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Grassy Key: Houses, Condos & More (300+)

  • 1 - 50 of 300+
Additional fees apply. Taxes may be added.
    Wonderful! 4.8/5
    (23 reviews)
    avg/night
    • 1 BR
    • 1 BA
    • Sleeps 2
    Cottage #771927vb
    23
    Viewed 67 times in the last 48 hours
      avg/night
      • 2 BR
      • 1 BA
      • 1 HF BA
      • Sleeps 6
      Mobile Home #967477vb
      Viewed 52 times in the last 48 hours
        Very Good! 4.1/5
        (7 reviews)
        avg/night
        • 3 BR
        • 2 BA
        • Sleeps 8
        House #632067vb
        7
        Viewed 45 times in the last 48 hours
          Exceptional! 5.0/5
          (21 reviews)
          avg/night
          • 4 BR
          • 2 BA
          • 1 HF BA
          • Sleeps 10
          House #773860vb
          21
          Viewed 22 times in the last 48 hours
            • 4 BR
            • 3 BA
            • Sleeps 10
            House #856384vb
            1 Review
            Viewed 37 times in the last 48 hours
              Exceptional! 5.0/5
              (13 reviews)
              avg/night
              • 3 BR
              • 2 BA
              • Sleeps 6
              House #664538vb
              13
              Viewed 15 times in the last 48 hours
                avg/night
                • 1 BR
                • 1 BA
                • Sleeps 8
                Apartment #931033vb
                Viewed 73 times in the last 48 hours
                  Wonderful! 4.9/5
                  (55 reviews)
                  avg/night
                  • Studio
                  • 1 BA
                  • Sleeps 2
                  Studio #62467vb
                  55
                  Viewed 16 times in the last 48 hours
                    Excellent! 4.3/5
                    (16 reviews)
                    avg/night
                    • 1 BR
                    • 1 BA
                    • Sleeps 8
                    Apartment #579582vb
                    16
                    Viewed 97 times in the last 48 hours
                      Wonderful! 4.9/5
                      (53 reviews)
                      avg/night
                      • 1 BR
                      • 1 BA
                      • Sleeps 2
                      Apartment #646192vb
                      53
                      Viewed 48 times in the last 48 hours
                        Wonderful! 4.9/5
                        (22 reviews)
                        avg/night
                        • 2 BR
                        • 2 BA
                        • Sleeps 6
                        House #24590vb
                        22
                        Viewed 14 times in the last 48 hours
                          Wonderful! 4.9/5
                          (18 reviews)
                          avg/night
                          • 1 BR
                          • 1 BA
                          • Sleeps 2
                          Apartment #790012vb
                          18
                          Viewed 43 times in the last 48 hours
                            Wonderful! 4.9/5
                            (50 reviews)
                            avg/night
                            • 3 BR
                            • 3 BA
                            • Sleeps 8
                            Villa #312620vb
                            50
                            Viewed 32 times in the last 48 hours
                              Exceptional! 5.0/5
                              (37 reviews)
                              avg/night
                              • 3 BR
                              • 3 BA
                              • Sleeps 8
                              House #507889vb
                              37
                              Viewed 27 times in the last 48 hours
                                Exceptional! 5.0/5
                                (26 reviews)
                                avg/night
                                • 2 BR
                                • 2 BA
                                • Sleeps 8
                                Cottage #3921613
                                26
                                Viewed 46 times in the last 48 hours
                                  Exceptional! 5.0/5
                                  (103 reviews)
                                  avg/night
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 6
                                  House #374434vb
                                  103
                                  Viewed 38 times in the last 48 hours
                                    avg/night
                                    • Studio
                                    • 1 BA
                                    • Sleeps 2
                                    Studio #876256vb
                                    Viewed 6 times in the last 48 hours
                                      avg/night
                                      • Studio
                                      • 1 BA
                                      • Sleeps 2
                                      Studio #876250vb
                                      1 Review
                                      Viewed 52 times in the last 48 hours
                                        avg/night
                                        • Studio
                                        • 1 BA
                                        • Sleeps 2
                                        Studio #876049vb
                                        3
                                        Viewed 14 times in the last 48 hours
                                          • Studio
                                          • 1 BA
                                          • Sleeps 2
                                          Studio #875991vb
                                          Viewed 8 times in the last 48 hours
                                            Excellent! 4.3/5
                                            (7 reviews)
                                            avg/night
                                            • 3 BR
                                            • 3 BA
                                            • Sleeps 12
                                            Cottage #3932582
                                            7
                                            Viewed 15 times in the last 48 hours
                                              avg/night
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 8
                                              House #681227vb
                                              4
                                              Viewed 9 times in the last 48 hours
                                                avg/night
                                                • 5 BR
                                                • 3 BA
                                                • Sleeps 10
                                                House #795639vb
                                                2 Reviews
                                                Viewed 21 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (39 reviews)
                                                  avg/night
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  Townhome #148439vb
                                                  39
                                                  Viewed 43 times in the last 48 hours
                                                    Exceptional! 5.0/5
                                                    (25 reviews)
                                                    avg/night
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 8
                                                    Condo #488244vb
                                                    25
                                                    Viewed 26 times in the last 48 hours
                                                      Wonderful! 4.9/5
                                                      (49 reviews)
                                                      avg/night
                                                      • 2 BR
                                                      • 1 BA
                                                      • 1 HF BA
                                                      • Sleeps 5
                                                      House #602398vb
                                                      49
                                                      Viewed 111 times in the last 48 hours
                                                        Excellent! 4.7/5
                                                        (14 reviews)
                                                        avg/night
                                                        • 1 BR
                                                        • 1 BA
                                                        • Sleeps 4
                                                        Mobile Home #734155vb
                                                        14
                                                        Viewed 28 times in the last 48 hours
                                                          Excellent! 4.7/5
                                                          (14 reviews)
                                                          avg/night
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 4
                                                          House #751915vb
                                                          14
                                                          Viewed 48 times in the last 48 hours
                                                            avg/night
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 2
                                                            Cottage #788832vb
                                                            Viewed 20 times in the last 48 hours
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              Condo #4317164
                                                              Viewed 60 times in the last 48 hours
                                                                Good! 3.9/5
                                                                (28 reviews)
                                                                avg/night
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                Apartment #449249vb
                                                                28
                                                                Viewed 40 times in the last 48 hours
                                                                  Excellent! 4.6/5
                                                                  (5 reviews)
                                                                  avg/night
