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Upper Florida Keys: House Rentals (522)

  • 1 - 50 of 300+
Additional fees apply. Taxes may be added.
    Excellent! 4.3/5
    (11 reviews)
    avg/night
    • 2 BR
    • 2 BA
    • Sleeps 6
    House #7093005
    11
    Viewed 35 times in the last 48 hours
      Wonderful! 4.8/5
      (32 reviews)
      avg/night
      • 2 BR
      • 2 BA
      • 1 HF BA
      • Sleeps 4
      House #513264vb
      32
      Viewed 52 times in the last 48 hours
        Wonderful! 4.8/5
        (5 reviews)
        avg/night
        • 2 BR
        • 2 BA
        • 1 HF BA
        • Sleeps 6
        House #4208345
        5
        Viewed 43 times in the last 48 hours
          Wonderful! 4.9/5
          (13 reviews)
          avg/night
          • 2 BR
          • 1 BA
          • Sleeps 4
          House #34491vb
          13
          Viewed 79 times in the last 48 hours
            Wonderful! 4.9/5
            (48 reviews)
            avg/night
            • 2 BR
            • 2 BA
            • 1 HF BA
            • Sleeps 6
            House #326184
            48
            Viewed 60 times in the last 48 hours
              Wonderful! 4.9/5
              (13 reviews)
              avg/night
              • 3 BR
              • 2 BA
              • Sleeps 8
              House #795450vb
              13
              Viewed 63 times in the last 48 hours
                Wonderful! 4.9/5
                (28 reviews)
                avg/night
                • 2 BR
                • 2 BA
                • Sleeps 6
                House #450073vb
                28
                Viewed 43 times in the last 48 hours
                  Wonderful! 4.9/5
                  (20 reviews)
                  avg/night
                  • 2 BR
                  • 2 BA
                  • 1 HF BA
                  • Sleeps 6
                  House #3788659
                  20
                  Viewed 56 times in the last 48 hours
                    Exceptional! 5.0/5
                    (10 reviews)
                    avg/night
                    • 4 BR
                    • 4 BA
                    • Sleeps 10
                    House #816307vb
                    10
                    Viewed 57 times in the last 48 hours
                      Wonderful! 4.9/5
                      (14 reviews)
                      avg/night
                      • 3 BR
                      • 3 BA
                      • Sleeps 6
                      House #24330vb
                      14
                      Viewed 44 times in the last 48 hours
                        • 2 BR
                        • 2 BA
                        • Sleeps 4
                        House #884970vb
                        Viewed 57 times in the last 48 hours
                          Exceptional! 5.0/5
                          (15 reviews)
                          avg/night
                          • 2 BR
                          • 2 BA
                          • 1 HF BA
                          • Sleeps 5
                          House #677953vb
                          15
                          Viewed 28 times in the last 48 hours
                            Excellent! 4.7/5
                            (21 reviews)
                            avg/night
                            • 3 BR
                            • 2 BA
                            • Sleeps 8
                            House #319034vb
                            21
                            Viewed 58 times in the last 48 hours
                              Very Good! 4.2/5
                              (6 reviews)
                              avg/night
                              • 4 BR
                              • 3 BA
                              • 1 HF BA
                              • Sleeps 8
                              House #3690813
                              6
                              Viewed 37 times in the last 48 hours
                                • 2 BR
                                • 2 BA
                                • 1 HF BA
                                • Sleeps 6
                                House #823516vb
                                4
                                Viewed 17 times in the last 48 hours
                                  • 3 BR
                                  • 3 BA
                                  • 1 HF BA
                                  • Sleeps 12
                                  House #508680vb
                                  1
                                  Viewed 17 times in the last 48 hours
                                    Wonderful! 4.9/5
                                    (28 reviews)
                                    avg/night
                                    • 3 BR
                                    • 3 BA
                                    • Sleeps 6
                                    House #452120vb
                                    28
                                    Viewed 37 times in the last 48 hours
                                      Wonderful! 4.8/5
                                      (21 reviews)
                                      avg/night
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 8
                                      House #733623vb
                                      21
                                      Viewed 84 times in the last 48 hours
                                        Wonderful! 4.9/5
                                        (16 reviews)
                                        avg/night
                                        • 2 BR
                                        • 2 BA
                                        • 1 HF BA
                                        • Sleeps 6
                                        House #3970025
                                        16
                                        Viewed 23 times in the last 48 hours
                                          Excellent! 4.7/5
                                          (36 reviews)
                                          avg/night
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 6
                                          House #330045
                                          36
                                          Viewed 21 times in the last 48 hours
                                            Exceptional! 5.0/5
                                            (5 reviews)
                                            avg/night
                                            • 2 BR
                                            • 2 BA
                                            • Sleeps 6
                                            House #286201vb
                                            5
                                            Viewed 30 times in the last 48 hours
                                              Excellent! 4.6/5
                                              (13 reviews)
                                              avg/night
                                              • 4 BR
                                              • 3 BA
                                              • Sleeps 8
                                              House #3747408
                                              13
                                              Viewed 45 times in the last 48 hours
                                                Exceptional! 5.0/5
                                                (24 reviews)
                                                avg/night
                                                • 6 BR
                                                • 5 BA
                                                • Sleeps 15
                                                House #512751vb
                                                24
                                                Viewed 71 times in the last 48 hours
                                                  Exceptional! 5.0/5
                                                  (12 reviews)
                                                  avg/night
                                                  • 4 BR
                                                  • 4 BA
                                                  • 1 HF BA
                                                  • Sleeps 12
                                                  House #511778vb
                                                  12
                                                  Viewed 43 times in the last 48 hours
                                                    Excellent! 4.5/5
                                                    (15 reviews)
                                                    avg/night
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 10
                                                    House #314828
                                                    15
                                                    Viewed 54 times in the last 48 hours
                                                      Exceptional! 5.0/5
                                                      (8 reviews)
                                                      avg/night
                                                      • 2 BR
                                                      • 2 BA
                                                      • 1 HF BA
                                                      • Sleeps 6
                                                      House #819589vb
                                                      8
                                                      Viewed 9 times in the last 48 hours
                                                        • 2 BR
                                                        • 2 BA
                                                        • 1 HF BA
                                                        • Sleeps 6
                                                        House #4249038
                                                        1
                                                        Viewed 19 times in the last 48 hours
                                                          Wonderful! 4.8/5
                                                          (39 reviews)
                                                          avg/night
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 5
                                                          House #164000
                                                          39
                                                          Viewed 25 times in the last 48 hours
                                                            Exceptional! 5.0/5
                                                            (26 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 2 BA
                                                            • 1 HF BA
                                                            • Sleeps 5
                                                            House #491200vb
                                                            26
                                                            Viewed 42 times in the last 48 hours
                                                              Excellent! 4.7/5
                                                              (7 reviews)
                                                              avg/night
                                                              • 4 BR
                                                              • 3 BA
                                                              • Sleeps 8
                                                              House #680648vb
                                                              7
                                                              Viewed 57 times in the last 48 hours
                                                                • 4 BR
                                                                • 3 BA
                                                                • Sleeps 10
                                                                House #822030vb
                                                                2
                                                                Viewed 30 times in the last 48 hours
                                                                  Excellent! 4.7/5
                                                                  (23 reviews)
                                                                  avg/night
