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Old Town: Houses, Cottages & More (206)

  • 1 - 50 of 206
Additional fees apply. Taxes may be added.
    Excellent! 4.7/5
    (54 reviews)
    avg/night
    • Studio
    • 1 BA
    • Sleeps 2
    Studio #332511
    54
    Viewed 34 times in the last 48 hours
      Wonderful! 4.8/5
      (18 reviews)
      avg/night
      • 3 BR
      • 3 BA
      • Sleeps 8
      House #177596vb
      18
      Viewed 77 times in the last 48 hours
        Excellent! 4.5/5
        (21 reviews)
        avg/night
        • 2 BR
        • 1 BA
        • Sleeps 6
        Cottage #466457vb
        21
        Viewed 20 times in the last 48 hours
          Wonderful! 4.8/5
          (9 reviews)
          avg/night
          • 1 BR
          • 1 BA
          • Sleeps 3
          House #810549vb
          9
          Viewed 10 times in the last 48 hours
            Excellent! 4.6/5
            (14 reviews)
            avg/night
            • 2 BR
            • 2 BA
            • Sleeps 4
            House #3957926
            14
            Viewed 30 times in the last 48 hours
              Excellent! 4.7/5
              (37 reviews)
              avg/night
              • Studio
              • 1 BA
              • Sleeps 2
              Hotel #3937828
              37
              Viewed 26 times in the last 48 hours
                • Studio
                • 1 BA
                • Sleeps 2
                Studio #4227875
                Viewed 11 times in the last 48 hours
                  avg/night
                  • 3 BR
                  • 2 BA
                  • Sleeps 6
                  House #915762vb
                  1
                  Viewed 33 times in the last 48 hours
                    Excellent! 4.5/5
                    (62 reviews)
                    avg/night
                    • Studio
                    • 1 BA
                    • Sleeps 2
                    Condo #3650102
                    62
                    Viewed 24 times in the last 48 hours
                      Excellent! 4.4/5
                      (17 reviews)
                      avg/night
                      • 2 BR
                      • 2 BA
                      • Sleeps 6
                      Cottage #466459vb
                      17
                      Viewed 16 times in the last 48 hours
                        Excellent! 4.4/5
                        (61 reviews)
                        avg/night
                        • 1 BR
                        • 1 BA
                        • Sleeps 4
                        Condo #3650166
                        61
                        Viewed 17 times in the last 48 hours
                          Excellent! 4.6/5
                          (23 reviews)
                          avg/night
                          • Studio
                          • 1 BA
                          • Sleeps 2
                          Hotel #3937836
                          23
                          Viewed 27 times in the last 48 hours
                            Wonderful! 4.8/5
                            (51 reviews)
                            avg/night
                            • 1 BR
                            • 1 BA
                            • Sleeps 4
                            Cabin #137869vb
                            51
                            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 9 times in the last 48 hours
                                Very Good! 4.0/5
                                (29 reviews)
                                avg/night
                                • Studio
                                • 1 BA
                                • Sleeps 2
                                Hotel #3937834
                                29
                                Viewed 54 times in the last 48 hours
                                  • Studio
                                  • 1 BA
                                  • Sleeps 2
                                  Hotel #3937835
                                  42
                                    Exceptional! 5.0/5
                                    (7 reviews)
                                    avg/night
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 4
                                    Cottage #481491vb
                                    7
                                    Viewed 24 times in the last 48 hours
                                      Excellent! 4.5/5
                                      (30 reviews)
                                      avg/night
                                      • Studio
                                      • 1 BA
                                      • Sleeps 2
                                      Hotel #3937830
                                      30
                                      Viewed 49 times in the last 48 hours
                                        Excellent! 4.3/5
                                        (29 reviews)
                                        avg/night
                                        • Studio
                                        • 1 BA
                                        • Sleeps 2
                                        Hotel #3937831
                                        29
                                        Viewed 31 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
                                            Exceptional! 5.0/5
                                            (5 reviews)
                                            avg/night
                                            • 3 BR
                                            • 3 BA
                                            • Sleeps 6
                                            Villa #692758vb
                                            5
                                            Viewed 42 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 14 times in the last 48 hours
                                                Excellent! 4.4/5
                                                (33 reviews)
                                                avg/night
                                                • Studio
                                                • 1 BA
                                                • Sleeps 2
                                                Hotel #3937837
                                                33
                                                Viewed 39 times in the last 48 hours
                                                  Very Good! 4.1/5
                                                  (7 reviews)
                                                  avg/night
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 3
                                                  House #810548vb
                                                  7
                                                  Viewed 6 times in the last 48 hours
                                                    Exceptional! 5.0/5
                                                    (66 reviews)
                                                    avg/night
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 4
                                                    House #420695vb
                                                    66
                                                    Viewed 13 times in the last 48 hours
                                                      Wonderful! 4.9/5
                                                      (14 reviews)
                                                      avg/night
                                                      • 3 BR
                                                      • 3 BA
                                                      • Sleeps 6
                                                      Villa #754594vb
                                                      14
                                                      Viewed 39 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 39 times in the last 48 hours
                                                          Excellent! 4.3/5
                                                          (67 reviews)
                                                          avg/night
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 4
                                                          Condo #3650100
                                                          67
                                                          Viewed 27 times in the last 48 hours
                                                            Excellent! 4.4/5
                                                            (66 reviews)
                                                            avg/night
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            Condo #3650101
                                                            66
                                                            Viewed 35 times in the last 48 hours
                                                              Exceptional! 5.0/5
                                                              (16 reviews)
                                                              avg/night
                                                              • 3 BR
                                                              • 3 BA
                                                              • 1 HF BA
                                                              • Sleeps 8
                                                              House #652839vb
                                                              16
                                                              Viewed 5 times in the last 48 hours
                                                                Exceptional! 5.0/5
                                                                (20 reviews)
                                                                avg/night
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 6
                                                                Condo #3773904
                                                                20
                                                                Viewed 20 times in the last 48 hours
                                                                  Wonderful! 4.9/5
                                                                  (13 reviews)
                                                                  avg/night
                                                                  • 3 BR
                                                                  • 3 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 6
                                                                  Townhome #637828vb
                                                                  13
                                                                  Viewed 12 times in the last 48 hours
