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Old Town: Houses, Cottages & More (225)

  • 1 - 50 of 225
Additional fees apply. Taxes may be added.
    Wonderful! 4.9/5
    (87 reviews)
    avg/night
    • 2 BR
    • 2 BA
    • Sleeps 6
    Condo #154612
    87
    Viewed 71 times in the last 48 hours
      Excellent! 4.7/5
      (13 reviews)
      avg/night
      • 2 BR
      • 2 BA
      • Sleeps 6
      Condo #4091151
      13
      Viewed 62 times in the last 48 hours
        Excellent! 4.7/5
        (10 reviews)
        avg/night
        • 2 BR
        • 2 BA
        • Sleeps 6
        Condo #4091155
        10
        Viewed 70 times in the last 48 hours
          • Studio
          • 1 BA
          • Sleeps 2
          Studio #4227875
          Viewed 34 times in the last 48 hours
            Excellent! 4.7/5
            (54 reviews)
            avg/night
            • Studio
            • 1 BA
            • Sleeps 2
            Studio #332511
            54
            Viewed 29 times in the last 48 hours
              Wonderful! 4.8/5
              (6 reviews)
              • 2 BR
              • 2 BA
              • Sleeps 6
              House #801638vb
              6
              Viewed 23 times in the last 48 hours
                Exceptional! 5.0/5
                (5 reviews)
                avg/night
                • 3 BR
                • 3 BA
                • Sleeps 6
                Villa #692758vb
                5
                Viewed 59 times in the last 48 hours
                  Wonderful! 4.8/5
                  (89 reviews)
                  avg/night
                  • 2 BR
                  • 3 BA
                  • Sleeps 6
                  House #904144
                  89
                  Viewed 39 times in the last 48 hours
                    Exceptional! 5.0/5
                    (20 reviews)
                    avg/night
                    • 2 BR
                    • 2 BA
                    • Sleeps 6
                    Condo #3773904
                    20
                    Viewed 36 times in the last 48 hours
                      Wonderful! 4.8/5
                      (87 reviews)
                      avg/night
                      • 3 BR
                      • 2 BA
                      • 1 HF BA
                      • Sleeps 8
                      House #3650170
                      87
                      Viewed 50 times in the last 48 hours
                        Wonderful! 4.8/5
                        (18 reviews)
                        avg/night
                        • 3 BR
                        • 3 BA
                        • Sleeps 8
                        House #177596vb
                        18
                        Viewed 57 times in the last 48 hours
                          Wonderful! 4.9/5
                          (15 reviews)
                          avg/night
                          • 3 BR
                          • 3 BA
                          • Sleeps 6
                          Villa #754594vb
                          15
                          Viewed 61 times in the last 48 hours
                            Excellent! 4.5/5
                            (62 reviews)
                            avg/night
                            • Studio
                            • 1 BA
                            • Sleeps 2
                            Condo #3650102
                            62
                            Viewed 59 times in the last 48 hours
                              • 2 BR
                              • 2 BA
                              • Sleeps 6
                              Condo #4132811
                              3
                              Viewed 101 times in the last 48 hours
                                • 6 BR
                                • 4 BA
                                • 2 HF BA
                                • Sleeps 14
                                Estate #4203245
                                1
                                Viewed 14 times in the last 48 hours
                                  Excellent! 4.4/5
                                  (61 reviews)
                                  avg/night
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 4
                                  Condo #3650166
                                  61
                                  Viewed 41 times in the last 48 hours
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 4
                                    Cottage #4095022
                                    Viewed 16 times in the last 48 hours
                                      Excellent! 4.4/5
                                      (17 reviews)
                                      avg/night
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 6
                                      Cottage #466459vb
                                      17
                                      Viewed 19 times in the last 48 hours
                                        Exceptional! 5.0/5
                                        (7 reviews)
                                        avg/night
                                        • 2 BR
                                        • 1 BA
                                        • Sleeps 4
                                        House #493451vb
                                        7
                                        Viewed 6 times in the last 48 hours
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 4
                                          House #653132vb
                                          2
                                          Viewed 13 times in the last 48 hours
                                            Wonderful! 4.9/5
                                            (36 reviews)
                                            avg/night
                                            • 5 BR
                                            • 5 BA
                                            • 2 HF BA
                                            • Sleeps 12
                                            House #3934400
                                            36
                                            Viewed 69 times in the last 48 hours
                                              Wonderful! 4.9/5
                                              (15 reviews)
                                              avg/night
                                              • 6 BR
                                              • 6 BA
                                              • Sleeps 16
                                              House #496751vb
                                              15
                                              Viewed 101 times in the last 48 hours
                                                • 5 BR
                                                • 5 BA
                                                • 1 HF BA
                                                • Sleeps 12
                                                House #600556vb
                                                4
                                                Viewed 26 times in the last 48 hours
                                                  Exceptional! 5.0/5
                                                  (66 reviews)
                                                  avg/night
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 4
                                                  House #420695vb
                                                  66
                                                  Viewed 36 times in the last 48 hours
                                                    Excellent! 4.5/5
                                                    (21 reviews)
                                                    avg/night
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 6
                                                    Cottage #466457vb
                                                    21
                                                    Viewed 23 times in the last 48 hours
                                                      Excellent! 4.6/5
                                                      (9 reviews)
                                                      avg/night
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 2
                                                      House #653141vb
                                                      9
                                                      Viewed 17 times in the last 48 hours
                                                        Excellent! 4.3/5
                                                        (67 reviews)
                                                        avg/night
                                                        • 1 BR
                                                        • 1 BA
                                                        • Sleeps 4
                                                        Condo #3650100
                                                        67
                                                        Viewed 28 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (20 reviews)
                                                          avg/night
                                                          • 3 BR
                                                          • 3 BA
                                                          • Sleeps 8
                                                          House #3592461
                                                          20
                                                          Viewed 8 times in the last 48 hours
                                                            Excellent! 4.6/5
                                                            (14 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 4
                                                            House #3957926
                                                            14
                                                            Viewed 36 times in the last 48 hours
                                                              • 3 BR
                                                              • 3 BA
                                                              • Sleeps 6
                                                              House #3650142
                                                              4
                                                              Viewed 9 times in the last 48 hours
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                Apartment #732456vb
                                                                1
                                                                  Excellent! 4.4/5
                                                                  (66 reviews)
                                                                  avg/night
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 4
                                                                  Condo #3650101
                                                                  66
                                                                  Viewed 42 times in the last 48 hours
                                                                    Exceptional! 5.0/5
                                                                    (7 reviews)
                                                                    avg/night
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 4
                                                                    Cottage #3469621
                                                                    7
                                                                    Viewed 11 times in the last 48 hours
                                                                      avg/night
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 6
                                                                      Apartment #762022vb
                                                                      1
                                                                      Viewed 15 times in the last 48 hours
