check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag
Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Islesboro Island: Houses, Cottages & More (300+)

  • 1 - 50 of 300+
Additional fees apply. Taxes may be added.
    • 3 BR
    • 1 BA
    • 1 HF BA
    • Sleeps 9
    House #147060
    2 Reviews
      • 2 BR
      • 1 BA
      • Sleeps 5
      Cottage #178936
      15
        avg/night
        • 3 BR
        • 1 HF BA
        • Sleeps 8
        Barn #412090vb
        Viewed 11 times in the last 48 hours
          • 4 BR
          • 1 BA
          • 1 HF BA
          • Sleeps 8
          Cottage #158754
            Wonderful! 4.9/5
            (16 reviews)
            avg/night
            • 5 BR
            • 2 BA
            • Sleeps 9
            House #30315vb
            16
            Viewed 17 times in the last 48 hours
              Excellent! 4.4/5
              (5 reviews)
              avg/night
              • 4 BR
              • 2 BA
              • Sleeps 10
              Farmhouse #762747vb
              5
              Viewed 9 times in the last 48 hours
                Wonderful! 4.8/5
                (9 reviews)
                avg/night
                • 3 BR
                • 2 BA
                • Sleeps 6
                House #4242587
                9
                Viewed 5 times in the last 48 hours
                  Wonderful! 4.9/5
                  (15 reviews)
                  avg/night
                  • 8 BR
                  • 6 BA
                  • 1 HF BA
                  • Sleeps 16
                  House #130513
                  15
                  Viewed 16 times in the last 48 hours
                    • 6 BR
                    • 2 BA
                    • Sleeps 12
                    House #384600vb
                    1 Review
                      • 6 BR
                      • 3 BA
                      • 1 HF BA
                      • Sleeps 14
                      House #564626vb
                      4
                        Exceptional! 5.0/5
                        (6 reviews)
                        $80
                        avg/night
                        • 1 BR
                        • 1 BA
                        • Sleeps 2
                        Barn #791107vb
                        6
                        Viewed 11 times in the last 48 hours
                          • 2 BR
                          • 2 BA
                          • Sleeps 6
                          Apartment #125747
                          10
                            Wonderful! 4.9/5
                            (17 reviews)
                            avg/night
                            • 3 BR
                            • 2 BA
                            • Sleeps 8
                            Apartment #146785
                            17
                            Viewed 11 times in the last 48 hours
                              Exceptional! 5.0/5
                              (10 reviews)
                              $61
                              avg/night
                              • 1 BR
                              • 1 BA
                              • Sleeps 4
                              Apartment #267979
                              10
                              Viewed 6 times in the last 48 hours
                                • 3 BR
                                • 1 BA
                                • 1 HF BA
                                • Sleeps 5
                                Apartment #474102vb
                                30
                                  • 3 BR
                                  • 1 BA
                                  • 1 HF BA
                                  • Sleeps 6
                                  House #3692712
                                  14
                                    Exceptional! 5.0/5
                                    (9 reviews)
                                    avg/night
                                    • 4 BR
                                    • 2 BA
                                    • Sleeps 8
                                    Cottage #560935vb
                                    9
                                    Viewed 5 times in the last 48 hours
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 2
                                      Apartment #3925440
                                      1 Review
                                        Exceptional! 5.0/5
                                        (5 reviews)
                                        avg/night
                                        • 2 BR
                                        • 2 BA
                                        • Sleeps 4
                                        Cottage #779354vb
                                        5
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 8
                                          House #582537vb
                                          27
                                            • 2 BR
                                            • 2 BA
                                            • Sleeps 6
                                            Cottage #3925835
                                            10
                                              Wonderful! 4.8/5
                                              (9 reviews)
                                              avg/night
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 3
                                              Cottage #3772903
                                              9
                                              Viewed 7 times in the last 48 hours
                                                • 1 BR
                                                • 1 BA
                                                • Sleeps 2
                                                Studio #579493vb
                                                4
                                                  • 3 BR
                                                  • 2 BA
                                                  • 1 HF BA
                                                  • Sleeps 6
                                                  Cottage #3968158
                                                  1 Review
                                                    • 4 BR
                                                    • 2 BA
                                                    • 1 HF BA
                                                    • Sleeps 10
                                                    House #4142348
                                                    10
                                                      Exceptional! 5.0/5
                                                      (15 reviews)
                                                      avg/night
                                                      • 2 BR
                                                      • 1 BA
                                                      • Sleeps 6
                                                      Apartment #152137
                                                      15
                                                      Viewed 10 times in the last 48 hours
                                                        • 2 BR
                                                        • 1 BA
                                                        • 1 HF BA
                                                        • Sleeps 6
                                                        House #696594vb
                                                        2 Reviews
                                                          Excellent! 4.7/5
                                                          (22 reviews)
                                                          avg/night
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 5
                                                          House #3754964
                                                          22
                                                          Viewed 12 times in the last 48 hours
                                                            Wonderful! 4.9/5
                                                            (57 reviews)
                                                            avg/night
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 2
                                                            Apartment #325925
                                                            57
                                                            Viewed 10 times in the last 48 hours
                                                              Wonderful! 4.8/5
                                                              (6 reviews)
                                                              avg/night
                                                              • 4 BR
                                                              • 3 BA
                                                              • Sleeps 10
                                                              House #835052vb
                                                              6
                                                              Viewed 7 times in the last 48 hours
                                                                • 3 BR
                                                                • 2 BA
                                                                • Sleeps 6
                                                                House #802225vb
                                                                7
                                                                  Exceptional! 5.0/5
                                                                  (22 reviews)
                                                                  $86
                                                                  avg/night
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 5
                                                                  Apartment #165030vb
                                                                  22
                                                                  Viewed 6 times in the last 48 hours
                                                                    Exceptional! 5.0/5
                                                                    (22 reviews)
                                                                    avg/night
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 3
                                                                    House #180885vb
                                                                    22
                                                                      avg/night
                                                                      • 4 BR
                                                                      • 3 BA
                                                                      • Sleeps 10
                                                                      House #803429vb
                                                                      2 Reviews
                                                                      Viewed 7 times in the last 48 hours
                                                                        • 5 BR
                                                                        • 5 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 12
                                                                        House #927721vb
                                                                        Viewed 9 times in the last 48 hours
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 2
                                                                          Apartment #3515291
                                                                          36
                                                                            Wonderful! 4.9/5
                                                                            (18 reviews)
                                                                            $86
                                                                            avg/night
                                                                            • 3 BR
                                                                            • 1 BA
                                                                            • 1 HF BA
                                                                            • Sleeps 8
                                                                            Cabin #3864196
                                                                            18
                                                                            Viewed 10 times in the last 48 hours
                                                                              • 4 BR
                                                                              • 3 BA
                                                                              • Sleeps 10
                                                                              House #721875vb
                                                                              3
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 8
                                                                                House #859446vb
                                                                                3
                                                                                  Wonderful! 4.9/5
                                                                                  (12 reviews)
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 3 BA
                                                                                  • Sleeps 7
                                                                                  House #840063vb
                                                                                  12
                                                                                    • Studio
                                                                                    • 1 BA
                                                                                    • Sleeps 2
                                                                                    Studio #599202vb
                                                                                    6
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • 1 HF BA
                                                                                      • Sleeps 6
                                                                                      House #3942852
                                                                                      9
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 8
                                                                                        House #329873vb
                                                                                        16
                                                                                          Wonderful! 4.9/5
                                                                                          (16 reviews)
                                                                                          avg/night
                                                                                          • 4 BR
                                                                                          • 2 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 8
                                                                                          Townhome #460796vb
                                                                                          16
                                                                                            Wonderful! 4.9/5
                                                                                            (18 reviews)
                                                                                            avg/night
                                                                                            • 4 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 8
                                                                                            House #692157vb
                                                                                            18
                                                                                            Viewed 6 times in the last 48 hours
                                                                                              • 4 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 10
                                                                                              House #4153148
                                                                                              6
                                                                                                Excellent! 4.5/5
                                                                                                (6 reviews)
                                                                                                $62
                                                                                                avg/night
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 2
                                                                                                Studio #4210882
                                                                                                6
                                                                                                Viewed 6 times in the last 48 hours
                                                                                                  Exceptional! 5.0/5
                                                                                                  (9 reviews)
                                                                                                  avg/night
                                                                                                  • 5 BR
                                                                                                  • 3 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 20
                                                                                                  House #326138vb
                                                                                                  9
                                                                                                  Viewed 6 times in the last 48 hours
                                                                                                    • 4 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 6
                                                                                                    Cottage #494758vb
                                                                                                    17
                                                                                                      • 2 BR
                                                                                                      • 1 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 4
                                                                                                      House #678066vb
                                                                                                      3
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Islesboro Island Reviews

