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  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
    Wonderful! 4.9/5
    (72 reviews)
    avg/night
    • 1 BR
    • 1 BA
    • Sleeps 2
    Condo #297241vb
    72
    Viewed 290 times in the last 48 hours
      Wonderful! 4.9/5
      (12 reviews)
      avg/night
      • 2 BR
      • 2 BA
      • Sleeps 4
      House #3864846
      12
      Viewed 389 times in the last 48 hours
        Wonderful! 4.9/5
        (88 reviews)
        avg/night
        • 2 BR
        • 1 BA
        • Sleeps 4
        Condo #244472
        88
        Viewed 146 times in the last 48 hours
          Wonderful! 4.9/5
          (65 reviews)
          avg/night
          • 2 BR
          • 1 BA
          • Sleeps 4
          Condo #156723
          65
          Viewed 288 times in the last 48 hours
            Very Good! 4.2/5
            (57 reviews)
            avg/night
            • Studio
            • 1 BA
            • Sleeps 2
            Studio #3656402
            57
            Viewed 443 times in the last 48 hours
              Exceptional! 5.0/5
              (51 reviews)
              avg/night
              • 2 BR
              • 1 BA
              • Sleeps 4
              Condo #938538
              51
              Viewed 77 times in the last 48 hours
                Exceptional! 5.0/5
                (44 reviews)
                avg/night
                • 4 BR
                • 3 BA
                • Sleeps 8
                Townhome #220630
                44
                Viewed 196 times in the last 48 hours
                  Wonderful! 4.9/5
                  (87 reviews)
                  avg/night
                  • 2 BR
                  • 2 BA
                  • Sleeps 6
                  Condo #154612
                  87
                  Viewed 189 times in the last 48 hours
                    Excellent! 4.4/5
                    (49 reviews)
                    avg/night
                    • 3 BR
                    • 2 BA
                    • Sleeps 8
                    Cottage #959155
                    49
                    Viewed 284 times in the last 48 hours
                      Wonderful! 4.9/5
                      (23 reviews)
                      avg/night
                      • 2 BR
                      • 1 BA
                      • Sleeps 4
                      Condo #4018549
                      23
                      Viewed 235 times in the last 48 hours
                        Excellent! 4.7/5
                        (15 reviews)
                        avg/night
                        • 2 BR
                        • 2 BA
                        • Sleeps 6
                        Condo #4091151
                        15
                        Viewed 226 times in the last 48 hours
                          Excellent! 4.6/5
                          (14 reviews)
                          avg/night
                          • 2 BR
                          • 2 BA
                          • Sleeps 6
                          Condo #4091155
                          14
                          Viewed 309 times in the last 48 hours
                            Wonderful! 4.8/5
                            (56 reviews)
                            avg/night
                            • 2 BR
                            • 1 BA
                            • Sleeps 4
                            Condo #261681
                            56
                            Viewed 141 times in the last 48 hours
                              Wonderful! 4.9/5
                              (27 reviews)
                              avg/night
                              • 2 BR
                              • 1 BA
                              • 1 HF BA
                              • Sleeps 5
                              Townhome #3552474
                              27
                              Viewed 155 times in the last 48 hours
                                Exceptional! 5.0/5
                                (30 reviews)
                                avg/night
                                • 3 BR
                                • 2 BA
                                • Sleeps 8
                                House #4095019
                                30
                                Viewed 168 times in the last 48 hours
                                  Wonderful! 4.9/5
                                  (42 reviews)
                                  avg/night
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 2
                                  Condo #934388
                                  42
                                  Viewed 37 times in the last 48 hours
                                    Wonderful! 4.9/5
                                    (30 reviews)
                                    avg/night
                                    • 2 BR
                                    • 2 BA
                                    • Sleeps 4
                                    Townhome #3813999
                                    30
                                    Viewed 97 times in the last 48 hours
                                      Wonderful! 4.8/5
                                      (20 reviews)
                                      avg/night
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 4
                                      Condo #712180vb
                                      20
                                      Viewed 155 times in the last 48 hours
                                        Wonderful! 4.8/5
                                        (20 reviews)
                                        avg/night
                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 6
                                        Cottage #987489
                                        20
                                        Viewed 94 times in the last 48 hours
                                          Excellent! 4.7/5
                                          (58 reviews)
                                          avg/night
                                          • Studio
                                          • 1 BA
                                          • Sleeps 2
                                          Studio #7052275
                                          58
                                          Viewed 232 times in the last 48 hours
                                            Excellent! 4.7/5
                                            (58 reviews)
                                            avg/night
                                            • Studio
                                            • 1 BA
                                            • Sleeps 2
                                            Studio #332511
                                            58
                                            Viewed 66 times in the last 48 hours
                                              Exceptional! 5.0/5
                                              (6 reviews)
                                              avg/night
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 4
                                              Villa #678768vb
                                              6
                                              Viewed 90 times in the last 48 hours
                                                Wonderful! 4.8/5
                                                (18 reviews)
                                                avg/night
                                                • 2 BR
                                                • 1 BA
                                                • 1 HF BA
                                                • Sleeps 5
                                                Condo #3941286
                                                18
                                                Viewed 63 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (61 reviews)
                                                  avg/night
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 4
                                                  Condo #433844vb
                                                  61
                                                  Viewed 103 times in the last 48 hours
                                                    Excellent! 4.7/5
                                                    (24 reviews)
                                                    avg/night
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 5
                                                    Condo #500949vb
                                                    24
                                                    Viewed 59 times in the last 48 hours
                                                      • 2 BR
                                                      • 2 BA
                                                      • 1 HF BA
                                                      • Sleeps 6
                                                      Condo #653503vb
                                                      4
                                                      Viewed 53 times in the last 48 hours
                                                        Wonderful! 4.8/5
                                                        (29 reviews)
                                                        $97
                                                        avg/night
                                                        • 2 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        House #618900vb
                                                        29
                                                        Viewed 141 times in the last 48 hours
                                                          Exceptional! 5.0/5
                                                          (27 reviews)
                                                          avg/night
                                                          • 4 BR
                                                          • 4 BA
                                                          • 1 HF BA
                                                          • Sleeps 10
                                                          House #3848808
                                                          27
                                                          Viewed 109 times in the last 48 hours
                                                            Wonderful! 4.8/5
                                                            (20 reviews)
                                                            avg/night
                                                            • 3 BR
                                                            • 3 BA
                                                            • Sleeps 8
                                                            House #177596vb
                                                            20
                                                            Viewed 209 times in the last 48 hours
                                                              Wonderful! 4.8/5
                                                              (91 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 3 BA
                                                              • Sleeps 6
                                                              House #904144
                                                              91
                                                              Viewed 117 times in the last 48 hours
                                                                Excellent! 4.6/5
                                                                (22 reviews)
                                                                avg/night
                                                                • 2 BR
                                                                • 2 BA
                                                                • 1 HF BA
                                                                • Sleeps 4
                                                                Townhome #148626vb
                                                                22
                                                                Viewed 54 times in the last 48 hours
                                                                  Excellent! 4.5/5
                                                                  (65 reviews)
                                                                  avg/night
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 6
                                                                  Condo #3650155
                                                                  65
                                                                  Viewed 110 times in the last 48 hours
