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Vacation Rentals in Bailey Island, ME

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    All 36 Rentals in Bailey Island
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    From
    $271
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    1 / 33
    5 of 5 stars (5) Excellent
    4 Bedrooms / 2 Bathrooms / Sleeps 7
    Overview Reviews (5) Make Inquiry
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    $650
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    1 / 10
    5 of 5 stars (4) Excellent
    4 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Reviews (4) Make Inquiry
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    $114
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    1 / 4
    5 of 5 stars (1) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Reviews (1) Make Inquiry
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    $300
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    1 / 19
    4.5 of 5 stars (2) Very good
    4 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (2) Make Inquiry
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Spindrift has been featured in 'Coastal Living' magazine for a very good reason -- it is the ultimate Maine coastal cottage experience. Located on Bailey Island and perched above the surf as it rolls from open ocean into Little Harbor, it retains the coastal cottage vernacular despite having been... View all property information
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    5 of 5 stars Reviewed October 2, 2012
    My husband and I just got back from spending a week in this cottage. I can not say enough about it. The location is more than great. You awaken to the sound of the waves coming...
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    $250
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    1 / 19
    5 of 5 stars (4) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (4) Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Home Port has undergone a foundation-up renovation completed in August 2011. The house modernization design allows you to enjoy the magnificent view of Mackerel Cove and Mackerel Cove beach. Settled among houses that have come down through generations of lobster-men, this home enjoys a desirable... View all property information
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    $100
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    1 / 1
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    About this property
    This sweet single story cottage sits on Tip-Top Hillside, with views into Mackerel Cove and beyond. This property offers 2 bedrooms, 1 bathroom and a lovely kitchen, open to the living and dining area. The cottage is situated on a sunny lot, with a yard, complete with a lovely deck and sunset... View all property information
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    $225
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    1 / 9
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    Amenities & Details
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Bailey Island waterfront, bold surf, private, updated and location, location, location! This cozy, oceanfront cottage on Bailey Island oversees what was once called 'the most spectacular view in North America'. The ocean surrounds you and provides views from every window. The cottage itself... View all property information
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    From
    $213
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    1 / 8
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Magnificent renovated 19th Century Stone and Shingle Cottage overlooking Casco Bay retains historical atmosphere while having modern amenities. The home is located at the dead end of a road and which is surrounded by lush grass, trees and ocean. Past tenants state that 'their stresses left them for... View all property information
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    From
    $132
    / Night
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    1 / 1
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This pleasant year 'round cape is centrally located with a limited view of the Bay. Easy walk to water. There is a nice patio and yard. Cozy Fireplace to read by, or watch the beautiful sunsets! View all property information
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    From
    $85
    / Night
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    1 / 1
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This unique, and cozy Log Cabin is located on beautiful Mackerel Cove. The cabin is perfect for snuggling up by the fire. The view is very limited as the cabin is surrounded by trees. A sloping path through the woods leads to a lovely picnic area right on the water perfect for relaxing while taking... View all property information
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    From
    $121
    / Night
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    1 / 8
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    This cozy cottage is located on a small, quiet street, and captures ocean views. Take in the ocean breezes while enjoying a sunny Maine afternoon on the deck, and enjoy outdoor activities from the large, grassy yard. You are just a moment's walk to a rocky shorefront and small rocky beach! Please... View all property information
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    From
    $525
    / Night
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    1 / 35
    5 Bedrooms / 4 Bathrooms / Sleeps 11
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Summer Salt is an excellent waterfront property located on Bailey Island. The property offers magnificent open ocean views of Casco Bay and views of Ragged Island. Standing outside on the large back yard, one can hear the sound of the waves crashing on the pebbly shoreline. The sounds and views of... View all property information
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    From
    $110
    / Night
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    1 / 8
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Originally a turn-of-the-century guesthouse called Bonnyview, this charming cottage retains it's historic character and is furnished with period antiques. It has views of Mackerel Cove, a wrap-around porch with a screened-in dining area, and a peaceful, woodland setting. A public use path to Little... View all property information
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    From
    $100
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    1 / 6
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This Cottage sits one lot back from the Ocean creating a serene location with beautiful Ocean views. There is a path close by leading to the Giant Staircase. There are three bedrooms inside and one bathroom with a fireplace for the cold Fall nights. Enjoy the views from the glassed in sun porch. View all property information
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    From
    $171
    / Night
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    1 / 1
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Picture your first day on your Bailey Island vacation....... Sleep in and rise to the sound of sea gulls catching their breakfast as lobster boats head out of Mackerel Cove. Take your coffee and newspaper out to your adirondack chair perched above your own pebble or sand beach 20 steps below.... View all property information
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    From
    $85
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    1 / 5
    Studio / 1 Bathroom / Sleeps 2
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    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This studio garage apartment is located on Harpswell Sound, offering beautiful sunset views and steps to the rocky shore. There is a queen futon in the living area. View all property information
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    From
    $128
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    1 / 1
    2 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This lovely home is situated on a sunny open lot, with a lush green lawn that rolls to the shore of Mingo Cove. Enjoy 100' of tidal water frontage, great to swim, kayak or collect treasures. You will fall in love with the spectacular sunrise views looking over neighboring islands and out to the... View all property information
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    From
    $135
    / Night
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    1 / 1
    3 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    This 3 bedroom cottage is located on a half acre lot on the west side of Bailey Island. The 1846 cottage is updated with all of the modern amenities. Enjoy a meal at the picnic table or dine in with water views. View all property information
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    From
    $192
    / Night
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    1 / 1