                                                                        Exceptional! 5.0/5
                                                                        (5 reviews)
                                                                        avg/night
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 2
                                                                        Condo #766877vb
                                                                        5
                                                                        Viewed 20 times in the last 48 hours
                                                                          Exceptional! 5.0/5
                                                                          (19 reviews)
                                                                          avg/night
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • 1 HF BA
                                                                          • Sleeps 6
                                                                          House #486741vb
                                                                          19
                                                                          Viewed 28 times in the last 48 hours
                                                                            • 2 BR
                                                                            • 2 BA
                                                                            • Sleeps 4
                                                                            House #843708vb
                                                                            Viewed 13 times in the last 48 hours
                                                                              avg/night
                                                                              • 1 BR
                                                                              • 1 BA
                                                                              • Sleeps 4
                                                                              Cottage #4094995
                                                                              2
                                                                              Viewed 19 times in the last 48 hours
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 4
                                                                                Condo #497650vb
                                                                                5
                                                                                  Wonderful! 4.9/5
                                                                                  (13 reviews)
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 3 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 6
                                                                                  Townhome #637828vb
                                                                                  13
                                                                                  Viewed 24 times in the last 48 hours
                                                                                    Exceptional! 5.0/5
                                                                                    (11 reviews)
                                                                                    avg/night
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 8
                                                                                    House #3751472
                                                                                    11
                                                                                    Viewed 7 times in the last 48 hours
                                                                                      Excellent! 4.5/5
                                                                                      (30 reviews)
                                                                                      avg/night
                                                                                      • Studio
                                                                                      • 1 BA
                                                                                      • Sleeps 2
                                                                                      Hotel #3937830
                                                                                      30
                                                                                      Viewed 47 times in the last 48 hours
                                                                                        Excellent! 4.3/5
                                                                                        (29 reviews)
                                                                                        avg/night
                                                                                        • Studio
                                                                                        • 1 BA
                                                                                        • Sleeps 2
                                                                                        Hotel #3937831
                                                                                        29
                                                                                        Viewed 39 times in the last 48 hours
                                                                                          Excellent! 4.4/5
                                                                                          (33 reviews)
                                                                                          avg/night
                                                                                          • Studio
                                                                                          • 1 BA
                                                                                          • Sleeps 2
                                                                                          Hotel #3937837
                                                                                          33
                                                                                          Viewed 82 times in the last 48 hours
                                                                                            Excellent! 4.7/5
                                                                                            (37 reviews)
                                                                                            avg/night
                                                                                            • Studio
                                                                                            • 1 BA
                                                                                            • Sleeps 2
                                                                                            Hotel #3937828
                                                                                            37
                                                                                            Viewed 34 times in the last 48 hours
                                                                                              Excellent! 4.3/5
                                                                                              (42 reviews)
                                                                                              avg/night
                                                                                              • Studio
                                                                                              • 1 BA
                                                                                              • Sleeps 2
                                                                                              Hotel #3937835
                                                                                              42
                                                                                              Viewed 13 times in the last 48 hours
                                                                                                Excellent! 4.7/5
                                                                                                (6 reviews)
                                                                                                avg/night
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 6
                                                                                                House #390211
                                                                                                6
                                                                                                Viewed 11 times in the last 48 hours
                                                                                                  Very Good! 4.0/5
                                                                                                  (29 reviews)
                                                                                                  avg/night
                                                                                                  • Studio
                                                                                                  • 1 BA
                                                                                                  • Sleeps 2
                                                                                                  Hotel #3937834
                                                                                                  29
                                                                                                  Viewed 135 times in the last 48 hours
                                                                                                    Wonderful! 4.8/5
                                                                                                    (14 reviews)
                                                                                                    avg/night
                                                                                                    • 1 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 2
                                                                                                    Studio #392129
                                                                                                    14
                                                                                                    Viewed 10 times in the last 48 hours
                                                                                                      Excellent! 4.7/5
                                                                                                      (32 reviews)
                                                                                                      avg/night
                                                                                                      • Studio
                                                                                                      • 1 BA
                                                                                                      • Sleeps 2
                                                                                                      Hotel #3937829
                                                                                                      32
                                                                                                      Viewed 11 times in the last 48 hours
                                                                                                      • 1 - 50 of 225
                                                                                                       