                                                                    Wonderful! 4.8/5
                                                                    (6 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 6
                                                                    Villa #677689vb
                                                                    6
                                                                    Viewed 33 times in the last 48 hours
                                                                      Very Good! 4.0/5
                                                                      (23 reviews)
                                                                      avg/night
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 2
                                                                      Studio #3789148
                                                                      23
                                                                      Viewed 76 times in the last 48 hours
                                                                        Excellent! 4.4/5
                                                                        (5 reviews)
                                                                        avg/night
                                                                        • 2 BR
                                                                        • 2 BA
                                                                        • Sleeps 6
                                                                        Condo #4132811
                                                                        5
                                                                        Viewed 115 times in the last 48 hours
                                                                          Excellent! 4.6/5
                                                                          (19 reviews)
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 6
                                                                          Townhome #3539485
                                                                          19
                                                                          Viewed 68 times in the last 48 hours
                                                                            Wonderful! 4.9/5
                                                                            (12 reviews)
                                                                            avg/night
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 6
                                                                            Condo #466455vb
                                                                            12
                                                                            Viewed 139 times in the last 48 hours
                                                                              Excellent! 4.4/5
                                                                              (62 reviews)
                                                                              avg/night
                                                                              • Studio
                                                                              • 1 BA
                                                                              • Sleeps 2
                                                                              Condo #3650109
                                                                              62
                                                                              Viewed 244 times in the last 48 hours
                                                                                Exceptional! 5.0/5
                                                                                (5 reviews)
                                                                                avg/night
                                                                                • 3 BR
                                                                                • 3 BA
                                                                                • Sleeps 6
                                                                                Villa #692758vb
                                                                                5
                                                                                Viewed 159 times in the last 48 hours
                                                                                  Wonderful! 4.9/5
                                                                                  (16 reviews)
                                                                                  avg/night
                                                                                  • 2 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 4
                                                                                  Condo #620942vb
                                                                                  16
                                                                                  Viewed 109 times in the last 48 hours
                                                                                    Exceptional! 5.0/5
                                                                                    (68 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 4
                                                                                    House #420695vb
                                                                                    68
                                                                                    Viewed 125 times in the last 48 hours
                                                                                      Wonderful! 4.8/5
                                                                                      (28 reviews)
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 6
                                                                                      Condo #3624133
                                                                                      28
                                                                                      Viewed 59 times in the last 48 hours
                                                                                        Excellent! 4.5/5
                                                                                        (66 reviews)
                                                                                        avg/night
                                                                                        • Studio
                                                                                        • 1 BA
                                                                                        • Sleeps 2
                                                                                        Condo #3650102
                                                                                        66
                                                                                        Viewed 100 times in the last 48 hours
                                                                                          Excellent! 4.6/5
                                                                                          (8 reviews)
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 2 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 6
                                                                                          Townhome #695754vb
                                                                                          8
                                                                                          Viewed 87 times in the last 48 hours
                                                                                            avg/night
                                                                                            • Studio
                                                                                            • 1 BA
                                                                                            • Sleeps 2
                                                                                            Studio #4251087
                                                                                            2
                                                                                            Viewed 239 times in the last 48 hours
                                                                                              Very Good! 4.2/5
                                                                                              (5 reviews)
                                                                                              avg/night
                                                                                              • 2 BR
                                                                                              • 2 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 6
                                                                                              House #600101vb
                                                                                              5
                                                                                              Viewed 57 times in the last 48 hours
                                                                                                Exceptional! 5.0/5
                                                                                                (20 reviews)
                                                                                                avg/night
                                                                                                • 2 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 6
                                                                                                Condo #3773904
                                                                                                20
                                                                                                Viewed 75 times in the last 48 hours
                                                                                                  Wonderful! 4.9/5
                                                                                                  (17 reviews)
                                                                                                  avg/night
                                                                                                  • 3 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 6
                                                                                                  Villa #754594vb
                                                                                                  17
                                                                                                  Viewed 55 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (9 reviews)
                                                                                                    avg/night
                                                                                                    • 1 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 4
                                                                                                    Condo #877318vb
                                                                                                    9
                                                                                                    Viewed 203 times in the last 48 hours
                                                                                                      Wonderful! 4.9/5
                                                                                                      (35 reviews)
                                                                                                      avg/night
                                                                                                      • 2 BR
                                                                                                      • 1 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 5
                                                                                                      Villa #390205
                                                                                                      35
                                                                                                      Viewed 21 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Old Town: Houses, Condos & More (300+)

