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Our Team

Our Team

Your Island Connection is a family-run business that has been managing private waterfront rental homes and cottages in the Harpswell Islands area of Midcoast Maine since 1982. Throughout the years our business has grown from only a few cottages to the more than sixty homes and cottages that you see listed with us today. Here at Your Island Connection, we feel that by building personal connections with owners and tenants we are able to provide you with the satisfaction that will create comfort and memories for years to come. Our staff consists of friendly, hardworking, natives of the area who are proud of the fishing community they reside in and want to share its hidden treasures with you. Please know that 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 of Your Island Connection. In 2011 Heather and her husband purchased this local business and have enjoyed every minute of interacting and making longtime friends with the travelers on the island. Heather spends a lot of time out at houses making sure they are ready for travelers. While running a business and having three daughters under nine keeps her busy, in her off-time she enjoys running, volunteering at Harpswell Community School and helping with her children’s activities. Heather also serves as the President of the organization Vacation Rental Professionals of Maine (VRPOMe) as she is continually working to improve clients’ vacations and Home Owner’s rental experiences.
Email: hallen@mainerentals.com

Samantha has grown up here in Maine, and she feels blessed to be able to live and work on the beautiful coast. Recently, she and her boyfriend bought their first home in Bath, where they care for three cute rescue pets; Raz, their dog, and two cats; Hemmie and KB. Samantha enjoys spending time outside, especially in her sneakers. She completed her first international marathon a few years ago in Niagra Falls. You can also find her skiing on one of the slopes in Maine, discovering treasures from antique shops, and playing the piano. Samantha comes to Your Island Connection with over eight years of experience in the world of finance. Several of these years were spent working on the Florida coast. As the new Office Manager, she is looking forward to helping our guests plan their seaside vacations, as well as ensuring a stress-free experience for both our property owners and valued guests.

Cara Cara was raised in Kennebunk, and her heart is firmly rooted in Maine. She graduated from Temple University in Philadelphia, where she was on the fencing team and received her BFA in glass and ceramics. Through fencing, she has traveled around the world, from Cuba to Finland, Croatia to Italy and beyond, and maintains that Maine is the best place to call home. As a realtor, Cara loves the crossover experience between real estate and working with Your Island Connection. Currently, she and her partner live in Bowdoinham with their daughter Luna. They have slowly been renovating an antique barn into a studio, complete with woodworking and glassblowing equipment. On the weekends, Cara can usually be found with her family somewhere on a boat or otherwise near the water.

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.

Others: Throughout the summer, you will find that we have many additional helpers assisting us to ensure that your vacation runs smoothly. Your Island Connection contracts with many independent contractors to ensure your cottages get cleaned and maintenance issues are taken care of.

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