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    This lovely cottage is situated on a dead end road, perched above Little Harbor. Enjoy spectacular Easterly views, and listen to the waves crashing upon the ledges from nearly every room. There is a great wrap around porch to enjoy all the beauty the outside has to offer. Be sure to bring your... View all property information
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    From
    $100
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    1 / 1
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    A very new and charming cozy cottage. Centrally located on the Island at the end of Steamboat road. Shared pebbly beach frontage just steps away from the deck, beautiful south westerly sunset views. There are chairs provided to sit on the beach and soak up the sun and salt air. Watch the lobster... View all property information
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    From
    $127
    / Night
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    1 / 1
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Please be aware that the stairs up to the bedroom are like a staircase on a boat - they are quite steep - see pictures. Picture your first day on your Bailey Island vacation....... Sleep in and rise to the sound of sea gulls catching their breakfast as lobster boats head out of Mackerel Cove. Take... View all property information
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    From
    $157
    / Night
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    1 / 1
    Studio / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Picture your first day on your Bailey Island vacation....... Sleep in and rise to the sound of sea gulls catching their breakfast as lobster boats head out of Mackerel Cove. Take your coffee and newspaper out to your Adirondack chair perched above your own pebble or sand beach 20 steps below.... View all property information
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    From
    $314
    / Night
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    1 / 1
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    This newly constructed home offers spacious and sun filled living spaces,complete with all the comforts of home while basking in the beauty of all Bailey Island has to offer. Enjoy entertaining from the large, open kitchen/living/dining area, or relaxing on the waterside screened porch or multiple... View all property information
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    From
    $85
    / Night
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    1 / 1
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This charming Cottage is located in a great neighborhood by Lowells Cove. The Cottage has a nice yard, and an outside patio, with gas grill, and lounge chairs, and a view of the water. There is a path from the house to Lowell's Cove for swimming and water access. The rocky swimming area has long... View all property information
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    From
    $160
    / Night
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    1 / 1
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The Sea Salt Cottage is a charming and comfortable 1905 Vintage Seasonal cottage located on quiet, peaceful, picturesque Bailey Island, Maine. Facing due East, you can enjoy the sunrise, watch the lobster boats, or enjoy the sound of the crashing surf while relaxing on the covered front porch. The... View all property information
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    From
    $107
    / Night
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    1 / 1
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This lovely New England style cottage is situated on a dead end road in a great Bailey Island neighborhood! This house does not have water views, but what it lacks in views it makes up for with its great location for exploring the island on foot, such as the Giant Stairs walking path where you can... View all property information
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    From
    $328
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    1 / 9
    4 Bedrooms / 2 Bathrooms / Sleeps 7
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    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    This year round oceanfront home sits right above the ledges on the Eastern shore of Bailey Island. The expansive open ocean views expand to Small Point and beyond. This home offers 4 bedrooms, 2 bathrooms, a large living and dining area with walls of windows, washer/dryer, and a newly remodeled... View all property information
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    From
    $214
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    1 / 6
    5 Bedrooms / 1 Bathroom / Sleeps 6
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    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This turn of the century cottage tucked along the rocky shore, is a true Maine cottage experience. Listen to the waves crash onto the ledges of Little Harbor, as you sip your coffee and enjoy the easterly views from the charming waterview porch. While this cottage keeps its charm of yesteryear it... View all property information
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    $103
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    1 / 6
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The simplicity of this quaint, coastal, 2 bedroom cottage is what affords it such charm! This vacation cottage brings you gorgeous sunset views out to the ocean from both front and rear decks. Located on a quiet road with steps leading directly to a rocky shore front, you are within walking... View all property information
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    From
    $78
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    1 / 5
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Enjoy the Central location of this cottage, and its beautiful Easterly views of the Ocean. Only a short walk to the beach. The right of way is to a small rocky area and stone beach. Cedar beach is also within walking distance. The Deck has a roll out canopy for shade. Please note: When looking up... View all property information
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    $235
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    1 / 8
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    • ?
    About this property
    Four bedroom, 3 bathroom fishermans cottage on beautiful Mackerel Cove. View all property information
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    $171
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    1 / 8
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    This 3 bedroom waterfront cottage is located in a quite neighborhood right on the water. Enjoy a private fenced in back yard with a nice patio complete with fire pit and plenty of seating to relax and take in the salty air. There are stone steps down to the water's edge to search the rocks at low... View all property information
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    $121
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    1 / 5
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This spacious and sunny garage apartment is located at the edge of crashing surf in Little Harbor. Beautiful and Bold southeast views. Enjoy sunrises or watching the working fishing boats as you listen to the crashing surf. This rental is not appropriate for young children. **Please note - this... View all property information
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    From
    $128
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The Gagnier's cottage is an adorable ranch which sits on top of a hill, and provides spectacular sunset views from the wrap around deck, or inside on the main level. There is a right of way to the rocky oceanfront directly across the street. The daylight basement does have a full bathroom, and a... View all property information
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    From
    $250
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    1 / 8
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    This 3 bedroom, 2 bathroom, year round home has a large deck and steps to the rocky shore! From the deck watch the lobster boats get their daily catch and enjoy spectacular sunset views over the Harpswell Sound. There is a one car garage with the rental. Other parking is limited. The studio... View all property information
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    $185
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    1 / 6
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Look no further! This recently renovated cape is perched high on the island offering panoramic, open ocean views, complete with breathtaking sunrises & sunsets. Enjoy the gorgeous kitchen and charming dining room and living area, as well as the large lawn to enjoy the view and sweet salt air. This... View all property information
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