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Surfside: Houses, Cottages & More (300+)

  • 1 - 50 of 300+
Additional fees apply. Taxes may be added.
    Exceptional! 5.0/5
    (8 reviews)
    avg/night
    • 2 BR
    • Sleeps 4
    Cottage #236786
    8
      • 1 BR
      • 1 BA
      • Sleeps 2
      Apartment #883995vb
      4
        Wonderful! 4.8/5
        (13 reviews)
        avg/night
        • 2 BR
        • 1 BA
        • Sleeps 4
        House #396562
        13
        Viewed 24 times in the last 48 hours
          • 4 BR
          • 2 BA
          • 1 HF BA
          • Sleeps 12
          House #364260
          Viewed 7 times in the last 48 hours
            • 4 BR
            • 3 BA
            • Sleeps 8
            House #264885vb
            6
              Exceptional! 5.0/5
              (12 reviews)
              avg/night
              • 3 BR
              • 2 BA
              • Sleeps 6
              Cottage #218173vb
              12
              Viewed 6 times in the last 48 hours
                • 7 BR
                • 5 BA
                • Sleeps 14
                Estate #190830vb
                7
                  Wonderful! 4.8/5
                  (6 reviews)
                  avg/night
                  • 6 BR
                  • 3 BA
                  • Sleeps 14
                  House #3550391
                  6
                    avg/night
                    • 4 BR
                    • 2 BA
                    • 1 HF BA
                    • Sleeps 8
                    House #273865
                    4
                    Viewed 9 times in the last 48 hours
                      Excellent! 4.6/5
                      (10 reviews)
                      avg/night
                      • 3 BR
                      • 2 BA
                      • Sleeps 8
                      House #375608
                      10
                      Viewed 15 times in the last 48 hours
                        avg/night
                        • 4 BR
                        • 3 BA
                        • 1 HF BA
                        • Sleeps 8
                        House #4222866
                        1 Review
                        Viewed 5 times in the last 48 hours
                          Excellent! 4.5/5
                          (11 reviews)
                          avg/night
                          • 3 BR
                          • 2 BA
                          • Sleeps 8
                          House #163840
                          11
                          Viewed 21 times in the last 48 hours
                            avg/night
                            • 6 BR
                            • 6 BA
                            • 3 HF BA
                            • Sleeps 12
                            House #817257vb
                            1 Review
                            Viewed 9 times in the last 48 hours
                              avg/night
                              • 5 BR
                              • 4 BA
                              • 2 HF BA
                              • Sleeps 10
                              House #137085
                              2 Reviews
                              Viewed 6 times in the last 48 hours
                                • 6 BR
                                • 7 BA
                                • 1 HF BA
                                • Sleeps 10
                                Estate #122285
                                3
                                  Exceptional! 5.0/5
                                  (9 reviews)
                                  avg/night
                                  • 4 BR
                                  • 2 BA
                                  • 1 HF BA
                                  • Sleeps 8
                                  House #969974
                                  9
                                  Viewed 12 times in the last 48 hours
                                    • 5 BR
                                    • 4 BA
                                    • 2 HF BA
                                    • Sleeps 14
                                    House #825960vb
                                    2 Reviews
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 6
                                      Cottage #106228
                                      1 Review
                                      Viewed 5 times in the last 48 hours
                                        Excellent! 4.5/5
                                        (8 reviews)
                                        avg/night
                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 8
                                        Townhome #149102
                                        8
                                        Viewed 6 times in the last 48 hours
                                          Wonderful! 4.9/5
                                          (10 reviews)
                                          avg/night
                                          • 6 BR
                                          • 3 BA
                                          • Sleeps 12
                                          House #115275
                                          10
                                          Viewed 10 times in the last 48 hours
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 6
                                            House #989859
                                            12
                                              • 3 BR
                                              • 4 BA
                                              • Sleeps 6
                                              House #393054
                                              11
                                                • 5 BR
                                                • 4 BA
                                                • Sleeps 10
                                                House #371185vb
                                                  Exceptional! 5.0/5
                                                  (6 reviews)
                                                  avg/night
                                                  • 3 BR
                                                  • 2 BA
                                                  • 1 HF BA
                                                  • Sleeps 8
                                                  House #127295vb
                                                  6
                                                  Viewed 6 times in the last 48 hours
                                                    • 4 BR
                                                    • 3 BA
                                                    • 1 HF BA
                                                    • Sleeps 8
                                                    House #179367
                                                    1 Review
                                                      • 4 BR
                                                      • 3 BA
                                                      • 1 HF BA
                                                      • Sleeps 8
                                                      House #708862vb
                                                      3
                                                      Viewed 9 times in the last 48 hours
                                                        Exceptional! 5.0/5
                                                        (9 reviews)
                                                        avg/night
                                                        • 4 BR
                                                        • 3 BA
                                                        • Sleeps 10
                                                        House #308525vb
                                                        9
                                                        Viewed 9 times in the last 48 hours
                                                          • 6 BR
                                                          • 4 BA
                                                          • 1 HF BA
                                                          • Sleeps 12
                                                          House #454433vb
                                                          1 Review
                                                            avg/night
                                                            • 3 BR
                                                            • 1 BA
                                                            • Sleeps 10
                                                            House #803336vb
                                                            2 Reviews
                                                            Viewed 12 times in the last 48 hours
                                                              Exceptional! 5.0/5
                                                              (10 reviews)
                                                              avg/night
                                                              • 3 BR
                                                              • 3 BA
                                                              • Sleeps 8
                                                              Cottage #513391vb
                                                              10
                                                                Wonderful! 4.9/5
                                                                (9 reviews)
                                                                avg/night
                                                                • 3 BR
                                                                • 3 BA
                                                                • 1 HF BA
                                                                • Sleeps 6
                                                                House #641674vb
                                                                9
                                                                  • 5 BR
                                                                  • 5 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 12
                                                                  House #457291vb
                                                                    • 2 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    House #734152vb
                                                                    1 Review
                                                                      • 4 BR
                                                                      • 4 BA
                                                                      • Sleeps 8
                                                                      House #478829vb
                                                                      1 Review
                                                                        • 4 BR
                                                                        • 2 BA
                                                                        • Sleeps 7
                                                                        Cottage #725037vb
                                                                        3
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                          House #109585
                                                                            • 5 BR
                                                                            • 3 BA
                                                                            • 1 HF BA
                                                                            • Sleeps 8
                                                                            House #339343vb
                                                                              • 4 BR
                                                                              • 4 BA
                                                                              • Sleeps 8
                                                                              House #479672vb
                                                                                • 4 BR
                                                                                • 3 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 8
                                                                                House #132673vb
                                                                                13
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 8
                                                                                  House #106233
                                                                                  3
                                                                                    Exceptional! 5.0/5
                                                                                    (9 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 4
                                                                                    Condo #579996vb
                                                                                    9
                                                                                    Viewed 11 times in the last 48 hours
                                                                                      Wonderful! 4.9/5
                                                                                      (11 reviews)
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • 1 HF BA
                                                                                      • Sleeps 6
                                                                                      House #456935vb
                                                                                      11
                                                                                      Viewed 27 times in the last 48 hours
                                                                                        Exceptional! 5.0/5
                                                                                        (5 reviews)
                                                                                        avg/night
                                                                                        • 4 BR
                                                                                        • 2 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 10
                                                                                        House #502234vb
                                                                                        5
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          House #907303vb
                                                                                          3
                                                                                            • 6 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 12
                                                                                            House #153860vb
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 6
                                                                                              House #902528vb
                                                                                              1 Review
                                                                                                Wonderful! 4.9/5
                                                                                                (10 reviews)
                                                                                                avg/night
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 8
                                                                                                Cottage #111120
                                                                                                10
                                                                                                Viewed 8 times in the last 48 hours
                                                                                                  Excellent! 4.7/5
                                                                                                  (11 reviews)
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  Cottage #783338vb
                                                                                                  11
                                                                                                  Viewed 6 times in the last 48 hours
                                                                                                    • 4 BR
                                                                                                    • 4 BA
                                                                                                    • 2 HF BA
                                                                                                    • Sleeps 8
                                                                                                    House #4228999
                                                                                                    1 Review
                                                                                                      Wonderful! 4.9/5
                                                                                                      (14 reviews)
                                                                                                      avg/night
                                                                                                      • 2 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 6
                                                                                                      House #809675vb
                                                                                                      14
                                                                                                      Viewed 29 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Surfside Reviews

