Bailey Island Rentals

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144 Houses

    26

    Historic Captain York House: 7 Bed, 6.5 Bath

    Maine / Bailey Island

    Bailey Island house

    7 14 7 nights min

    • 7 bedrooms
    • sleeps 14
    • 7 nights min
    • Child Friendly

    Price per night from

    $567

    Price per night from

    $567

      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

      $604

      Price per night from

      $604

      Great rentals within 20 miles that match your search

      Distance approx 6.92 km from Bailey Island

      (4) Excellent 

        29

        Spectacular Ocean Views & Private Beach, Minutes from Popham & Sebasco Resort

        Mid Coast Maine / Phippsburg

        Phippsburg house

        3 8 7 nights min

        • 3 bedrooms
        • sleeps 8
        • 7 nights min
        • Child Friendly
        • Pet Friendly
        • Private garden

        Price per night from

        $227

        Price per night from

        $227

        Distance approx 13.72 km from Bailey Island

          43

          Old Port Style & Luxury

          Maine / Portland

          Portland apartment

          3 6 min stay varies

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

          Price per night from

          $203

          Responds fast!
          avg. 2 hours 29 minutes

          Price per night from

          $203

          Distance approx 18.15 km from Bailey Island

          (2) Excellent 

            8

            Higgins Beach Maine

            Maine / Scarborough

            Scarborough cottage

            4 8 1 night min

            • 4 bedrooms
            • sleeps 8
            • 1 night min
            • Beach / lakeside relaxation
            • Child Friendly
            • Car not necessary

            Price per night from

            $288

            Price per night from

            $288

            Distance approx 12.83 km from Bailey Island

            (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

              $110

              Responds fast!
              avg. 2 hours 11 minutes

              Price per night from

              $110

              Distance approx 8.33 km from Bailey Island

              (1) Excellent 

                12

                Goose Cove - Spacious Water Front with Stunning Views, 5 Bed, 3.5 Bath

                Maine / Freeport

                Freeport house

                5 12 3 nights min

                • 5 bedrooms
                • sleeps 12
                • 3 nights min
                • Nearest beach 9 mi
                • Child Friendly
                • Private garden

                Price per night from

                $800

                Responds fast!
                avg. 2 hours 45 minutes

                Price per night from

                $800

                Distance approx 9.57 km from Bailey Island

                  30

                  Open and Modern 3BR Yarmouth Home, Bikes Provided!

                  Maine / Yarmouth

                  Yarmouth house

                  3 6 3 nights min

                  • 3 bedrooms
                  • sleeps 6
                  • 3 nights min
                  • Ski
                  • Child Friendly

                  Price per night from

                  $294

                  Responds fast!
                  avg. 21 minutes

                  Price per night from

                  $294

                  Distance approx 10.46 km from Bailey Island

                    42

                    Portland Area Cottage w/OCEAN VIEWS ~ pet friendly

                    Maine / Falmouth

                    Falmouth house

                    3 6 2 nights min

                    • 3 bedrooms
                    • sleeps 6
                    • 2 nights min
                    • Beach / lakeside relaxation
                    • Child Friendly
                    • Car not necessary

                    Price per night from

                    $570

                    Responds fast!
                    avg. 2 hours 40 minutes

                    Price per night from

                    $570

                    Distance approx 1.42 km from Bailey Island

                    (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

                      $255

                      Responds fast!
                      avg. 3 hours 13 minutes

                      Price per night from

                      $255

                      Distance approx 11.1 km from Bailey Island

                      (2) Average 

                        23

                        Oceanfront Cottage with private beach-Pet friendly

                        Mid Coast Maine / West Bath

                        West Bath house

                        3 8 7 nights min

                        • 3 bedrooms
                        • sleeps 8
                        • 7 nights min
                        • Beach / lakeside relaxation
                        • Nearest beach 0 mi
                        • Child Friendly

                        Price per night from

                        $165

                        Price per night from

                        $165

                        Distance approx 12.85 km from Bailey Island

                        (3) Excellent 

                          72

                          WILLARD BEACH with OCEAN VIEWS ~ 100 yds to beach!

