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Drakes Island: Houses, Cottages & More (900+)

  • 1 - 50 of 900+
Additional fees apply. Taxes may be added.
    • 4 BR
    • 3 BA
    • Sleeps 8
    2 Reviews
      • 4 BR
      • 2 BA
      • Sleeps 8
        NEW!
        • 4 BR
        • 3 BA
        • 1 HF BA
        • Sleeps 8
        1 Review
          • 7 BR
          • 2 BA
          • Sleeps 10
          2 Reviews
            • 2 BR
            • 1 BA
            • Sleeps 8
              • 3 BR
              • 3 BA
              • Sleeps 10
                Wonderful! 4.9/5
                (20 reviews)
                $81
                avg/night
                • 1 BR
                • 1 BA
                • Sleeps 3
                20
                  Exceptional! 5.0/5
                  (7 reviews)
                  avg/night
                  • 3 BR
                  • 2 BA
                  • Sleeps 10
                  7
                    NEW!
                    • 2 BR
                    • 1 BA
                    • Sleeps 6
                      • 2 BR
                      • 2 BA
                      • Sleeps 6
                      1 Review
                        • Studio
                        • 2 BA
                        • 1 HF BA
                        • Sleeps 8
                        2 Reviews
                          • 1 BR
                          • 1 BA
                          • Sleeps 4
                          6
                            Wonderful! 4.8/5
                            (19 reviews)
                            avg/night
                            • 3 BR
                            • 2 BA
                            • 1 HF BA
                            • Sleeps 11
                            19
                              Wonderful! 4.9/5
                              (7 reviews)
                              avg/night
                              • 3 BR
                              • 1 BA
                              • 1 HF BA
                              • Sleeps 8
                              7
                                Exceptional! 5.0/5
                                (10 reviews)
                                avg/night
                                • 2 BR
                                • 1 BA
                                • Sleeps 6
                                10
                                  Wonderful! 4.9/5
                                  (8 reviews)
                                  $95
                                  avg/night
                                  • Studio
                                  • 1 BA
                                  • Sleeps 2
                                  8
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 7
                                    6
                                      NEW!
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 6
                                      2 Reviews
                                        • 2 BR
                                        • 1 BA
                                        • Sleeps 6
                                        3
                                          Wonderful! 4.8/5
                                          (13 reviews)
                                          avg/night
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 6
                                          13
                                            • Studio
                                            • 1 BA
                                            • Sleeps 6
                                            2 Reviews
                                              Excellent! 4.5/5
                                              (6 reviews)
                                              avg/night
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 2
                                              6
                                                Very Good! 4.0/5
                                                (6 reviews)
                                                avg/night
                                                • 3 BR
                                                • 1 BA
                                                • Sleeps 8
                                                6
                                                  • 2 BR
                                                  • 1 BA
                                                  • Sleeps 5
                                                  4
                                                    Excellent! 4.6/5
                                                    (5 reviews)
                                                    avg/night
                                                    • 3 BR
                                                    • 1 BA
                                                    • Sleeps 6
                                                    5
                                                      Exceptional! 5.0/5
                                                      (7 reviews)
                                                      avg/night
                                                      • 2 BR
                                                      • 1 BA
                                                      • Sleeps 5
                                                      7
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 4
                                                        3
                                                          • 2 BR
                                                          • 1 BA
                                                          • Sleeps 6
                                                          5
                                                            • 2 BR
                                                            • 1 BA
                                                            • Sleeps 8
                                                            5
                                                              • 3 BR
                                                              • 1 BA
                                                              • Sleeps 8
                                                              2 Reviews
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 6
                                                                1 Review
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 4
                                                                  3
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 4
                                                                    3
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      8
                                                                        • 3 BR
                                                                        • 1 BA
                                                                        • Sleeps 6
                                                                        5
                                                                          Exceptional! 5.0/5
                                                                          (6 reviews)
                                                                          avg/night
                                                                          • 6 BR
                                                                          • 3 BA
                                                                          • 1 HF BA
                                                                          • Sleeps 12
                                                                          6
                                                                            • 3 BR
                                                                            • 3 BA
                                                                            • 1 HF BA
                                                                            • Sleeps 6
                                                                              Wonderful! 4.9/5
                                                                              (7 reviews)
                                                                              avg/night
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              7
                                                                                • 4 BR
                                                                                • 2 BA
                                                                                • Sleeps 8
                                                                                2 Reviews
                                                                                  • 2 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 7
                                                                                  8
                                                                                    • 5 BR
                                                                                    • 1 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 10
                                                                                    9
                                                                                      Excellent! 4.4/5
                                                                                      (11 reviews)
                                                                                      avg/night
                                                                                      • 4 BR
                                                                                      • 2 BA
                                                                                      • 1 HF BA
                                                                                      • Sleeps 12
                                                                                      11
                                                                                        Exceptional! 5.0/5
                                                                                        (5 reviews)
                                                                                        avg/night
                                                                                        • 3 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 8
                                                                                        5
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                          11
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 5
                                                                                              Wonderful! 4.9/5
                                                                                              (15 reviews)
                                                                                              avg/night
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 6
                                                                                              15
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 6
                                                                                                5
                                                                                                  Excellent! 4.6/5
                                                                                                  (8 reviews)
                                                                                                  avg/night
                                                                                                  • 4 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 9
                                                                                                  8
                                                                                                    • 2 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 5
                                                                                                    21
                                                                                                      • 2 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 6
                                                                                                      • 1 - 50 of 900+
                                                                                                       

                                                                                                      Recent Drakes Island Reviews

                                                                                                      Better than a Hotel!

                                                                                                      5 of 5
                                                                                                      The property was clean and comfortable, with room to move. Would stay here again and would highly recommend it to others!
                                                                                                      • Submitted: Sep 27, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      Cute cottage very clean

                                                                                                      4 of 5
                                                                                                      The property was beautiful. We had a great time the only downfall was it was the end of the season and the landscaping crew was digging up the front path that was my only problem or complaint. We had an amazing time everything was really clean everything we needed was there very accommodating I would definitely rent again from Larry
                                                                                                      • Submitted: Sep 26, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      BEST PLACE IN TOWN!

                                                                                                      5 of 5
                                                                                                      We had a wonderful time at this condo. The description says it all..............it was very clean, it was extremely quaint and cozy, and absolutely the the RETREAT we were looking for. The unit was decorated beautifully and it was very comfortable. We really enjoyed the large outdoor hot tub and heated pool. This condo is the center of everything we wanted to do. Chris suggested Drakes Island Beach for us and it was perfect. It is also a short drive to Kennebunk and Ogunquit. Marginal Way and Perkins Cove are a must. What a beautiful scenic walk along the coast in Ogunquit. We will definitely refer our friends and family. Already looking at our calendar to return next year!
                                                                                                      • Submitted: Sep 25, 2016
                                                                                                      • Stayed: Sep 2016