check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag
Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!
  • Showing 1-50 of 115
Additional fees apply. Taxes may be added.
    Wonderful! 4.9/5
    (63 reviews)
    avg/night
    • 2 BR
    • 1 BA
    • Sleeps 4
    Condo #156723
    63
    Viewed 75 times in the last 48 hours
      Excellent! 4.4/5
      (48 reviews)
      avg/night
      • 3 BR
      • 2 BA
      • Sleeps 8
      Cottage #959155
      48
      Viewed 85 times in the last 48 hours
        Exceptional! 5.0/5
        (24 reviews)
        avg/night
        • 3 BR
        • 2 BA
        • Sleeps 8
        House #4095019
        24
        Viewed 61 times in the last 48 hours
          Excellent! 4.7/5
          (54 reviews)
          avg/night
          • Studio
          • 1 BA
          • Sleeps 2
          Studio #7052275
          54
          Viewed 80 times in the last 48 hours
            Excellent! 4.7/5
            (54 reviews)
            avg/night
            • Studio
            • 1 BA
            • Sleeps 2
            Studio #332511
            54
            Viewed 54 times in the last 48 hours
              Excellent! 4.7/5
              (24 reviews)
              avg/night
              • 2 BR
              • 1 BA
              • Sleeps 5
              Condo #500949vb
              24
              Viewed 21 times in the last 48 hours
                Exceptional! 5.0/5
                (25 reviews)
                avg/night
                • 4 BR
                • 4 BA
                • 1 HF BA
                • Sleeps 10
                House #3848808
                25
                Viewed 55 times in the last 48 hours
                  Wonderful! 4.8/5
                  (86 reviews)
                  avg/night
                  • 3 BR
                  • 2 BA
                  • 1 HF BA
                  • Sleeps 8
                  House #3650170
                  86
                  Viewed 90 times in the last 48 hours
                    • 2 BR
                    • 2 BA
                    • Sleeps 6
                    Condo #4132811
                    3
                    Viewed 79 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 6 times in the last 48 hours
                        Very Good! 4.0/5
                        (54 reviews)
                        avg/night
                        • 2 BR
                        • 1 BA
                        • Sleeps 4
                        Cottage #3785479
                        54
                        Viewed 24 times in the last 48 hours
                          Wonderful! 4.9/5
                          (8 reviews)
                          avg/night
                          • Studio
                          • 1 BA
                          • Sleeps 2
                          Studio #816858vb
                          8
                          Viewed 12 times in the last 48 hours
                            Wonderful! 4.9/5
                            (15 reviews)
                            avg/night
                            • 6 BR
                            • 6 BA
                            • Sleeps 16
                            House #496751vb
                            15
                            Viewed 73 times in the last 48 hours
                              Wonderful! 4.8/5
                              (50 reviews)
                              avg/night
                              • 1 BR
                              • 1 BA
                              • 1 HF BA
                              • Sleeps 4
                              Townhome #3650164
                              50
                              Viewed 27 times in the last 48 hours
                                Excellent! 4.6/5
                                (7 reviews)
                                avg/night
                                • 3 BR
                                • 2 BA
                                • Sleeps 8
                                House #497655vb
                                7
                                Viewed 36 times in the last 48 hours
                                  Wonderful! 4.9/5
                                  (10 reviews)
                                  avg/night
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 3
                                  House #643001vb
                                  10
                                  Viewed 9 times in the last 48 hours
                                    Exceptional! 5.0/5
                                    (7 reviews)
                                    avg/night
                                    • 3 BR
                                    • 3 BA
                                    • Sleeps 8
                                    House #3886417
                                    7
                                    Viewed 5 times in the last 48 hours
                                      Exceptional! 5.0/5
                                      (11 reviews)
                                      avg/night
                                      • 3 BR
                                      • 3 BA
                                      • Sleeps 6
                                      House #500804vb
                                      11
                                      Viewed 15 times in the last 48 hours
                                        avg/night
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 4
                                        Cottage #4094995
                                        2
                                        Viewed 34 times in the last 48 hours
                                          Excellent! 4.7/5
                                          (23 reviews)
                                          avg/night
                                          • 3 BR
                                          • 4 BA
                                          • Sleeps 10
                                          House #454169vb
                                          23
                                          Viewed 5 times in the last 48 hours
                                            Wonderful! 4.9/5
                                            (8 reviews)
                                            avg/night
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 5
                                            House #643264vb
                                            8
                                            Viewed 19 times in the last 48 hours
                                              Wonderful! 4.8/5
                                              (9 reviews)
                                              avg/night
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 2
                                              House #3957923
                                              9
                                              Viewed 30 times in the last 48 hours
                                                Excellent! 4.3/5
                                                (31 reviews)
                                                avg/night
                                                • Studio
                                                • 1 BA
                                                • Sleeps 2
                                                Cottage #3782468
                                                31
                                                Viewed 44 times in the last 48 hours
                                                  Excellent! 4.6/5
                                                  (9 reviews)
                                                  avg/night
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 3
                                                  House #643000vb
                                                  9
                                                  Viewed 24 times in the last 48 hours
                                                    Excellent! 4.4/5
                                                    (59 reviews)
                                                    avg/night
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 6
                                                    House #3650154
                                                    59
                                                    Viewed 25 times in the last 48 hours
                                                      Excellent! 4.6/5
                                                      (9 reviews)
                                                      avg/night
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 4
                                                      Condo #496753vb
                                                      9
                                                      Viewed 19 times in the last 48 hours
                                                        Excellent! 4.3/5
                                                        (59 reviews)
                                                        avg/night
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 8
                                                        House #3650176
                                                        59
                                                        Viewed 39 times in the last 48 hours
                                                          Wonderful! 4.8/5
                                                          (8 reviews)
                                                          avg/night
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 4
                                                          House #3957925
                                                          8
                                                          Viewed 50 times in the last 48 hours
                                                            Excellent! 4.6/5
                                                            (53 reviews)
                                                            avg/night
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            Townhome #3650150
                                                            53
                                                            Viewed 10 times in the last 48 hours
                                                              Good! 3.8/5
                                                              (6 reviews)
                                                              avg/night
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 8
                                                              House #3996685
                                                              6
                                                              Viewed 22 times in the last 48 hours
                                                                Excellent! 4.6/5
                                                                (60 reviews)
                                                                avg/night
                                                                • 1 BR
                                                                • 1 BA
                                                                • 1 HF BA
                                                                • Sleeps 4
                                                                Townhome #3650107
                                                                60
                                                                Viewed 29 times in the last 48 hours
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 6
                                                                  House #3650180
                                                                  36
                                                                    Excellent! 4.4/5
                                                                    (45 reviews)
