1 Bedroom

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2 Bedrooms

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3 Bedrooms

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4 Bedrooms

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Why Choose Your Island Connection?

Professionally Managed

Our collection of Harpswell area homes represents the ultimate experience of a traditional New England Vacation, you are sure to 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. Breathe in the fresh, salt air, as you relax and take in all the sights and sounds of the sea.

Local Expertise

The entire crew at Your Island Connection lives in and loves Harpswell - and we've become quite the experts in the area. Whatever you are seeking from your time here, someone on our crew is sure to have experienced it and will be ready to give you helpful hints along the way. 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.

World Class Service

We strive to give you the most professional and courteous service in town! Our communication and attention to detail is top notch. We have created literature specific to each home, to ensure you will have answers to any questions at your fingertips. If you are looking for area information, we have a whole section on our website dedicated to just that. We are available 24/7!


A Perfect Oceanfront Vacation Awaits You!

Welcome to beautiful Mid Coast Maine! Make your coastal vacation authentic and memorable by staying in one of our exclusive waterfront rental properties. Your Island Connection proudly represents over 60 waterfront and water view homes to accommodate your stay. From rustic cabins to luxury, contemporary homes; we have the perfect spot on the water for you, your friends and your family to vacation.

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 won’t find elsewhere in Maine with some of the few remaining working lobster wharfs and fishing villages, you will also take pleasure in sea kayaking, local seafood, hiking trails, maritime history, and so much more! 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 of Maine.

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, have over 50 years of combined service in the hospitality industry. We are proud of our fishing community and enjoy sharing its hidden treasures with our owners and renters alike. Building personal connections with owners and tenants is something we feel is an essential part of our business. We take great pride in providing excellent, and timely service to both our owners and renters. We offer weekly, monthly, and seasonal oceanfront vacation rentals. Our office is open year-round for your convenience. Let us help you find the perfect place to make the most of your vacation on the coast of Maine.