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262 Houses

    13

    Doc`s_Place_Southport

    Mid Coast Maine / Southport

    Southport house

    3 6 min stay varies

    • 3 bedrooms
    • sleeps 6
    • min stay varies
    • Child Friendly
    • Pet Friendly

    Price per night from

    $293

    Price per night from

    $293

      26

      Ledgemere_Cottage_Southport

      Mid Coast Maine / Southport

      Southport house

      3 6 min stay varies

      • 3 bedrooms
      • sleeps 6
      • min stay varies
      • Child Friendly
      • Pet Friendly

      Price per night from

      $319

      Price per night from

      $319

        0

        Oceanfront contemporary home with stunning island and lighthouse views

        Mid Coast Maine / Southport

        Southport house

        3 6 min stay varies

        • 3 bedrooms
        • sleeps 6
        • min stay varies
        • Child Friendly
        • Car not necessary
        • Air conditioning

        Price per night from

        $220

        Responds fast!
        avg. 1 hour 37 minutes

        Price per night from

        $220

          17

          Cozy_Cottage_Southport_Island

          Mid Coast Maine / Southport

          Southport house

          3 6 min stay varies

          • 3 bedrooms
          • sleeps 6
          • min stay varies
          • Child Friendly
          • Air conditioning

          Price per night from

          $193

          Price per night from

          $193

            21

            Mollys_Cape_Southport

            Mid Coast Maine / Southport

            Southport house

            3 6 min stay varies

            • 3 bedrooms
            • sleeps 6
            • min stay varies
            • Child Friendly
            • Pet Friendly

            Price per night from

            $358

            Price per night from

            $358

              17

              Barnacles_Cottage_Southport

              Mid Coast Maine / Southport

              Southport house

              2 4 min stay varies

              • 2 bedrooms
              • sleeps 4
              • min stay varies
              • Child Friendly
              • Pet Friendly

              Price per night from

              $267

              Price per night from

              $267

                24

                Piffi_Biff_Southport

                Mid Coast Maine / Southport

                Southport house

                5 10 min stay varies

                • 5 bedrooms
                • sleeps 10
                • min stay varies
                • Child Friendly
                • Pet Friendly

                Price per night from

                $296

                Price per night from

                $296

                  21

                  Periwinkle - A Small and Cozy Retreat on Southport Island, Maine

                  Mid Coast Maine / Southport

                  Southport cottage

                  2 4 min stay varies

                  • 2 bedrooms
                  • sleeps 4
                  • min stay varies
                  • Child Friendly

                  Price per night from

                  $163

                  Price per night from

                  $163

                  Great rentals within 20 miles that match your search

                  Distance approx 15.94 km from Southport

                  (3) Excellent 

                    19

                    Mazu, the Bed&Boat, the most waterfront cottage

                    Mid Coast Maine / Damariscotta

                    Damariscotta yacht

                    2 6 2 nights min

                    • 2 bedrooms
                    • sleeps 6
                    • 2 nights min
                    • Beach / lakeside relaxation
                    • Suitable for children age 5+
                    • Car not necessary

                    Price per night from

                    $258

                    Price per night from

                    $258

                    Distance approx 2.8 km from Southport Show on Map

                    (2) Excellent 

                      15

                      New England 1890 House with part water view

                      Mid Coast Maine / Boothbay Harbor

                      Boothbay Harbor apartment

                      1 2 7 nights min

                      • 1 bedroom
                      • sleeps 2
                      • 7 nights min
                      • Nearest beach 8 mi

                      Price per night from

                      $131

                      Price per night from

                      $131

                      Distance approx 18.84 km from Southport

                        20

                        The Barn

                        Mid Coast Maine / Alna

                        Alna house

                        3 12 7 nights min

                        • 3 bedrooms
                        • sleeps 12
                        • 7 nights min
                        • Nearest beach 15 mi
                        • Child Friendly
                        • Air conditioning

                        Price per night from

                        $344

                        Responds fast!
                        avg. 3 hours 13 minutes

                        Price per night from

                        $344

                        Distance approx 12.7 km from Southport

                          27

                          Quahog_Bay_Cottage_ Harpswell

                          Mid Coast Maine / Harpswell

                          Harpswell house

                          3 6 min stay varies

                          • 3 bedrooms
                          • sleeps 6
                          • min stay varies
                          • Child Friendly
                          • Air conditioning

                          Price per night from

                          $268

                          Price per night from

                          $268

                          Distance approx 2.29 km from Southport Show on Map

                            17

                            Ledge_The_Southport

                            Southport / Newagen

                            Newagen house

                            3 4 min stay varies

                            • 3 bedrooms
                            • sleeps 4
                            • min stay varies
                            • Child Friendly