                          Maine / South Portland

                          South Portland house

                          3 9 min stay varies

                          • 3 bedrooms
                          • sleeps 9
                          • min stay varies
                          • Child Friendly
                          • Air conditioning
                          • Pet Friendly

                          Price per night from

                          $339

                          Responds fast!
                          avg. 2 hours 40 minutes

                          Price per night from

                          $339

                          Distance approx 19 km from Bailey Island

                            15

                            Quiet Lake Serenity Just 10 Miles from Portland

                            Maine / Windham

                            Windham house

                            3 8 7 nights min

                            • 3 bedrooms
                            • sleeps 8
                            • 7 nights min
                            • Child Friendly
                            • Private garden

                            Price per night from

                            $312

                            Price per night from

                            $312

                            Distance approx 13.26 km from Bailey Island

                              15

                              Luxurious, Fully Renovated house with Private Beach rights.

                              Maine / Cape Elizabeth

                              Cape Elizabeth house

                              5 10 min stay varies

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

                              Price per night from

                              $570

                              Responds fast!
                              avg. 2 hours 40 minutes

                              Price per night from

                              $570

                              Distance approx 15.99 km from Bailey Island

                                25

                                MERWICK COTTAGE | GEORGETOWN, MAINE |WATERFRONT | PRIVATE DOCK AND FLOAT

                                Mid Coast Maine / Georgetown

                                Georgetown house

                                3 6 4 nights min

                                • 3 bedrooms
                                • sleeps 6
                                • 4 nights min
                                • Ask about children
                                • Pet Friendly

                                Price per night from

                                $346

                                Price per night from

                                $346

                                Distance approx 18.5 km from Bailey Island

                                  105

                                  Spectacular Views! Vintage waterfront Cottage!!

                                  Mid Coast Maine / Wiscasset

                                  Wiscasset house

                                  5 12 3 nights min

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

                                  Price per night from

                                  $1,144

                                  Responds fast!
                                  avg. 9 minutes

                                  Price per night from

                                  $1,144

                                  Distance approx 15.36 km from Bailey Island

                                    24

                                    Close to EVERYTHING!

                                    Maine / Portland

                                    Portland apartment

                                    3 8 3 nights min

                                    • 3 bedrooms
                                    • sleeps 8
                                    • 3 nights min
                                    • Child Friendly
                                    • Pet Friendly
                                    • Private garden

                                    Price per night from

                                    $230

                                    Price per night from

                                    $230

                                    Distance approx 15.82 km from Bailey Island

                                      23

                                      Waterfront House with Views of Working Harbor and Open Ocean from Every Room

                                      Mid Coast Maine / Georgetown

                                      Georgetown house

                                      4 7 7 nights min

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

                                      Price per night from

                                      $324

                                      Price per night from

                                      $324

                                      Distance approx 8.48 km from Bailey Island

                                        24

                                        NEW! ‘Osprey Cottage’ 2BR South Freeport Cottage

                                        Maine / South Freeport

                                        South Freeport cottage

                                        2 6 min stay varies

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

                                        Price per night from

                                        $286

                                        Responds fast!
                                        avg. 9 minutes

                                        Price per night from

                                        $286

                                        Distance approx 10.94 km from Bailey Island

                                          24

                                          NEW! Updated Freeport House w/Porch Near Downtown!

                                          Maine / Freeport

                                          Freeport house

                                          3 6 min stay varies

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

                                          Price per night from

                                          $173

                                          Responds fast!
                                          avg. 9 minutes

                                          Price per night from

                                          $173

                                          Distance approx 12.86 km from Bailey Island

                                          (3) Excellent 

                                            12

                                            Executive furnished Penthouse in Brunswick, Maine.

                                            Mid Coast Maine / Brunswick

                                            Brunswick apartment

                                            1 2 7 nights min

                                            • 1 bedroom
                                            • sleeps 2
                                            • 7 nights min
                                            • Nearest beach 30 mi
                                            • Air conditioning
                                            • Pet Friendly
                                            “Great interior, great location, great landlord!” The penthouse is tastefully furnished with a spacious yet cozy layout, with the bed area out of sight of the living room and kitchen. The bathroom is small but very nice. Comes with a large television a
                                            …see more

                                            Price per night from

                                            $92

                                            Responds fast!
                                            avg. 2 hours 11 minutes

                                            Price per night from

                                            $92

                                            Distance approx 18.62 km from Bailey Island

                                              31

                                              SOUTHPORT waterfront historic farmhouse w dock

                                              Mid Coast Maine / Boothbay Harbor

                                              Boothbay Harbor house

                                              4 5 7 nights min

                                              • 4 bedrooms
                                              • sleeps 5
                                              • 7 nights min
                                              • Nearest beach 2 mi
                                              • Child Friendly
                                              • Private garden