                                                                                                      A wonderful and cozy apartment located in a welcoming and cozy seaside town.

                                                                                                      5 of 5
                                                                                                      My Wife and I thoroughly enjoyed our extended stay at this well furnished, warm and comfortable upstairs apartment. The gas fireplace added atmosphere. The owner was great to work with and accommodating. It is conveniently located across from a great brewpub and a very nice restaurant. It was within walking distance to a park overlooking the inlet and near several nice shops. Blue Hill is located near Bar Harbor and the National Park. I look forward to our return visit and without hesitation recommend it to others.
                                                                                                      • Submitted: Dec 6, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      An amazing stay in a truly unique home!

                                                                                                      5 of 5
                                                                                                      Doug and Leah, We enjoyed your wonderful, comfortable, interesting and unique home so very much! My husband and daughter loved the furnishings, comfortable beds and bedding and all the unique items (owls, heart stones, antiques) that make this rental one of a kind. Right down the road is the Owls Head Light House and a quintessential little fishing harbor with lobster boats and traps. Our daughter loved sleeping in the bunks in the cupola! What an experience. We woke early to watch the sunrise from up there....and then went back to peaceful sleep. Thank you for sharing your unique home in its magical place. We've told so many friends about your home, though I'd like to keep it my secret place. 😊򒠠We will be back for sure!
                                                                                                      • Submitted: Dec 1, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Exactly like the photos!

                                                                                                      5 of 5
                                                                                                      Convenient and quaint. The owners were kind and the space very comfortable. We loved the tips for the best sunrise and bites to eat in town. Will definitely be coming back.
                                                                                                      • Submitted: Nov 7, 2016
                                                                                                      • Stayed: Oct 2016