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Old Town: Houses, Cottages & More (226)

  • 1 - 50 of 226
Additional fees apply. Taxes may be added.
    Wonderful! 4.9/5
    (13 reviews)
    avg/night
    • 3 BR
    • 3 BA
    • 1 HF BA
    • Sleeps 6
    Townhome #637828vb
    13
    Viewed 34 times in the last 48 hours
      Excellent! 4.5/5
      (28 reviews)
      avg/night
      • Studio
      • 1 BA
      • Sleeps 2
      Hotel #3937833
      28
      Viewed 35 times in the last 48 hours
        Excellent! 4.7/5
        (26 reviews)
        avg/night
        • 5 BR
        • 3 BA
        • 1 HF BA
        • Sleeps 16
        House #3650143
        26
        Viewed 45 times in the last 48 hours
          Exceptional! 5.0/5
          (66 reviews)
          avg/night
          • 2 BR
          • 2 BA
          • Sleeps 4
          House #420695vb
          66
          Viewed 44 times in the last 48 hours
            Excellent! 4.5/5
            (62 reviews)
            avg/night
            • Studio
            • 1 BA
            • Sleeps 2
            Condo #3650102
            62
            Viewed 51 times in the last 48 hours
              Wonderful! 4.8/5
              (9 reviews)
              avg/night
              • 1 BR
              • 1 BA
              • Sleeps 3
              House #810549vb
              9
              Viewed 32 times in the last 48 hours
                Wonderful! 4.8/5
                (18 reviews)
                avg/night
                • 3 BR
                • 3 BA
                • Sleeps 8
                House #177596vb
                18
                Viewed 41 times in the last 48 hours
                  Exceptional! 5.0/5
                  (7 reviews)
                  avg/night
                  • 1 BR
                  • 1 BA
                  • Sleeps 4
                  Cottage #481491vb
                  7
                  Viewed 16 times in the last 48 hours
                    Excellent! 4.7/5
                    (37 reviews)
                    avg/night
                    • Studio
                    • 1 BA
                    • Sleeps 2
                    Hotel #3937828
                    37
                    Viewed 52 times in the last 48 hours
                      Excellent! 4.6/5
                      (23 reviews)
                      avg/night
                      • Studio
                      • 1 BA
                      • Sleeps 2
                      Hotel #3937836
                      23
                      Viewed 31 times in the last 48 hours
                        Excellent! 4.5/5
                        (30 reviews)
                        avg/night
                        • Studio
                        • 1 BA
                        • Sleeps 2
                        Hotel #3937830
                        30
                        Viewed 50 times in the last 48 hours
                          Excellent! 4.5/5
                          (35 reviews)
                          avg/night
                          • 2 BR
                          • 2 BA
                          • Sleeps 4
                          House #475033vb
                          35
                          Viewed 18 times in the last 48 hours
                            Wonderful! 4.8/5
                            (51 reviews)
                            avg/night
                            • 1 BR
                            • 1 BA
                            • Sleeps 4
                            Cabin #137869vb
                            51
                            Viewed 7 times in the last 48 hours
                              Excellent! 4.6/5
                              (14 reviews)
                              avg/night
                              • 2 BR
                              • 2 BA
                              • Sleeps 4
                              House #3957926
                              14
                              Viewed 39 times in the last 48 hours
                                Excellent! 4.4/5
                                (17 reviews)
                                avg/night
                                • 2 BR
                                • 2 BA
                                • Sleeps 6
                                Cottage #466459vb
                                17
                                Viewed 18 times in the last 48 hours
                                  Excellent! 4.4/5
                                  (66 reviews)
                                  avg/night
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 4
                                  Condo #3650101
                                  66
                                  Viewed 45 times in the last 48 hours
                                    Very Good! 4.0/5
                                    (29 reviews)
                                    avg/night
                                    • Studio
                                    • 1 BA
                                    • Sleeps 2
                                    Hotel #3937834
                                    29
                                    Viewed 156 times in the last 48 hours
                                      • 5 BR
                                      • 5 BA
                                      • 1 HF BA
                                      • Sleeps 12
                                      House #600556vb
                                      4
                                      Viewed 22 times in the last 48 hours
                                        Excellent! 4.5/5
                                        (21 reviews)
                                        avg/night
                                        • 2 BR
                                        • 1 BA
                                        • Sleeps 6
                                        Cottage #466457vb
                                        21
                                        Viewed 16 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 55 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 9 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
                                                (14 reviews)
                                                avg/night
                                                • 3 BR
                                                • 3 BA
                                                • Sleeps 6
                                                Villa #754594vb
                                                14
                                                Viewed 73 times in the last 48 hours
                                                  avg/night
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 4
                                                  Cottage #4094995
                                                  2 Reviews
                                                  Viewed 30 times in the last 48 hours
                                                    avg/night
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    House #915762vb
                                                    1 Review
                                                    Viewed 45 times in the last 48 hours
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 4
                                                      House #843708vb
                                                      Viewed 7 times in the last 48 hours
                                                        Exceptional! 5.0/5
                                                        (20 reviews)
                                                        avg/night
                                                        • 2 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        Condo #3773904
                                                        20
                                                        Viewed 54 times in the last 48 hours
                                                          Excellent! 4.7/5
                                                          (54 reviews)
                                                          avg/night
                                                          • Studio
                                                          • 1 BA
                                                          • Sleeps 2
                                                          Studio #332511
                                                          54
                                                          Viewed 50 times in the last 48 hours
                                                            Excellent! 4.3/5
                                                            (29 reviews)
                                                            avg/night
                                                            • Studio
                                                            • 1 BA
                                                            • Sleeps 2
                                                            Hotel #3937831
                                                            29
                                                            Viewed 70 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 10 times in the last 48 hours
                                                                • Studio
                                                                • 1 BA
                                                                • Sleeps 2
                                                                Studio #4227875
                                                                Viewed 31 times in the last 48 hours
                                                                  • 9 BR
                                                                  • 9 BA
                                                                  • Sleeps 18
                                                                  Hotel #3940032
                                                                  Viewed 21 times in the last 48 hours
                                                                    Exceptional! 5.0/5
                                                                    (18 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 3 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 8