                                                                  • 4 BR
                                                                  • 3 BA
                                                                  • Sleeps 12
                                                                  House #223159vb
                                                                  23
                                                                  Viewed 47 times in the last 48 hours
                                                                    Exceptional! 5.0/5
                                                                    (6 reviews)
                                                                    avg/night
                                                                    • 4 BR
                                                                    • 3 BA
                                                                    • Sleeps 10
                                                                    House #3932423
                                                                    6
                                                                    Viewed 22 times in the last 48 hours
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 8
                                                                      House #3511682
                                                                      3
                                                                      Viewed 32 times in the last 48 hours
                                                                        Exceptional! 5.0/5
                                                                        (12 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 8
                                                                        House #195489vb
                                                                        12
                                                                        Viewed 29 times in the last 48 hours
                                                                          • 4 BR
                                                                          • 2 BA
                                                                          • Sleeps 14
                                                                          House #598415vb
                                                                          Viewed 20 times in the last 48 hours
                                                                            Exceptional! 5.0/5
                                                                            (14 reviews)
                                                                            • 3 BR
                                                                            • 3 BA
                                                                            • 1 HF BA
                                                                            • Sleeps 10
                                                                            House #222618
                                                                            14
                                                                              • 4 BR
                                                                              • 4 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 12
                                                                              House #887783vb
                                                                              1
                                                                              Viewed 19 times in the last 48 hours
                                                                                Exceptional! 5.0/5
                                                                                (5 reviews)
                                                                                avg/night
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 6
                                                                                House #44822vb
                                                                                5
                                                                                Viewed 43 times in the last 48 hours
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 3 BA
                                                                                  • Sleeps 8
                                                                                  House #824353vb
                                                                                  1
                                                                                  Viewed 15 times in the last 48 hours
                                                                                    Wonderful! 4.8/5
                                                                                    (30 reviews)
                                                                                    avg/night
                                                                                    • 4 BR
                                                                                    • 4 BA
                                                                                    • Sleeps 12
                                                                                    House #311833
                                                                                    30
                                                                                    Viewed 26 times in the last 48 hours
                                                                                      Wonderful! 4.9/5
                                                                                      (7 reviews)
                                                                                      avg/night
                                                                                      • 5 BR
                                                                                      • 4 BA
                                                                                      • Sleeps 12
                                                                                      House #269212vb
                                                                                      7
                                                                                      Viewed 39 times in the last 48 hours
                                                                                        Wonderful! 4.9/5
                                                                                        (21 reviews)
                                                                                        avg/night
                                                                                        • 4 BR
                                                                                        • 4 BA
                                                                                        • Sleeps 10
                                                                                        House #455972vb
                                                                                        21
                                                                                        Viewed 46 times in the last 48 hours
                                                                                          Exceptional! 5.0/5
                                                                                          (9 reviews)
                                                                                          avg/night
                                                                                          • 4 BR
                                                                                          • 4 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 8
                                                                                          House #155410vb
                                                                                          9
                                                                                          Viewed 37 times in the last 48 hours
                                                                                            Exceptional! 5.0/5
                                                                                            (17 reviews)
                                                                                            avg/night
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 8
                                                                                            House #3719777
                                                                                            17
                                                                                            Viewed 17 times in the last 48 hours
                                                                                              avg/night
                                                                                              • 3 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 10
                                                                                              House #597222vb
                                                                                              2
                                                                                              Viewed 8 times in the last 48 hours
                                                                                                • 5 BR
                                                                                                • 6 BA
                                                                                                • Sleeps 18
                                                                                                House #831013vb
                                                                                                Viewed 38 times in the last 48 hours
                                                                                                  Excellent! 4.7/5
                                                                                                  (33 reviews)
                                                                                                  avg/night
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 8
                                                                                                  House #21837vb
                                                                                                  33
                                                                                                  Viewed 26 times in the last 48 hours
                                                                                                    avg/night
                                                                                                    • 4 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 6
                                                                                                    House #3879557
                                                                                                    3
                                                                                                    Viewed 10 times in the last 48 hours
                                                                                                      Wonderful! 4.9/5
                                                                                                      (49 reviews)
                                                                                                      avg/night
                                                                                                      • 3 BR
                                                                                                      • 3 BA
                                                                                                      • Sleeps 9
                                                                                                      House #289436vb
                                                                                                      49
                                                                                                      Viewed 26 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Upper Florida Keys Reviews

