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Southport Vacation Rentals

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    Don't let other travelers get your favorite Southport vacation rental. You're so close to securing your perfect getaway. Book today.
    All 16 Rentals in Southport
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Enjoy this little cottage in the woods built by Grandy and Grandma!1 / 20
    (6)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Southport, Mid Coast Maine 04576
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Classic Maine Ocean Front Cottage.  Sunrise over Ocean and Islands.1 / 23
    (4)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Southport, Mid Coast Maine 04576
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Historic House Featured in March 2015 House Beautiful Magazine!1 / 23
    (4)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    Southport, Mid Coast Maine 04576
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    6 bedroom home on Deckers Cove in Southport near Boothbay Harbor with Kayaks .1 / 21
    (7)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Southport, Mid Coast Maine 04576
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    Charming Plumpoint Cottage On Southport Island1 / 11
    (8)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Southport, Mid Coast Maine 04576
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Southport, Mid Coast Maine 04576
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Stone House on Bayberry Lane with Magnificent Views1 / 19
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Southport, Mid Coast Maine 04576
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 14
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    THREE SEAS | MCKOWN POINT | JUNIPER POINT ASSOCIATION | ASSOCIATION BEACH, DOCK1 / 10
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed September 28, 2014
    We love comming to this cottage. It is one of the most relaxing places on earth. It has all the conviences of home with none of the stress. Close enought to loads of...
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    About this property
    THREE SEAS Perfectly located on McKown’s Point and part of the Juniper Point Association this beautifully quaint little two bedroom cottage is the perfect family retreat for your summer vacation! Enjoy views of Mouse and Squirrel Island from the living room windows and grassy yard. Open the windows...
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    Southport, Mid Coast Maine 04576
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Enjoy Island Living with your family or friends in this water view, 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 cottage. Comfortably furnished with an eye to family...
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    Southport, Mid Coast Maine 04576
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    MOLLY’S CAPEis 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 plenty...
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    Location Information
    Southport, Mid Coast Maine 04576
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
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    Pet friendly
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    About this property
    PIFFI BIFF Piffi Biff is 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 shore birds, sailboats, yachts and lobster...
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    Southport, Mid Coast Maine 04576
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Come spend your vacation at the edge of the sea. Ledgemere Cottage provides you with spectacular 180 degree views of the Atlantic Ocean, Fisherman's Island, Ram Island, Squirrel Island, Entrance to Boothbay Harbor, and Cuckolds Lighthouse - not to mention the boats you will enjoy watching. Walk...
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    Southport, Mid Coast Maine 04576
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    BARNACLES COTTAGE is a classic Maine summer cottage and is the perfect setting for a memorable holiday. Rocky coastline, open ocean, and small private beach are just a few of the natural wonders at Barnacles. The cottage features hand-hewn beams and wide boards, original to the structure circa...
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    Location Information
    Southport, Mid Coast Maine 04576
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Southport Flight and Weather Info
    Airports nearby (1)
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    Portland Intl Jetport
    34.0 miles from Southport
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