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Old Town: Houses, Cottages & More (228)

  • 1 - 50 of 228
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 50 times in the last 48 hours
      Excellent! 4.7/5
      (13 reviews)
      avg/night
      • 2 BR
      • 2 BA
      • Sleeps 6
      Condo #4091151
      13
      Viewed 31 times in the last 48 hours
        Excellent! 4.7/5
        (15 reviews)
        avg/night
        • 2 BR
        • 2 BA
        • Sleeps 6
        Condo #4091149
        15
        Viewed 20 times in the last 48 hours
          Excellent! 4.7/5
          (10 reviews)
          avg/night
          • 2 BR
          • 2 BA
          • Sleeps 6
          Condo #4091155
          10
          Viewed 22 times in the last 48 hours
            Wonderful! 4.8/5
            (15 reviews)
            avg/night
            • 2 BR
            • 2 BA
            • Sleeps 6
            Condo #4091146
            15
            Viewed 47 times in the last 48 hours
              • Studio
              • 1 BA
              • Sleeps 2
              Studio #4227875
              Viewed 11 times in the last 48 hours
                Excellent! 4.7/5
                (54 reviews)
                avg/night
                • Studio
                • 1 BA
                • Sleeps 2
                Studio #332511
                54
                Viewed 34 times in the last 48 hours
                  • 2 BR
                  • 2 BA
                  • Sleeps 6
                  House #801638vb
                  6
                    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
                      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
                        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! 4.8/5
                          (87 reviews)
                          avg/night
                          • 3 BR
                          • 2 BA
                          • 1 HF BA
                          • Sleeps 8
                          House #3650170
                          87
                          Viewed 39 times in the last 48 hours
                            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
                              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
                                Excellent! 4.5/5
                                (62 reviews)
                                avg/night
                                • Studio
                                • 1 BA
                                • Sleeps 2
                                Condo #3650102
                                62
                                Viewed 24 times in the last 48 hours
                                  • 2 BR
                                  • 2 BA
                                  • Sleeps 6
                                  Condo #4132811
                                  3
                                  Viewed 76 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
                                      • 6 BR
                                      • 4 BA
                                      • 2 HF BA
                                      • Sleeps 14
                                      Estate #4203245
                                      1 Review
                                      Viewed 7 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
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 4
                                          Cottage #4095022
                                          Viewed 7 times in the last 48 hours
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 4
                                            House #653132vb
                                            2 Reviews
                                            Viewed 6 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
                                                Wonderful! 4.9/5
                                                (15 reviews)
                                                avg/night
                                                • 6 BR
                                                • 6 BA
                                                • Sleeps 16
                                                House #496751vb
                                                15
                                                Viewed 43 times in the last 48 hours
                                                  • 5 BR
                                                  • 5 BA
                                                  • 1 HF BA
                                                  • Sleeps 12
                                                  House #600556vb
                                                  4
                                                  Viewed 13 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
                                                      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
                                                        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 27 times in the last 48 hours
                                                            • 3 BR
                                                            • 3 BA
                                                            • Sleeps 8
                                                            House #3592461
                                                            19
                                                              • 3 BR
                                                              • 3 BA
                                                              • Sleeps 6
                                                              House #3650142
                                                              4
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                Apartment #732456vb
                                                                1 Review
                                                                  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
                                                                    (7 reviews)
                                                                    avg/night
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 4
                                                                    Cottage #3469621
                                                                    7
                                                                    Viewed 5 times in the last 48 hours
                                                                      Exceptional! 5.0/5
                                                                      (7 reviews)
                                                                      avg/night
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      House #493451vb
                                                                      7
                                                                      Viewed 12 times in the last 48 hours
                                                                        • 2 BR
                                                                        • 1 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 6
                                                                        Apartment #762022vb
                                                                        1 Review
                                                                          Exceptional! 5.0/5
                                                                          (5 reviews)
                                                                          avg/night
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 2
                                                                          Condo #766877vb
                                                                          5
                                                                          Viewed 7 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! 4.6/5
                                                                              (14 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 4
                                                                              House #3957926
                                                                              14
                                                                              Viewed 30 times in the last 48 hours
                                                                                avg/night
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 4
                                                                                Cottage #4094995
                                                                                2 Reviews
                                                                                Viewed 14 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
                                                                                    (11 reviews)
                                                                                    avg/night
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 8
                                                                                    House #3751472
                                                                                    11
                                                                                    Viewed 13 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! 4.4/5
                                                                                          (33 reviews)
                                                                                          avg/night
                                                                                          • Studio
                                                                                          • 1 BA
                                                                                          • Sleeps 2
                                                                                          Hotel #3937837
                                                                                          33
                                                                                          Viewed 39 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
                                                                                              Hotel #3937835
                                                                                              42
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 6
                                                                                                House #390211
                                                                                                6
                                                                                                  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
                                                                                                    • 3 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 6
                                                                                                    House #4153241
                                                                                                    2 Reviews
                                                                                                      Wonderful! 4.8/5
                                                                                                      (14 reviews)
                                                                                                      avg/night
                                                                                                      • 1 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 2
                                                                                                      Studio #392129
                                                                                                      14
                                                                                                      • 1 - 50 of 228
                                                                                                       

                                                                                                      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