                                                                    Exceptional! 5.0/5
                                                                    (5 reviews)
                                                                    avg/night
                                                                    • 5 BR
                                                                    • 3 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 10
                                                                    House #497773vb
                                                                    5
                                                                    Viewed 96 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (7 reviews)
                                                                      avg/night
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 6
                                                                      Condo #4210064
                                                                      7
                                                                      Viewed 8 times in the last 48 hours
                                                                        • 2 BR
                                                                        • 1 BA
                                                                        • Sleeps 4
                                                                        House #271512vb
                                                                        1
                                                                          Excellent! 4.5/5
                                                                          (35 reviews)
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 4
                                                                          House #475033vb
                                                                          35
                                                                          Viewed 8 times in the last 48 hours
                                                                            Wonderful! 4.8/5
                                                                            (8 reviews)
                                                                            avg/night
                                                                            • Studio
                                                                            • 1 BA
                                                                            • Sleeps 2
                                                                            Cottage #497651vb
                                                                            8
                                                                            Viewed 9 times in the last 48 hours
                                                                              Wonderful! 4.8/5
                                                                              (44 reviews)
                                                                              avg/night
                                                                              • 4 BR
                                                                              • 4 BA
                                                                              • Sleeps 8
                                                                              House #256054vb
                                                                              44
                                                                              Viewed 14 times in the last 48 hours
                                                                                Excellent! 4.5/5
                                                                                (28 reviews)
                                                                                avg/night
                                                                                • Studio
                                                                                • 1 BA
                                                                                • Sleeps 2
                                                                                Hotel #3937833
                                                                                28
                                                                                Viewed 36 times in the last 48 hours
                                                                                  Excellent! 4.7/5
                                                                                  (47 reviews)
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  House #3650175
                                                                                  47
                                                                                  Viewed 7 times in the last 48 hours
                                                                                    avg/night
                                                                                    • Studio
                                                                                    • 1 BA
                                                                                    • Sleeps 2
                                                                                    Apartment #884743vb
                                                                                    Viewed 5 times in the last 48 hours
                                                                                      • 4 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 7
                                                                                      House #329361
                                                                                      4
                                                                                        Wonderful! 4.8/5
                                                                                        (89 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 6
                                                                                        House #904144
                                                                                        89
                                                                                        Viewed 20 times in the last 48 hours
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 6
                                                                                          Apartment #879401vb
                                                                                          Viewed 11 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 43 times in the last 48 hours
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              Cottage #4095022
                                                                                              Viewed 7 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (7 reviews)
                                                                                                avg/night
                                                                                                • 2 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 7
                                                                                                House #390179
                                                                                                7
                                                                                                Viewed 19 times in the last 48 hours
                                                                                                  • 2 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6
                                                                                                  House #801638vb
                                                                                                  6
                                                                                                    Exceptional! 5.0/5
                                                                                                    (11 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 8
                                                                                                    House #3751472
                                                                                                    11
                                                                                                    Viewed 13 times in the last 48 hours
                                                                                                      • 1 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 4
                                                                                                      Apartment #4138312
                                                                                                      2
                                                                                                      Viewed 6 times in the last 48 hours
                                                                                                      • 1 - 50 of 206
                                                                                                       

                                                                                                      Recent Old Town Reviews

                                                                                                      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

                                                                                                      Mixed feelings

                                                                                                      4 of 5
                                                                                                      Rating Details: The property manager was adequately helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Room 6 was fine except for a 1.5" gap netween the air conditioner and window frame where you could see outside and that could let bugs into the room. Not good. I did point it out and hope they fix it. Breakfast during the week is ok. Last time I stayed on the weekend and had a lovely breakfast cooked to order. Had to drive around in the drizzle for a while looking for a parking spot but finally found one about a block-and-a-half away. I asked for a receipt when I checked out but was told they don't give them. Asked if they had any bottled water and was told no. Not overly friendly. So different than my first stay. I would probably look for another place to stay next time I'm in Key West.
                                                                                                      • Submitted: Dec 2, 2016
                                                                                                      • Stayed: Nov 2016