                                                                    avg/night
                                                                    • Studio
                                                                    • 1 BA
                                                                    • Sleeps 2
                                                                    Condo #3650098
                                                                    45
                                                                    Viewed 25 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (90 reviews)
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 3 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 8
                                                                      Townhome #3650149
                                                                      90
                                                                      Viewed 42 times in the last 48 hours
                                                                        Wonderful! 4.8/5
                                                                        (18 reviews)
                                                                        avg/night
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 4
                                                                        Apartment #710218vb
                                                                        18
                                                                        Viewed 36 times in the last 48 hours
                                                                          Excellent! 4.5/5
                                                                          (59 reviews)
                                                                          avg/night
                                                                          • 1 BR
                                                                          • 2 BA
                                                                          • Sleeps 4
                                                                          Condo #3650161
                                                                          59
                                                                          Viewed 40 times in the last 48 hours
                                                                            Excellent! 4.3/5
                                                                            (35 reviews)
                                                                            avg/night
                                                                            • Studio
                                                                            • 1 BA
                                                                            • Sleeps 4
                                                                            Cottage #3782469
                                                                            35
                                                                            Viewed 22 times in the last 48 hours
                                                                              Excellent! 4.6/5
                                                                              (31 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Sleeps 6
                                                                              House #3650094
                                                                              31
                                                                              Viewed 27 times in the last 48 hours
                                                                                Excellent! 4.7/5
                                                                                (62 reviews)
                                                                                avg/night
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 4
                                                                                Townhome #3650108
                                                                                62
                                                                                Viewed 43 times in the last 48 hours
                                                                                  avg/night
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                  Condo #496756vb
                                                                                  3
                                                                                  Viewed 11 times in the last 48 hours
                                                                                    Very Good! 4.1/5
                                                                                    (45 reviews)
                                                                                    avg/night
                                                                                    • Studio
                                                                                    • 1 BA
                                                                                    • Sleeps 2
                                                                                    Condo #3650096
                                                                                    45
                                                                                    Viewed 54 times in the last 48 hours
                                                                                      Excellent! 4.6/5
                                                                                      (33 reviews)
                                                                                      avg/night
                                                                                      • 4 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 12
                                                                                      House #3650111
                                                                                      33
                                                                                      Viewed 33 times in the last 48 hours
                                                                                        Excellent! 4.7/5
                                                                                        (37 reviews)
                                                                                        avg/night
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                        House #3782467
                                                                                        37
                                                                                        Viewed 49 times in the last 48 hours
                                                                                          Excellent! 4.7/5
                                                                                          (6 reviews)
                                                                                          avg/night
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          Condo #496754vb
                                                                                          6
                                                                                            Excellent! 4.4/5
                                                                                            (17 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 6
                                                                                            House #3650112
                                                                                            17
                                                                                            Viewed 29 times in the last 48 hours
                                                                                              Excellent! 4.3/5
                                                                                              (15 reviews)
                                                                                              avg/night
                                                                                              • 5 BR
                                                                                              • 4 BA
                                                                                              • Sleeps 14
                                                                                              House #3782466
                                                                                              15
                                                                                              Viewed 49 times in the last 48 hours
                                                                                                Excellent! 4.4/5
                                                                                                (46 reviews)
                                                                                                avg/night
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 10
                                                                                                House #3650178
                                                                                                46
                                                                                                Viewed 61 times in the last 48 hours
                                                                                                  Wonderful! 4.8/5
                                                                                                  (12 reviews)
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  House #643267vb
                                                                                                  12
                                                                                                  Viewed 62 times in the last 48 hours
                                                                                                    Very Good! 4.1/5
                                                                                                    (32 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • 1 HF BA
                                                                                                    • Sleeps 8
                                                                                                    House #3650095
                                                                                                    32
                                                                                                    Viewed 20 times in the last 48 hours
                                                                                                      Excellent! 4.6/5
                                                                                                      (52 reviews)
                                                                                                      avg/night
                                                                                                      • 1 BR
                                                                                                      • 1 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 4
                                                                                                      Townhome #3650163
                                                                                                      52
                                                                                                      Viewed 9 times in the last 48 hours
                                                                                                      • 1 - 50 of 115