                                              Price per night from

                                              $575

                                              Price per night from

                                              $575

                                              Distance approx 19.5 km from Bailey Island

                                              (45) Excellent 

                                                27

                                                Boothbay Harbor Pet-Friendly High-Tech House Lake Access Near Ocean

                                                Mid Coast Maine / Boothbay Harbor

                                                Boothbay Harbor cottage

                                                3 6 2 nights min

                                                • 3 bedrooms
                                                • sleeps 6
                                                • 2 nights min
                                                • Beach / lakeside relaxation
                                                • Nearest beach 3 mi
                                                • Child Friendly
                                                “What a great place to stay!” We stayed in the Lake View Cottage. The description doesn't do it justice and we loved it up there. Our son was especially excited that the beach was right across the way and that there was a little boy in Ocean View Cotta
                                                …see more

                                                Price per night from

                                                $226

                                                Price per night from

                                                $226

                                                Distance approx 12.92 km from Bailey Island

                                                  63

                                                  NEW LISTING: Stunningly Renovated Beach House with OCEAN VIEWS-150 yds to beach

                                                  Maine / South Portland

                                                  South Portland house

                                                  4 13 min stay varies

                                                  • 4 bedrooms
                                                  • sleeps 13
                                                  • min stay varies
                                                  • Child Friendly
                                                  • Air conditioning
                                                  • Private garden

                                                  Price per night from

                                                  $684

                                                  Responds fast!
                                                  avg. 2 hours 40 minutes

                                                  Price per night from

                                                  $684

                                                  Distance approx 15.18 km from Bailey Island

                                                    19

                                                    Panoramic Ocean Views!

                                                    Maine / Cape Elizabeth

                                                    Cape Elizabeth house

                                                    2 6 7 nights min

                                                    • 2 bedrooms
                                                    • sleeps 6
                                                    • 7 nights min
                                                    • Child Friendly
                                                    • Air conditioning
                                                    • Ask about pets

                                                    Price per night from

                                                    $460

                                                    Price per night from

                                                    $460

                                                    Distance approx 16.83 km from Bailey Island

                                                      24

                                                      NEW! Cozy Westbrook Apt w/Fire Pit- Near Portland!

                                                      Maine / Westbrook

                                                      Westbrook apartment

                                                      1 6 min stay varies

                                                      • 1 bedroom
                                                      • sleeps 6
                                                      • min stay varies
                                                      • Ski
                                                      • Child Friendly
                                                      • Air conditioning

                                                      Price per night from

                                                      $68

                                                      Responds fast!
                                                      avg. 58 minutes

                                                      Price per night from

                                                      $68

                                                      Distance approx 19.31 km from Bailey Island

                                                        14

                                                        Capitol Retreat - An Impressive Boothbay Harbor Vacation Home

                                                        Mid Coast Maine / Boothbay Harbor

                                                        Boothbay Harbor house

                                                        4 8 min stay varies

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

                                                        Price per night from

                                                        $262

                                                        Price per night from

                                                        $262

                                                        Distance approx 15.83 km from Bailey Island

                                                          21

                                                          Enjoy a Secluded Location on Mount Desert

                                                          Mount Desert Island / Mount Desert

                                                          Mount Desert house

                                                          3 8 7 nights min

                                                          • 3 bedrooms
                                                          • sleeps 8
                                                          • 7 nights min
                                                          • Swimming pool
                                                          • Child Friendly
                                                          • Air conditioning

                                                          Price per night from

                                                          $329

                                                          Price per night from

                                                          $329

                                                          Distance approx 13.1 km from Bailey Island

                                                            71

                                                            WILLARD BEACH: Stunning newly RENOVATED HOUSE! 4 Mins to DT Portland.

                                                            Maine / Portland

                                                            Portland house

                                                            4 9 min stay varies

                                                            • 4 bedrooms
                                                            • sleeps 9
                                                            • min stay varies
                                                            • Nearest beach 0 mi
                                                            • Child Friendly

                                                            Price per night from

                                                            $570

                                                            Responds fast!
                                                            avg. 2 hours 40 minutes

                                                            Price per night from

                                                            $570

                                                            Distance approx 11.1 km from Bailey Island

                                                              29

                                                              Pet Friendly West Bath Home w/Dock, Beach & Canoe!

