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  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
    Wonderful! 4.9/5
    (45 reviews)
    avg/night
    • 1 BR
    • 2 BA
    • Sleeps 6
    Condo #56577vb
    45
    Viewed 130 times in the last 48 hours
      Exceptional! 5.0/5
      (50 reviews)
      avg/night
      • 3 BR
      • 2 BA
      • Sleeps 8
      Condo #439219vb
      50
      Viewed 278 times in the last 48 hours
        Wonderful! 4.9/5
        (50 reviews)
        avg/night
        • 2 BR
        • 2 BA
        • Sleeps 6
        Condo #7068732
        50
        Viewed 349 times in the last 48 hours
          Excellent! 4.7/5
          (38 reviews)
          avg/night
          • 2 BR
          • 2 BA
          • Sleeps 6
          Condo #454596vb
          38
          Viewed 94 times in the last 48 hours
            Wonderful! 4.9/5
            (35 reviews)
            avg/night
            • 2 BR
            • 2 BA
            • 1 HF BA
            • Sleeps 6
            Condo #295795vb
            35
            Viewed 76 times in the last 48 hours
              Exceptional! 5.0/5
              (5 reviews)
              avg/night
              • 3 BR
              • 2 BA
              • 1 HF BA
              • Sleeps 8
              Condo #789763vb
              5
              Viewed 103 times in the last 48 hours
                Exceptional! 5.0/5
                (16 reviews)
                avg/night
                • 2 BR
                • 2 BA
                • Sleeps 6
                Condo #715746vb
                16
                Viewed 118 times in the last 48 hours
                  Wonderful! 4.8/5
                  (17 reviews)
                  avg/night
                  • 1 BR
                  • 2 BA
                  • Sleeps 6
                  Condo #769044vb
                  17
                  Viewed 90 times in the last 48 hours
                    Excellent! 4.7/5
                    (51 reviews)
                    avg/night
                    • 1 BR
                    • 1 BA
                    • Sleeps 6
                    Condo #567974vb
                    51
                    Viewed 78 times in the last 48 hours
                      Wonderful! 4.9/5
                      (27 reviews)
                      avg/night
                      • 1 BR
                      • 2 BA
                      • Sleeps 6
                      Condo #290378vb
                      27
                      Viewed 176 times in the last 48 hours
                        Wonderful! 4.8/5
                        (32 reviews)
                        avg/night
                        • 1 BR
                        • 1 BA
                        • 1 HF BA
                        • Sleeps 6
                        Condo #622497vb
                        32
                        Viewed 52 times in the last 48 hours
                          Excellent! 4.7/5
                          (23 reviews)
                          avg/night
                          • 1 BR
                          • 1 BA
                          • Sleeps 2
                          Condo #682088vb
                          23
                          Viewed 318 times in the last 48 hours
                            Wonderful! 4.8/5
                            (46 reviews)
                            avg/night
                            • 1 BR
                            • 1 BA
                            • 1 HF BA
                            • Sleeps 2
                            Condo #514030vb
                            46
                            Viewed 245 times in the last 48 hours
                              Wonderful! 4.9/5
                              (70 reviews)
                              avg/night
                              • 3 BR
                              • 3 BA
                              • Sleeps 11
                              Condo #169467
                              70
                              Viewed 439 times in the last 48 hours
                                Wonderful! 4.8/5
                                (63 reviews)
                                avg/night
                                • 1 BR
                                • 1 BA
                                • 1 HF BA
                                • Sleeps 4
                                Condo #417779vb
                                63
                                Viewed 198 times in the last 48 hours
                                  Wonderful! 4.8/5
                                  (14 reviews)
                                  avg/night
                                  • 1 BR
                                  • 1 BA
                                  • 1 HF BA
                                  • Sleeps 6
                                  Condo #741061vb
                                  14
                                  Viewed 427 times in the last 48 hours
                                    Exceptional! 5.0/5
                                    (59 reviews)
                                    avg/night
                                    • 3 BR
                                    • 3 BA
                                    • Sleeps 8
                                    Condo #398888vb
                                    59
                                    Viewed 313 times in the last 48 hours
                                      Wonderful! 4.8/5
                                      (10 reviews)
                                      avg/night
                                      • 3 BR
                                      • 2 BA
                                      • 1 HF BA
                                      • Sleeps 8
                                      Condo #840418vb
                                      10
                                      Viewed 273 times in the last 48 hours
                                        Excellent! 4.6/5
                                        (21 reviews)
                                        $70
                                        avg/night
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 4
                                        Condo #622644vb
                                        21
                                        Viewed 267 times in the last 48 hours
                                          Exceptional! 5.0/5
                                          (28 reviews)
                                          avg/night
                                          • 1 BR
                                          • 1 BA
                                          • 1 HF BA
                                          • Sleeps 6
                                          Condo #767359vb
                                          28
                                          Viewed 294 times in the last 48 hours
                                            Wonderful! 4.9/5
                                            (48 reviews)
                                            avg/night
                                            • 2 BR
                                            • 2 BA
                                            • 1 HF BA
                                            • Sleeps 8
                                            Condo #721815vb
                                            48
                                            Viewed 257 times in the last 48 hours
                                              Wonderful! 4.9/5
                                              (34 reviews)
                                              avg/night
                                              • 1 BR
                                              • 2 BA
                                              • Sleeps 4
                                              Condo #376141vb
                                              34
                                              Viewed 137 times in the last 48 hours
                                                Wonderful! 4.9/5
                                                (54 reviews)
                                                $87
                                                avg/night
                                                • Studio
                                                • 1 BA
                                                • Sleeps 2
                                                Condo #686738vb
                                                54
                                                Viewed 196 times in the last 48 hours
                                                  Exceptional! 5.0/5
                                                  (5 reviews)
                                                  avg/night
                                                  • 3 BR
                                                  • 3 BA
                                                  • Sleeps 8
                                                  Condo #455309vb
                                                  5
                                                  Viewed 113 times in the last 48 hours
                                                    Excellent! 4.5/5
                                                    (34 reviews)
                                                    avg/night
                                                    • 3 BR
                                                    • 3 BA
                                                    • Sleeps 11
                                                    Condo #475054vb
                                                    34
                                                    Viewed 173 times in the last 48 hours
                                                      Wonderful! 4.9/5
                                                      (103 reviews)
                                                      avg/night
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      Condo #151307
                                                      103
                                                      Viewed 41 times in the last 48 hours
                                                        Excellent! 4.7/5
                                                        (6 reviews)
                                                        avg/night
                                                        • 1 BR
                                                        • 1 BA
                                                        • 1 HF BA
                                                        • Sleeps 6
                                                        Condo #603500vb
                                                        6
                                                        Viewed 132 times in the last 48 hours
                                                          Wonderful! 4.8/5
                                                          (17 reviews)
                                                          avg/night
                                                          • 3 BR
                                                          • 3 BA
                                                          • Sleeps 8
                                                          Condo #783524vb
                                                          17
                                                          Viewed 149 times in the last 48 hours
                                                            Wonderful! 4.9/5
                                                            (12 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 6
                                                            Condo #119398vb
                                                            12
                                                            Viewed 241 times in the last 48 hours
                                                              Excellent! 4.6/5
                                                              (32 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              Condo #481015vb
                                                              32
                                                              Viewed 144 times in the last 48 hours
                                                                Wonderful! 4.8/5
                                                                (29 reviews)
                                                                avg/night