                                                                                                      Downtown: Houses, Cottages & More (115)

                                                                                                       

                                                                                                      Recent Downtown Reviews

                                                                                                      Perfect House in the Perfect Location

                                                                                                      5 of 5
                                                                                                      My husband and I planned a trip to Key West for a birthday celebration and invited three other couples to join us. We needed a place that had four bedrooms and bathrooms so each couple could have their own space and Americana Tropicale gave us that option. When we arrived, we were so pleased to find that the house is even better than described and exceptionally clean. (The photos are good but the house is even nicer than what you see.) It is a gorgeous home in the best location possible for travelers who want to spend itme exploring Key West but also want some peace and quiet. The secluded location was fabulous because even though it is just seconds away from Duval Street (the quieter end) you would never know it. We were able to walk with ease to great restaurants, bars, shops, Mallory Square and other attractions. There is just the right amount of sun in the afternoon for lounging on the patio or relaxing in the pool. We were also incredibly pleased with the management company and received an amazing level of attention and service from our concierge. We would absolutely rent this house again for all these reasons and more, and we can wholeheartedly recommend it for anyone considering a first or return trip to Key West.
                                                                                                      • Submitted: Dec 2, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Chinn Family Thanksgiving

                                                                                                      5 of 5
                                                                                                      Rating Details: The property manager was very helpful. The vacation rental was very clean. 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: All good - great facility and a great time had by all
                                                                                                      • Submitted: Dec 1, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Hemingway's View

                                                                                                      4 of 5
                                                                                                      Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Lovely little home right off Duval.
                                                                                                      • Submitted: Nov 30, 2016
                                                                                                      • Stayed: Nov 2016