                                                              Mid Coast Maine / Harpswell

                                                              Harpswell cottage

                                                              3 8 min stay varies

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

                                                              Price per night from

                                                              $127

                                                              Responds fast!
                                                              avg. 21 minutes

                                                              Price per night from

                                                              $127

                                                              Distance approx 13.23 km from Bailey Island

                                                                4

                                                                Portland Maine East End - Top of Munjoy Hill (30 day minimum stay)

                                                                Maine / Portland

                                                                Portland apartment

                                                                2 4 30 nights min

                                                                • 2 bedrooms
                                                                • sleeps 4
                                                                • 30 nights min
                                                                • Child Friendly
                                                                • Air conditioning

                                                                Price per night from

                                                                $115

                                                                Price per night from

                                                                $115

                                                                Distance approx 13.49 km from Bailey Island

                                                                  33

                                                                  Furnished & newly built Modern Cottage, walk to the ocean, 10 min to Portland

                                                                  Maine / Cape Elizabeth

                                                                  Cape Elizabeth house

                                                                  2 4 min stay varies

                                                                  • 2 bedrooms
                                                                  • sleeps 4
                                                                  • min stay varies
                                                                  • Air conditioning
                                                                  • Private garden

                                                                  Price per night from

                                                                  $230

                                                                  Price per night from

                                                                  $230

                                                                  Distance approx 18.75 km from Bailey Island

                                                                    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

                                                                    $164

                                                                    Price per night from

                                                                    $164

                                                                    Distance approx 7.45 km from Bailey Island

                                                                    (9) Very Good 

                                                                      17

                                                                      Minutes from Popham Beach - Cozy Maine Coast Cottage

                                                                      Mid Coast Maine / Phippsburg

                                                                      Phippsburg cottage

                                                                      3 6 min stay varies

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

                                                                      Price per night from

                                                                      $219

                                                                      Price per night from

                                                                      $219

                                                                      Distance approx 12.34 km from Bailey Island

                                                                      (9) Excellent 

                                                                        16

                                                                        Beachfront Cottage on Indian Point

                                                                        Mid Coast Maine / Georgetown

                                                                        Georgetown cottage

                                                                        2 6 7 nights min

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

                                                                        Price per night from

                                                                        $281

                                                                        Price per night from

                                                                        $281

                                                                        Distance approx 19.05 km from Bailey Island

                                                                        (1) Excellent 

                                                                          26

                                                                          LUXURY PRIVATE BEACH KAYAKS/SUP/CANOE/SWIM,60' SMART TV,BOOTHBAY, FREEPORT, MORE

                                                                          Mid Coast Maine / Bath

                                                                          Bath house

                                                                          5 11 min stay varies

                                                                          • 5 bedrooms
                                                                          • sleeps 11
                                                                          • min stay varies
                                                                          • Beach / lakeside relaxation
                                                                          • Child Friendly
                                                                          • Air conditioning

                                                                          Price per night from

                                                                          $502

                                                                          Price per night from

                                                                          $502

                                                                          Distance approx 13.08 km from Bailey Island

                                                                          (8) Excellent 

                                                                            22

                                                                            Georgetown (Back River) Vacation Home

                                                                            Mid Coast Maine / Georgetown

                                                                            Georgetown house

                                                                            5 10 7 nights min

                                                                            • 5 bedrooms
                                                                            • sleeps 10
                                                                            • 7 nights min
                                                                            • Beach / lakeside relaxation
                                                                            • Child Friendly
                                                                            • Pet Friendly

                                                                            Price per night from

                                                                            $282

                                                                            Responds fast!
                                                                            avg. 3 hours 39 minutes

                                                                            Price per night from

                                                                            $282

                                                                            Distance approx 11.21 km from Bailey Island

                                                                            (1) Excellent 

                                                                              11

                                                                              Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch

                                                                              Maine / Peaks Island

                                                                              Peaks Island cottage

                                                                              4 8 3 nights min

                                                                              • 4 bedrooms
                                                                              • sleeps 8
                                                                              • 3 nights min
                                                                              • Child Friendly

                                                                              Price per night from

                                                                              $461

                                                                              Responds fast!
                                                                              avg. 2 hours 51 minutes

                                                                              Price per night from

                                                                              $461