                            Price per night from

                            $333

                            Price per night from

                            $333

                            Distance approx 18.72 km from Southport

                            (5) Excellent 

                              20

                              Ocean Front Cottage, Harpswell, ME

                              Mid Coast Maine / Harpswell

                              Harpswell cottage

                              3 6 7 nights min

                              • 3 bedrooms
                              • sleeps 6
                              • 7 nights min
                              • Beach / lakeside relaxation
                              • Child Friendly
                              • Pet Friendly

                              Price per night from

                              $253

                              Responds fast!
                              avg. 3 hours 9 minutes

                              Price per night from

                              $253

                              Distance approx 4.44 km from Southport

                              (2) Excellent 

                                30

                                Dash_Inn_East_Boothbay

                                Boothbay / East Boothbay

                                East Boothbay house

                                3 6 min stay varies

                                • 3 bedrooms
                                • sleeps 6
                                • min stay varies
                                • Child Friendly
                                • Air conditioning
                                • Pet Friendly

                                Price per night from

                                $255

                                Price per night from

                                $255

                                Distance approx 16.24 km from Southport

                                (2) Very Good 

                                  17

                                  Colorful wonderful Penthouse Apartment

                                  Mid Coast Maine / Brunswick

                                  Brunswick apartment

                                  2 3 4 nights min

                                  • 2 bedrooms
                                  • sleeps 3
                                  • 4 nights min
                                  • Nearest beach 10 mi
                                  • Air conditioning
                                  “This is the Penthouse in the Trees--comfortable, close and convenient to town.” I stayed in the apartment on a long term rental for business needs in Brunswick, from September 2014 to the end of January 2015. I experienced 2 of the seasons in the apa
                                  …see more

                                  Price per night from

                                  $109

                                  Responds fast!
                                  avg. 2 hours 11 minutes

                                  Price per night from

                                  $109

                                  Distance approx 9.3 km from Southport

                                  (7) Very Good 

                                    7

                                    Finch Cottage

                                    Mid Coast Maine / New Harbor

                                    New Harbor house

                                    2 4 7 nights min

                                    • 2 bedrooms
                                    • sleeps 4
                                    • 7 nights min
                                    • Beach / lakeside relaxation
                                    • Child Friendly
                                    • Private garden
                                    “A very enjoyable stay in New Harbor” The Fletchers went out of their way to ensure that we had a good stay at the Finch Cottage. They provided detailed information on things to do and restaurants in the area. They also asked our specific interests a
                                    …see more

                                    Price per night from

                                    $144

                                    Price per night from

                                    $144

                                    Distance approx 7.51 km from Southport

                                      27

                                      Private waterfront home and cabins with trails, dock, kayaks

                                      Mid Coast Maine / South Bristol

                                      South Bristol house

                                      4 8 14 nights min

                                      • 4 bedrooms
                                      • sleeps 8
                                      • 14 nights min
                                      • Nearest beach 14 mi
                                      • Child Friendly
                                      • Pet Friendly

                                      Price per night from

                                      $327

                                      Price per night from

                                      $327

                                      Distance approx 1.27 km from Southport Show on Map

                                        9

                                        OCEAN WAY ON SOUTHPORT ISLAND | QUIET WOODLAND RETREAT NEAR BEACH

                                        Mid Coast Maine / Southport

                                        Southport house

                                        2 4 14 nights min

                                        • 2 bedrooms
                                        • sleeps 4
                                        • 14 nights min
                                        • Ask about children
                                        • Pet Friendly

                                        Price per night from

                                        $164

                                        Price per night from

                                        $164

                                        Distance approx 6.24 km from Southport

                                        (2) Very Good 

                                          14

                                          Maine Cottage, Mid-Coast Maine

                                          Mid Coast Maine / South Bristol

                                          South Bristol cottage

                                          2 4 7 nights min

                                          • 2 bedrooms
                                          • sleeps 4
                                          • 7 nights min
                                          • Beach / lakeside relaxation
                                          • Nearest beach 8 mi
                                          • Child Friendly

                                          Price per night from

                                          $148

                                          Price per night from

                                          $148

                                          Distance approx 16.82 km from Southport

                                            28

                                            Open Ocean Estate

                                            Maine / Bailey Island

                                            Bailey Island house

                                            3 10 7 nights min

                                            • 3 bedrooms
                                            • sleeps 10
                                            • 7 nights min
                                            • Child Friendly
                                            • Private garden