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 4
                                                                  Condo #477338vb
                                                                  5
                                                                  Viewed 12 times in the last 48 hours
                                                                    Wonderful! 4.9/5
                                                                    (13 reviews)
                                                                    avg/night
                                                                    • 4 BR
                                                                    • 3 BA
                                                                    • Sleeps 10
                                                                    House #504807vb
                                                                    13
                                                                    Viewed 27 times in the last 48 hours
                                                                      • 4 BR
                                                                      • 3 BA
                                                                      • Sleeps 10
                                                                      Villa #928934vb
                                                                      Viewed 36 times in the last 48 hours
                                                                        avg/night
                                                                        • 2 BR
                                                                        • 2 BA
                                                                        • Sleeps 5
                                                                        House #7027791
                                                                        1 Review
                                                                        Viewed 11 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (14 reviews)
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 5
                                                                          House #324569vb
                                                                          14
                                                                          Viewed 26 times in the last 48 hours
                                                                            Exceptional! 5.0/5
                                                                            (5 reviews)
                                                                            avg/night
                                                                            • 4 BR
                                                                            • 4 BA
                                                                            • Sleeps 10
                                                                            House #361717vb
                                                                            5
                                                                            Viewed 20 times in the last 48 hours
                                                                              Exceptional! 5.0/5
                                                                              (50 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Sleeps 4
                                                                              House #648466vb
                                                                              50
                                                                              Viewed 16 times in the last 48 hours
                                                                                avg/night
                                                                                • 4 BR
                                                                                • 3 BA
                                                                                • Sleeps 10
                                                                                House #4275944
                                                                                Viewed 47 times in the last 48 hours
                                                                                  • 2 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 5
                                                                                  House #926352vb
                                                                                  Viewed 35 times in the last 48 hours
                                                                                    • 4 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 10
                                                                                    House #925338vb
                                                                                    4
                                                                                    Viewed 48 times in the last 48 hours
                                                                                      Wonderful! 4.9/5
                                                                                      (19 reviews)
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 6
                                                                                      House #264471
                                                                                      19
                                                                                      Viewed 10 times in the last 48 hours
                                                                                        Excellent! 4.4/5
                                                                                        (18 reviews)
                                                                                        avg/night
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        Condo #3654428
                                                                                        18
                                                                                        Viewed 60 times in the last 48 hours
                                                                                          Wonderful! 4.8/5
                                                                                          (9 reviews)
                                                                                          avg/night
                                                                                          • Studio
                                                                                          • 1 BA
                                                                                          • Sleeps 2
                                                                                          Studio #788109vb
                                                                                          9
                                                                                          Viewed 90 times in the last 48 hours
                                                                                            avg/night
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 4
                                                                                            Apartment #4278070
                                                                                            Viewed 54 times in the last 48 hours
                                                                                              Wonderful! 4.8/5
                                                                                              (28 reviews)
                                                                                              avg/night
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              Condo #22721vb
                                                                                              28
                                                                                              Viewed 40 times in the last 48 hours
                                                                                                • 3 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 8
                                                                                                Cottage #345333
                                                                                                4
                                                                                                Viewed 47 times in the last 48 hours
                                                                                                  Exceptional! 5.0/5
                                                                                                  (6 reviews)
                                                                                                  avg/night
                                                                                                  • 3 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 8
                                                                                                  Villa #456926vb
                                                                                                  6
                                                                                                  Viewed 38 times in the last 48 hours
                                                                                                    • 2 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 4
                                                                                                    House #477067vb
                                                                                                    1 Review
                                                                                                    Viewed 38 times in the last 48 hours
                                                                                                      Wonderful! 4.8/5
                                                                                                      (30 reviews)
                                                                                                      avg/night
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 6
                                                                                                      House #497296vb
                                                                                                      30
                                                                                                      Viewed 18 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Grassy Key Reviews