                                                                    Townhome #3621703
                                                                    18
                                                                    Viewed 17 times in the last 48 hours
                                                                      Excellent! 4.4/5
                                                                      (61 reviews)
                                                                      avg/night
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      Condo #3650166
                                                                      61
                                                                      Viewed 32 times in the last 48 hours
                                                                        Excellent! 4.7/5
                                                                        (13 reviews)
                                                                        avg/night
                                                                        • 2 BR
                                                                        • 2 BA
                                                                        • Sleeps 6
                                                                        Condo #4091151
                                                                        13
                                                                        Viewed 71 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (15 reviews)
                                                                          avg/night
                                                                          • 6 BR
                                                                          • 6 BA
                                                                          • Sleeps 16
                                                                          House #496751vb
                                                                          15
                                                                          Viewed 87 times in the last 48 hours
                                                                            Wonderful! 4.9/5
                                                                            (7 reviews)
                                                                            avg/night
                                                                            • 2 BR
                                                                            • 2 BA
                                                                            • 1 HF BA
                                                                            • Sleeps 6
                                                                            House #251642vb
                                                                            7
                                                                            Viewed 9 times in the last 48 hours
                                                                              Wonderful! 4.9/5
                                                                              (87 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              Condo #154612
                                                                              87
                                                                              Viewed 57 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! 4.4/5
                                                                                  (33 reviews)
                                                                                  avg/night
                                                                                  • Studio
                                                                                  • 1 BA
                                                                                  • Sleeps 2
                                                                                  Hotel #3937837
                                                                                  33
                                                                                  Viewed 105 times in the last 48 hours
                                                                                    Wonderful! 4.8/5
                                                                                    (5 reviews)
                                                                                    avg/night
                                                                                    • 1 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 4
                                                                                    Condo #497650vb
                                                                                    5
                                                                                    Viewed 9 times in the last 48 hours
                                                                                      avg/night
                                                                                      • 4 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 7
                                                                                      House #329361
                                                                                      4
                                                                                      Viewed 11 times in the last 48 hours
                                                                                        Exceptional! 5.0/5
                                                                                        (5 reviews)
                                                                                        avg/night
                                                                                        • 3 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 6
                                                                                        Villa #692758vb
                                                                                        5
                                                                                        Viewed 81 times in the last 48 hours
                                                                                          Excellent! 4.7/5
                                                                                          (10 reviews)
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                          Condo #4091155
                                                                                          10
                                                                                          Viewed 60 times in the last 48 hours
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 6
                                                                                            Condo #4132811
                                                                                            3
                                                                                            Viewed 120 times in the last 48 hours
                                                                                              Wonderful! 4.8/5
                                                                                              (89 reviews)
                                                                                              avg/night
                                                                                              • 2 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 6
                                                                                              House #904144
                                                                                              89
                                                                                              Viewed 59 times in the last 48 hours
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 4
                                                                                                Cottage #4095022
                                                                                                Viewed 9 times in the last 48 hours
                                                                                                  Excellent! 4.7/5
                                                                                                  (32 reviews)
                                                                                                  avg/night
                                                                                                  • Studio
                                                                                                  • 1 BA
                                                                                                  • Sleeps 2
                                                                                                  Hotel #3937829
                                                                                                  32
                                                                                                  Viewed 14 times in the last 48 hours
                                                                                                    Wonderful! 4.8/5
                                                                                                    (6 reviews)
                                                                                                    • 2 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 6
                                                                                                    House #801638vb
                                                                                                    6
                                                                                                    Viewed 21 times in the last 48 hours
                                                                                                    • 1 - 50 of 226
                                                                                                     

                                                                                                    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