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                Condo #652581vb
                                                                29
                                                                Viewed 99 times in the last 48 hours
                                                                  Wonderful! 4.9/5
                                                                  (17 reviews)
                                                                  avg/night
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 8
                                                                  Condo #459320vb
                                                                  17
                                                                  Viewed 76 times in the last 48 hours
                                                                    Wonderful! 4.8/5
                                                                    (11 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 10
                                                                    Condo #793581vb
                                                                    11
                                                                    Viewed 133 times in the last 48 hours
                                                                      Excellent! 4.7/5
                                                                      (81 reviews)
                                                                      avg/night
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      Condo #236359vb
                                                                      81
                                                                      Viewed 294 times in the last 48 hours
                                                                        Excellent! 4.7/5
                                                                        (22 reviews)
                                                                        avg/night
                                                                        • 2 BR
                                                                        • 2 BA
                                                                        • Sleeps 6
                                                                        Condo #488253vb
                                                                        22
                                                                        Viewed 159 times in the last 48 hours
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 8
                                                                          Condo #570636vb
                                                                          1
                                                                          Viewed 240 times in the last 48 hours
                                                                            Excellent! 4.7/5
                                                                            (54 reviews)
                                                                            avg/night
                                                                            • 2 BR
                                                                            • 2 BA
                                                                            • Sleeps 8
                                                                            Condo #113143vb
                                                                            54
                                                                            Viewed 76 times in the last 48 hours
                                                                              Excellent! 4.7/5
                                                                              (20 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              Condo #141095vb
                                                                              20
                                                                              Viewed 287 times in the last 48 hours
                                                                                Excellent! 4.7/5
                                                                                (34 reviews)
                                                                                avg/night
                                                                                • 2 BR
                                                                                • 2 BA
                                                                                • Sleeps 6
                                                                                Condo #502869vb
                                                                                34
                                                                                Viewed 135 times in the last 48 hours
                                                                                  Exceptional! 5.0/5
                                                                                  (32 reviews)
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 3 BA
                                                                                  • Sleeps 8
                                                                                  Condo #673339vb
                                                                                  32
                                                                                  Viewed 126 times in the last 48 hours
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 8
                                                                                    Condo #765931vb
                                                                                    4
                                                                                    Viewed 83 times in the last 48 hours
                                                                                      Wonderful! 4.8/5
                                                                                      (58 reviews)
                                                                                      avg/night
                                                                                      • 1 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 6
                                                                                      Condo #86433vb
                                                                                      58
                                                                                      Viewed 147 times in the last 48 hours
                                                                                        Excellent! 4.6/5
                                                                                        (48 reviews)
                                                                                        avg/night
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        Condo #326434vb
                                                                                        48
                                                                                        Viewed 321 times in the last 48 hours
                                                                                          Very Good! 4.0/5
                                                                                          (8 reviews)
                                                                                          avg/night
                                                                                          • 1 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                          Condo #781964vb
                                                                                          8
                                                                                          Viewed 149 times in the last 48 hours
                                                                                            Wonderful! 4.8/5
                                                                                            (40 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 6
                                                                                            Condo #280428vb
                                                                                            40
                                                                                            Viewed 190 times in the last 48 hours
                                                                                              Wonderful! 4.9/5
                                                                                              (27 reviews)
                                                                                              avg/night
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 8
                                                                                              Condo #376925vb
                                                                                              27
                                                                                              Viewed 92 times in the last 48 hours
                                                                                                • 2 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 6
                                                                                                Condo #668821vb
                                                                                                1
                                                                                                Viewed 35 times in the last 48 hours
                                                                                                  Wonderful! 4.8/5
                                                                                                  (37 reviews)
                                                                                                  avg/night
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  Condo #418742vb
                                                                                                  37
                                                                                                  Viewed 144 times in the last 48 hours
                                                                                                    Exceptional! 5.0/5
                                                                                                    (27 reviews)
                                                                                                    avg/night
                                                                                                    • 1 BR
                                                                                                    • 1 BA
                                                                                                    • 1 HF BA
                                                                                                    • Sleeps 6
                                                                                                    Condo #508276vb
                                                                                                    27
                                                                                                    Viewed 159 times in the last 48 hours
                                                                                                      Excellent! 4.4/5
                                                                                                      (5 reviews)
                                                                                                      avg/night
                                                                                                      • 1 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 6
                                                                                                      Condo #611862vb
                                                                                                      5
                                                                                                      Viewed 95 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Leeward Key Reviews