                                                                                                      Great house in a great location!!!

                                                                                                      5 of 5
                                                                                                      19 of us rented two houses right next door so we could spend Thanksgivih week together! Jay and Sherry are amazing host!! We just love them! So much so that we were just here in March and rented through them! And plan to use them every time we return!!!
                                                                                                      • Submitted: Nov 27, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Beautiful home away from home

                                                                                                      5 of 5
                                                                                                      Four siblings made the Vacation Tide Cottage our get away retreat. We found the "cottage" to be much more than a cottage. It was a spacious, clean and modern place to stay. The kitchen was well stocked and we made good use of it. The views from the balconies were beautiful. We especially enjoyed all the wildlife that foraged in the mud flats around the building. We saw white and brown pelicans, trip-colored, gold-crowed, small blue, great blue and white herons, great white, cattle and reddish egrets, white ibis and many other small shore birds. Unfortunately, the weather wasn't the best while we were there so we didn't get to take advantage of the kayaks and bikes. Perhaps another time?!? The cottage has several games and we did use them when it was too windy and rainy. We would definitely consider staying here again.
                                                                                                      • Submitted: Nov 11, 2016
                                                                                                      • Stayed: Oct 2016

                                                                                                      First time Florida vacation

                                                                                                      4 of 5
                                                                                                      A house large enough to accommodate 10 people was beautiful and well maintained. We had plenty of room, and with the ocean right out the door. Only downside was 2 things it had no beach and sadly a foul smell of sewer here and around the keys. Had no problems with the owners they even bought new fishing poles since previous renters broken them. Did 2 fishing charters, swam with the dolphins, ate at several seafood restaurants. Sad when time to go.
                                                                                                      • Submitted: Oct 16, 2016
                                                                                                      • Stayed: Oct 2016