                                            Price per night from

                                            $602

                                            Price per night from

                                            $602

                                            Distance approx 5.22 km from Southport

                                              19

                                              Bluefin_Georgetown

                                              Mid Coast Maine / Georgetown

                                              Georgetown house

                                              2 6 min stay varies

                                              • 2 bedrooms
                                              • sleeps 6
                                              • min stay varies
                                              • Child Friendly

                                              Price per night from

                                              $254

                                              Price per night from

                                              $254

                                              Distance approx 7.91 km from Southport

                                                26

                                                Ocean Waterfront - Walk to Pemaquid Light

                                                Mid Coast Maine / New Harbor

                                                New Harbor house

                                                2 4 7 nights min

                                                • 2 bedrooms
                                                • sleeps 4
                                                • 7 nights min
                                                • Child Friendly

                                                Price per night from

                                                $368

                                                Price per night from

                                                $368

                                                Distance approx 12.36 km from Southport

                                                (2) Excellent 

                                                  18

                                                  A_Lucky_Cast_Westport Island

                                                  Mid Coast Maine / Wiscasset

                                                  Wiscasset house

                                                  4 10 min stay varies

                                                  • 4 bedrooms
                                                  • sleeps 10
                                                  • min stay varies
                                                  • Child Friendly
                                                  • Pet Friendly

                                                  Price per night from

                                                  $308

                                                  Price per night from

                                                  $308

                                                  Distance approx 8.38 km from Southport

                                                  (27) Excellent 

                                                  Certificate of Excellence

                                                    8

                                                    Laughton House & Cottages - Cabin - Low Tide

                                                    Mid Coast Maine / New Harbor

                                                    New Harbor cottage

                                                    1 3 3 nights min

                                                    • 1 bedroom
                                                    • sleeps 3
                                                    • 3 nights min
                                                    • Beach / lakeside relaxation
                                                    • Nearest beach 0.04 mi
                                                    • Child Friendly

                                                    Certificate of Excellence

                                                    Price per night from

                                                    $126

                                                    Responds fast!
                                                    avg. 19 minutes

                                                    Price per night from

                                                    $126

                                                    Distance approx 2.41 km from Southport Show on Map

                                                      20

                                                      Atlantic_Sunset_Boothbay_Harbor

                                                      Mid Coast Maine / Boothbay Harbor

                                                      Boothbay Harbor house

                                                      7 11 min stay varies

                                                      • 7 bedrooms
                                                      • sleeps 11
                                                      • min stay varies
                                                      • Child Friendly
                                                      • Pet Friendly

                                                      Price per night from

                                                      $568

                                                      Price per night from

                                                      $568

                                                      Distance approx 15.83 km from Southport

                                                        17

                                                        Damariscotta waterfront home

                                                        Mid Coast Maine / Damariscotta

                                                        Damariscotta house

                                                        4 7 4 nights min

                                                        • 4 bedrooms
                                                        • sleeps 7
                                                        • 4 nights min
                                                        • Child Friendly

                                                        Price per night from

                                                        $556

                                                        Price per night from

                                                        $556

                                                        Distance approx 3.13 km from Southport Show on Map

                                                        (1) Excellent 

                                                          13

                                                          Waterfront luxury home in Georgetown Maine

                                                          Mid Coast Maine / Georgetown

                                                          Georgetown house

                                                          4 9 7 nights min

                                                          • 4 bedrooms
                                                          • sleeps 9
                                                          • 7 nights min
                                                          • Ask about children
                                                          • Ask about pets

                                                          Price per night from

                                                          $982

                                                          Price per night from

                                                          $982

                                                          Distance approx 4.35 km from Southport

                                                            69

                                                            Spectacular Views! 800 deep water feet, 3.5 acres!

                                                            Mid Coast Maine / Wiscasset

                                                            Wiscasset cottage

                                                            5 12 3 nights min

                                                            • 5 bedrooms
                                                            • sleeps 12
                                                            • 3 nights min
                                                            • Child Friendly
                                                            • Private garden

                                                            Price per night from

                                                            $1,140

                                                            Price per night from

                                                            $1,140

                                                            Distance approx 8.15 km from Southport

                                                              22

                                                              The Artist's Box : An Adorable Ocean Front Cottage

                                                              Mid Coast Maine / New Harbor

                                                              New Harbor cottage

                                                              3 5 7 nights min

                                                              • 3 bedrooms
                                                              • sleeps 5
                                                              • 7 nights min
                                                              • Private garden

                                                              Price per night from

                                                              $385

                                                              Price per night from

                                                              $385

                                                              Distance approx 19.02 km from Southport

                                                              (3) Excellent 

                                                                27

                                                                Private Island - Great for Reunions - Sleeps 24

                                                                Mid Coast Maine / Port Clyde

                                                                Port Clyde house

                                                                11 24 7 nights min

                                                                • 11 bedrooms
                                                                • sleeps 24
                                                                • 7 nights min
                                                                • Beach / lakeside relaxation
                                                                • Child Friendly
                                                                • Pet Friendly