                                                                                                      Wonderful!!!!

                                                                                                      5 of 5
                                                                                                      This is my second time renting from Mike and Tracy and I absolutely loved this home. It is directly across the street from the beach and the condominiums are very quiet. We had plenty space and everything was nice and clean upon our arrival. I am big on customer service as well and Tracy has always been very pleasant with both of my stays.
                                                                                                      • Submitted: Jan 3, 2017
                                                                                                      • Stayed: Dec 2016

                                                                                                      Fabulous area and condo!

                                                                                                      5 of 5
                                                                                                      We loved it! We took our 3 young children, and another couple with 3 children, and there was so much room for the kids to play and run around. Everything we needed was provided, and great tub to wash the sands off little bottoms (and big ones, too!). The beach is great with soft, white sands so no feet were burning! Area is great and close to necessities. Great running/jogging area. Will return! Thanks so much!
                                                                                                      • Submitted: Sep 30, 2008
                                                                                                      • Stayed: Sep 2008

                                                                                                      Guestbook Comment

                                                                                                      5 of 5
                                                                                                      My parents just came back from Greg's condo in Destin. They loved it. They go to Destin 4 times a year, and by far this is their favorite condo. They have booked for next October. My husband and I booked this for them knowing they would love it. Greg is wonderful to deal with. Condo is great! Thanks Greg!
                                                                                                      • Submitted: Oct 16, 2007
                                                                                                      • Stayed: Oct 2007