist tenants with their vacation choices.  Michaela handles all tenant correspondence. She is currently going to school for Accounting at University of Southern Maine.
Email: [email protected]

Josh is Heather's husband.  He helps to make our busy turn over days smoother by assisting us in the office and with maintenance issues that may arise.  

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

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.