                                                                                                      Perfectly appointed and fit our family of 5 (ages 13, 11 and 8) perfectly!

                                                                                                      5 of 5
                                                                                                      Close to the pool and all Islamorada attractions! Very clean and beautifully updated. Stocked with all the basics and we even got a "starter kit" with dish, soap and laundry detergent. We didn't need much more to get us through! We felt immediately at home here and will definitely stay again! The perfect family vacation spot!
                                                                                                      • Submitted: Nov 29, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Perfectly getaway spot.

                                                                                                      5 of 5
                                                                                                      Exquisite views. Amazing grounds and property. Crystal blue pool overlooking ocean and docks. Charming Key west style townhouses dot the cozy community. The unit we stayed had adorable tropical touches, comfortable bedding and thoughtful amenities. Enjoyed sitting on the front porch overlooking the coastal scenery. We can't wait to go back.
                                                                                                      • Submitted: Nov 8, 2016
                                                                                                      • Stayed: Oct 2016

                                                                                                      Beautiful grounds and very nice home

                                                                                                      5 of 5
                                                                                                      Chris was very easy to work with and the house was very nice. The community was beautiful and the pool was very nice and the temperature was perfect!! We have already recommended this place to friends and will definitely come back the next time we are in the Keys.
                                                                                                      • Submitted: Nov 1, 2016
                                                                                                      • Stayed: Oct 2016