                                                                Price per night from

                                                                $2,453

                                                                Price per night from

                                                                $2,453

                                                                Distance approx 8.38 km from Southport

                                                                (5) Excellent 

                                                                  10

                                                                  Laughton House & Cottages - High Tide Cabin

                                                                  Mid Coast Maine / New Harbor

                                                                  New Harbor cottage

                                                                  1 3 3 nights min

                                                                  • 1 bedroom
                                                                  • sleeps 3
                                                                  • 3 nights min
                                                                  • Nearest beach 0.06 mi
                                                                  • Child Friendly

                                                                  Price per night from

                                                                  $126

                                                                  Responds fast!
                                                                  avg. 19 minutes

                                                                  Price per night from

                                                                  $126

                                                                  Distance approx 7.63 km from Southport

                                                                    17

                                                                    SUNRISE | BOOTHBAY | WATER VIEWS | DOCK & FLOAT | VIEWS OF OVENS MOUTH | PET-FRI

                                                                    Mid Coast Maine / Boothbay

                                                                    Boothbay house

                                                                    1 2 4 nights min

                                                                    • 1 bedroom
                                                                    • sleeps 2
                                                                    • 4 nights min
                                                                    • Ask about children
                                                                    • Air conditioning
                                                                    • Pet Friendly

                                                                    Price per night from

                                                                    $288

                                                                    Price per night from

                                                                    $288

                                                                    Distance approx 1.23 km from Southport Show on Map

                                                                      17

                                                                      SOUTHPORT Waterfront Tidewater Farm with dock

                                                                      Mid Coast Maine / Boothbay Harbor

                                                                      Boothbay Harbor farmhouse

                                                                      4 5 7 nights min

                                                                      • 4 bedrooms
                                                                      • sleeps 5
                                                                      • 7 nights min
                                                                      • Beach / lakeside relaxation
                                                                      • Nearest beach 2 mi
                                                                      • Child Friendly

                                                                      Price per night from

                                                                      $573

                                                                      Price per night from

                                                                      $573

                                                                      Distance approx 2.85 km from Southport Show on Map

                                                                        25

                                                                        NEW! Boothbay Harbor Cabin w/Spacious Deck & Yard!

                                                                        Mid Coast Maine / Boothbay Harbor

                                                                        Boothbay Harbor cottage

                                                                        3 8 min stay varies

                                                                        • 3 bedrooms
                                                                        • sleeps 8
                                                                        • min stay varies
                                                                        • Child Friendly

                                                                        Price per night from

                                                                        $229

                                                                        Responds fast!
                                                                        avg. 9 minutes

                                                                        Price per night from

                                                                        $229

                                                                        Distance approx 14.31 km from Southport

                                                                          14

                                                                          The Point, Where the Land Meets the Sea

                                                                          Mid Coast Maine / Harpswell

                                                                          Harpswell house

                                                                          4 8 min stay varies

                                                                          • 4 bedrooms
                                                                          • sleeps 8
                                                                          • min stay varies
                                                                          • Child Friendly
                                                                          • Pet Friendly

                                                                          Price per night from

                                                                          $524

                                                                          Price per night from

                                                                          $524

                                                                          Distance approx 8.86 km from Southport

                                                                          (6) Excellent 

                                                                            21

                                                                            Victorian Cottage on Westport Island

                                                                            Mid Coast Maine / Wiscasset

                                                                            Wiscasset cottage

                                                                            4 8 3 nights min

                                                                            • 4 bedrooms
                                                                            • sleeps 8
                                                                            • 3 nights min
                                                                            • Beach / lakeside relaxation
                                                                            • Child Friendly
                                                                            • Private garden

                                                                            Price per night from

                                                                            $229

                                                                            Price per night from

                                                                            $229

                                                                            Distance approx 13.16 km from Southport

                                                                            (8) Excellent 

                                                                              16

                                                                              Cozy 2-bdrm w/ lg deck overlooking Round Pond cove

                                                                              Mid Coast Maine / Round Pond

                                                                              Round Pond house

                                                                              2 4 7 nights min

                                                                              • 2 bedrooms
                                                                              • sleeps 4
                                                                              • 7 nights min
                                                                              • Beach / lakeside relaxation
                                                                              • Child Friendly
                                                                              • Pet Friendly

                                                                              Price per night from

                                                                              $75

                                                                              Price per night from

                                                                              $75