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Old Town: Houses, Condos & More (733)

  • 1 - 50 of 733
Additional fees apply. Taxes may be added.
    • 2 BR
    • 1 BA
    • Sleeps 6
    19
      • 2 BR
      • 2 BA
      • Sleeps 6
      8
        • 2 BR
        • 2 BA
        • Sleeps 6
        10
          • 2 BR
          • 2 BA
          • Sleeps 6
          82
            • Studio
            • 1 BA
            • Sleeps 2
            30
              • Studio
              • 1 BA
              • Sleeps 2
              59
                • 1 BR
                • 1 BA
                • Sleeps 4
                5
                  • 2 BR
                  • 2 BA
                  • Sleeps 6
                  15
                    • 2 BR
                    • 2 BA
                    • Sleeps 4
                    12
                      • 1 BR
                      • 1 BA
                      • Sleeps 4
                      61
                        • 1 BR
                        • 1 BA
                        • Sleeps 2
                        7
                          • 2 BR
                          • 2 BA
                          • Sleeps 6
                          11
                            • 2 BR
                            • 2 BA
                            • Sleeps 6
                            62
                              • 2 BR
                              • 2 BA
                              • Sleeps 6
                              10
                                • 1 BR
                                • 1 BA
                                • Sleeps 4
                                55
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 4
                                  51
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 4
                                    66
                                      • Studio
                                      • 1 BA
                                      • Sleeps 2
                                        • Studio
                                        • 1 BA
                                        • Sleeps 2
                                        30
                                          • Studio
                                          • 1 BA
                                          • Sleeps 2
                                          20
                                            • Studio
                                            • 1 BA
                                            • Sleeps 2
                                            27
                                              • Studio
                                              • 1 BA
                                              • Sleeps 2
                                              29
                                                • 3 BR
                                                • 2 BA
                                                • 1 HF BA
                                                • Sleeps 8
                                                80
                                                  • 3 BR
                                                  • 3 BA
                                                  • 1 HF BA
                                                  • Sleeps 8
                                                  15
                                                    • 3 BR
                                                    • 3 BA
                                                    • Sleeps 8
                                                    14
                                                      • 2 BR
                                                      • 2 BA
                                                      • 1 HF BA
                                                      • Sleeps 6
                                                      58
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 4
                                                        7
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 2
                                                          9
                                                            • 3 BR
                                                            • 3 BA
                                                            • Sleeps 6
                                                            14
                                                              • Studio
                                                              • 1 BA
                                                              • Sleeps 2
                                                              36
                                                                • 3 BR
                                                                • 3 BA
                                                                • 1 HF BA
                                                                • Sleeps 6
                                                                12
                                                                  • 3 BR
                                                                  • 3 BA
                                                                  • Sleeps 6
                                                                  5
                                                                    • Studio
                                                                    • 1 BA
                                                                    • Sleeps 2
                                                                    24
                                                                      • Studio
                                                                      • 1 BA
                                                                      • Sleeps 2
                                                                      25
                                                                        • 2 BR
                                                                        • 2 BA
                                                                        • Sleeps 4
                                                                        65
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 6
                                                                          29
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 8
                                                                            20
                                                                              • Studio
                                                                              • 1 BA
                                                                              • Sleeps 2
                                                                              28
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 6
                                                                                45
                                                                                  • 2 BR
                                                                                  • 3 BA
                                                                                  • Sleeps 6
                                                                                  88
                                                                                    • 1 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 4
                                                                                    1 Review
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 8
                                                                                      6
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                        2 Reviews
                                                                                          • 5 BR
                                                                                          • 5 BA
                                                                                          • 2 HF BA
                                                                                          • Sleeps 12
                                                                                          35
                                                                                            • 5 BR
                                                                                            • 3 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 16
                                                                                            26
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 6
                                                                                                  • 2 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6
                                                                                                  6
                                                                                                    • 6 BR
                                                                                                    • 6 BA
                                                                                                    • Sleeps 16
                                                                                                    11
                                                                                                      • 1 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 4
                                                                                                      7
                                                                                                      • 1 - 50 of 733
                                                                                                       

                                                                                                      Recent Old Town Reviews

                                                                                                      50th birthday celebrations

                                                                                                      5 of 5
                                                                                                      We came to Key West to celebrate 2 people turning 50, my sister and aunt. This place was just as fabulous as the description it gives! Beautiful home with a fabulous private pool. There were 6 of us staying and there was plenty of space. Great amenities too. Nice having a washer/dryer and full kitchen. The location is PERFECT, step out of the back door and walk everywhere. We found a wonderful little breakfast gem, Havana's. Absolutely the BEST cheesesteak ever!! Shel was wonderful. So accommodating and extremely nice. This was a perfect way to celebrate a milestone!! We will definitely rent this house again!
                                                                                                      • Submitted: Sep 29, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      Great, cosy, little B&B style place

                                                                                                      4 of 5
                                                                                                      Rating Details: The property manager was more than 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: Curry House was adament in keeping me up to date on my stay prior to my arrival. Although check-in was only possible starting from 3PM, when I arrived around 3:30PM I apparently had received an e-mail letting me know I was late. Chuck, the concierge that day made me feel straight at home and gave me helpful pointers on where to park (watch out for the residential only parking spots, do NOT park there unless you want to pay heavy fines!). Breakfast was good, the room was cosy, cool and clean. The backyard was a lot smaller than the picture shows but there is enough to do on the island not to be forced to stay indoors too much. I definitely recommend it for a calm, pleasant stay at Key West!
                                                                                                      • Submitted: Sep 28, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      BD Party

                                                                                                      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: Very clean and comfortable.
                                                                                                      • Submitted: Sep 26, 2016
                                                                                                      • Stayed: Sep 2016