                                                                                                       

                                                                                                      Recent Old Town Reviews

                                                                                                      Wonderful condo, we loved it!

                                                                                                      5 of 5
                                                                                                      This is a lovely condo. We were very impressed with the property and surrounding area. The condo was even nicer in person than the photos for the listing, and was spotless upon arrival. Such a relaxing place to stay in Key West. Unless you are planning on going further up the Keys, you do not need a vehicle if you fly into Key West. Easy cab ride to the condo and bike rentals are the way to go! We would definitely stay here again. The proximity to both Fort Zachary Taylor State Park and Duval Street was a huge bonus. Thank you Alicia for sharing your wonderful home with us! Kelly and Jerry
                                                                                                      • Submitted: Jan 18, 2017
                                                                                                      • Stayed: Jan 2017

                                                                                                      Best place!!

                                                                                                      5 of 5
                                                                                                      We have been renting through VRBO for quite a few years now but this is the first time in Key West. Not only were we impressed with the house for Key West but it was one of the best houses we've rented. Patty was a delight. The house was very pretty and VERY clean. Every detail was addressed. There was a well stocked kitchen so we could enjoy some homemade delights. As far as location goes I don't know if it could get any better. More security than many places and almost everything is within walking distance. We would definitely stay there again!
                                                                                                      • Submitted: Jan 17, 2017
                                                                                                      • Stayed: Jan 2017

                                                                                                      Quiet Oasis

                                                                                                      5 of 5
                                                                                                      Three couples had a great week at the cottage. It is a quiet oasis just a short walk from Duval Street and the Zachary State Park. We enjoyed sitting on the back lower deck for our breakfast each day. The spacious top deck was perfect for watching the cruise ships arrive and depart each day. We will be back!
                                                                                                      • Submitted: Jan 16, 2017
                                                                                                      • Stayed: Jan 2017