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Come to the Ocean
Come to Life From rustic cabins to luxurious, contemporary homes, Your Island Connection proudly represents over 60 vacation homes
to accommodate the perfect stay for you, your friends, and your family. Come to the ocean!

Come to the Ocean
Come to Life From rustic cabins to luxurious, contemporary homes, Your Island Connection proudly represents over 60 vacation homes
to accommodate the perfect stay for you, your friends, and your family. Come to the ocean!

Pet Friendly

VACATION RENTALS

Waterfront

VACATION RENTALS

Water View

VACATION RENTALS

Winter Rentals

VACATION RENTALS

Prime Properties

Your Island Connection proudly represents over 50 waterfront and water view homes to accommodate your stay. From rustic cabins to luxurious contemporary homes, we have the perfect spot on the water for you, your friends, and your family. Our rentals are weekly, monthly, and seasonal and our office is open year round for your convenience. Make your coastal vacation authentic and memorable by staying in one of our exclusive waterfront rental properties.

Personalized Service

We strive to give you the most professional and courteous service in town! Our communication and attention to detail are top-notch. We have created literature specific to each home. Your Island Connection is a locally owned and operated rental agency serving the Islands for over 35 years, including Bailey Island, Orr's Island, Great Island, Cundy's Harbor, and Harpswell. Our knowledgeable crew of friendly, hardworking area natives are here to assist you. We are proud of our fishing community and enjoy sharing its hidden treasures with our property owners and renters alike. Building personal connections with our clients is something we feel is an essential part of our business--we take great pride in providing excellent, timely service to both our owners and renters!

Local Expertise

All of us here at Your Island Connection are familiar with and love Harpswell - we have become quite the experts in the area. Whatever you are seeking for your time here, we can help you find and experience it. From where to get the best local seafood, and the best spots for entertainment, fishing, hiking, beaches, and more - our crew is here to help build your dream vacation.

Professionally Managed

Our collection of Harpswell area homes represent the ultimate experience of a traditional New England vacation. We are sure you will find the perfect vacation home. Well-appointed and maintained, our vacation rentals offer many comforts of home while still holding onto our small town charm. If you are looking for area information, we have a whole section on our website dedicated to just that. We are available 24/7!

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Find Your Place

The Harpswell Islands are a coastal Maine vacation destination. With 216 miles of coastline on Casco Bay, Harpswell is an unspoiled coastal community. Here you will enjoy scenic landscapes including pebbly beaches, rocky shorelines, and breathtaking sunrises & sunsets. Harpswell boasts an authenticity you will not find elsewhere in Maine, with some of the few remaining working lobster wharves and fishing villages. You can take pleasure in sea kayaking, hiking trails, beach lounging, maritime history, and indulging in the freshest local seafood! The Harpswell Islands are a perfect spot to escape from the stresses of daily life. Relax and renew by the ocean’s salty breezes or make day trips to other parts of Maine with Harpswell’s convenient location in the Mid-Coast area.

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Our 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.

Contact Us
Call Us Today!(207) 833-7779

Featured Properties

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A Point of View

  • 2 Beds
  • 2 Baths
  • 7 Guests
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Edgecliff

  • 1 Beds
  • 1 Baths
  • 3 Guests
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Blue Heron

  • 2 Beds
  • 1 Baths
  • 5 Guests

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Places To Eat

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Tours, Launches & Marinas

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Beaches/Hiking Trails

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All Activities

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Guest Testimonials

The service is professional, swift, and comprehensive. Always friendly; all members of the team go the second mile.

John & Kathleen |

Super helpful staff helped me choose the best house for our family vacation and were great to talk to leading up to the trip, as well as while we were there. Excellent communication. I was overwhelmed trying to choose the right house, but they talked through what I was looking for, and helped me find the perfect place! It was nice to have a person to talk to, and then the website to review details and see pics, etc.

Amy |

Wonderful folks to work with in every respect. They lack nothing in professionalism and attention to detail. Very communicative and helpful.

Brad |
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