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Holiday Homes in Southport

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    Travellers to Southport are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    All 16 Rentals in Southport
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
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    • Ocean Views
    • Waterfront
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    • DVD Player
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THIS PROPERTY RENTS SATURDAYS-SATURDAYS JUNE - SEPTEMBER. 7-NIGHT MINIMUM REQUIRED. Off-Season Arrival and Departure dates may be flexible. A treasured Maine cottage at the edge of the Atlantic Ocean on Southport Island is waiting for you to settle in for a memorable Maine vacation. Here,...
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    Newagen, Southport 04576
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THIS PROPERTY RENTS SATURDAYS-SATURDAYS JUNE - SEPTEMBER. 7-NIGHT MINIMUM REQUIRED. Off-Season Arrival & Departure dates may be flexible. ___________________________________________ Come spend your vacation at the edge of the sea. Ledgemere Cottage provides you with spectacular 180...
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    Southport, Mid Coast Maine 04576
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Three Bedroom Cottage on Southport Island Overlooking Decker Cove. Enjoy Island Living with your family or friends in this three bedroom, two bath cottage overlooking Decker Cove. Walk to nearby Robinson's Wharf for lunch or dinner or to buy fresh lobster from our local lobstermen to cook at your...
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    Southport, Mid Coast Maine 04576
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    A classic log cabin nestled among the pines is ready for you to settle in for a memorable Maine Vacation. This three bedroom, two bath cottage on Southport Island is well equipped and comfortably furnished throughout. Enjoy the rustic feel with contemporary furnishings inside and the breathtaking...
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    Newagen, Southport 04576
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    6 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Grill
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    Pet friendly
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    About this property
    The beautifully renovated 1927 Ocean's Edge Cottage affords 270-degree ocean views on Pratt's Island. This 6BR estate offers Maine coastal living at its most spectacular, with expansive lawns, English gardens, dock, oceanfront bedrooms, full kitchen, and proximity to all Boothbay Harbor activities....
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    Southport, Mid Coast Maine 04576
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 14
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Smoking allowed
    About this property
    THIS PROPERTY RENTS BY THE WEEK OR MONTH, JUNE - SEPTEMBER. Off-Season Arrival and Departure dates may be flexible. Please ask your reservationist for more details regarding long-term stays. Come to experience Maine, the way life should be, at Ocean Way. Here you can breathe in the fresh ocean air...
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    Southport, Mid Coast Maine 04576
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MOLLY’S CAPE is the perfect place for an active family or those wanting to soak up some sun on the beach. Located on the west side of Southport Island, Molly’s Cape provides the perfect out-of-the-way location with easy access to Boothbay Harbor. An open-air deck and plush green lawns provide...
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    Southport, Mid Coast Maine 04576
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Catch sunrises over the water and spectacular views of Squirrel Island and Spruce Point from your 5BR/4.5BA Southport Island retreat. Bring the whole family for an epic seaside getaway -- there’s plenty of space for your group to stretch out in the formal living room, casual family room, and...
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    Southport, Mid Coast Maine 04576
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A treasured family home at the edge of the Atlantic Ocean is ready for you to settle in for a memorable Maine Vacation. This pet-friendly, two-bedroom, one and a half bath cottage is well equipped and comfortably furnished throughout. Savor the solitude and sounds of the ocean without being too far...
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    Southport, Mid Coast Maine 04576
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Tucked away on Southport Island is this little guest house for two. Located just across the swing bridge from Boothbay Harbor, Little Nick offers one bedroom, a bright and sunny living area, galley style kitchen, and a deck with peaks of the water. Robinson's Wharf is right around the corner where...
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    Southport, Mid Coast Maine 04576
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Balcony
    • Grill
    • Patio
    • Ocean Views
    • Waterfront
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cute-as-a-button newly renovated waterfront cottage is located on Southport Island across the swing bridge from Boothbay Harbor. 'Periwinkle' sparkles with fresh coastal decor and hardwood floors throughout. The first of two bedrooms offers the option of a king size bed which can be converted...
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    Southport, Mid Coast Maine 04576
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Waterfront
    • DVD Player
    • Ocean Views
    • Grill
    • Washer
    • Patio
    • Wi-Fi
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Piffi Biff, a beautiful cottage located on the historic Southport Island on the Boothbay peninsula. With incredible views of the Atlantic Ocean, Squirrel Island, Boothbay Harbor, Burnt Island, you will also see porpoises, whales, migratory shorebirds, sailboats, yachts and lobster boats!...
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    Southport, Mid Coast Maine 04576
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • DVD Player
    • Balcony
    • Wi-Fi
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    • Cable/satellite TV
    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled on pristine Southport Island, this charming 2BR/2BA cottage – affectionately known at Romley House – offers a welcoming respite with picturesque Maine scenery. Interior features include hardwood floors, a fireplace, post and beam ceilings, rustic furnishings, and vintage decor. Your getaway...
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    Location Information
    Southport, Mid Coast Maine 04576
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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