                                                                                                      Recent Old Town Reviews

                                                                                                      Excellent Old Town location, very well appointed

                                                                                                      5 of 5
                                                                                                      Exceptional property conveniently located in the heart of Old Town Key West. Walk or bike to almost everything. Close to restaurants, shops and Fausto's grocery (which offers delivery). Easy 5-6 blocks to Duval Street dining and night life. Home location is quiet & secluded. The property is beautiful and very well appointed, with all the necessary kitchen appliances and utensils. The outdoor dining area, which includes a large flat screen TV, is exceptional. The pool area is just right for cooling off in the afternoon or a late night refresher, with enough room to get in some exercise if you're so inclined. The sound of the pool's waterfall feature provides a nice relaxing background for time sunbathing, reading or napping. Bedrooms and baths are equally well appointed with above average linens. If you need anything at all, just reach out to Shel at Last Key Realty. He is helpful with his advice and is super attentive if any issues should arise. His attention to detail and prompt response was truly exceptional, and made our stay all the more enjoyable. If you are looking for an exceptional property in a prime location, this is the one. We plan to be back.
                                                                                                      • Submitted: Dec 9, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      Great Escape!

                                                                                                      5 of 5
                                                                                                      Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Both the house and the rental company were great! The house is in a great location! Close to everything and anything that is a little further away you can take the free rental company provided shuttle! Staff at the rental company were also very friendly and accommodating. If I come back to Key West again I will definitely stay with this company again. Also we had 8 girls staying in the house and fit perfectly - the front door is now frosted so you cannot see in so sleeping on the pull out couch was completely fine and comfortable! :)
                                                                                                      • Submitted: Dec 5, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Very comfortabe and great customer service

                                                                                                      5 of 5
                                                                                                      Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Perfect location to bike anywhere and Jared had the BEST referrals for food and fun things to do!!! Thanks Jared! The property was spotless, did not see one bug and very comfy!! loved the patio and pool. We will be back!
                                                                                                      • Submitted: Dec 3, 2016
                                                                                                      • Stayed: Nov 2016