                                                                                                      Great Christmas Stroll!

                                                                                                      5 of 5
                                                                                                      We had a wonderful time in Nantucket for the annual Christmas Stroll. Casabella was adorable--well appointed, nicely decorated, clean, and felt much bigger than its listed square footage. Because of its location outside of town we were able to discover a new restaurant (the Sea Grille, highly recommend!) and see a different part of the island. Be aware that if you do not have a car, it is about a 30 minute walk from the Steamship Authority ferry and about a 20-25 min walk to town. However, it's an easy walk with lots of beautiful houses along the way. We were very comfortable and pleased with this great property. We plan to return!
                                                                                                      • Submitted: Dec 6, 2016
                                                                                                      • Stayed: Dec 2016

                                                                                                      Excellent stay

                                                                                                      5 of 5
                                                                                                      House warm, cozy, clean! Close to town, and just perfect for a family to enjoy, lots of privacy !
                                                                                                      • Submitted: Dec 5, 2016
                                                                                                      • Stayed: Dec 2016

                                                                                                      This is our favorite rental!

                                                                                                      5 of 5
                                                                                                      Our family has vacationed on Nantucket many times, and this year's rental is definitely our favorite. We loved eating our meals on the large oceanfront deck, enjoying the ocean views, and having direct access to the beach from our own beach path. The house has the charm of a Victorian cottage plus all of the modern conveniences and supplies that we needed for a great vacation. The owner was was available and helpful when needed, and the cottage was clean and well cared-for. Also, it is so close to the Surfside bike path and bus route that we won't bring our car next year.
                                                                                                      • Submitted: Nov 29, 2016
                                                                                                      • Stayed: Jul 2016