check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit
  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
  View map Map
    Excellent! 4.7/5
    (21 reviews)
    avg/night
    • 3 BR
    • 2 BA
    • Sleeps 11
    Cottage #3653537
    21
    Viewed 205 times in the last 48 hours
      Wonderful! 4.9/5
      (40 reviews)
      avg/night
      • 3 BR
      • 3 BA
      • Sleeps 8
      Cottage #396882vb
      40
      Viewed 63 times in the last 48 hours
        Wonderful! 4.9/5
        (40 reviews)
        avg/night
        • 2 BR
        • 2 BA
        • Sleeps 6
        Cottage #170775vb
        40
        Viewed 24 times in the last 48 hours
          Wonderful! 4.8/5
          (22 reviews)
          avg/night
          • 3 BR
          • 1 BA
          • 1 HF BA
          • Sleeps 9
          Cottage #510252vb
          22
          Viewed 103 times in the last 48 hours
            Exceptional! 5.0/5
            (6 reviews)
            avg/night
            • 4 BR
            • 3 BA
            • Sleeps 12
            Cottage #782591vb
            6
            Viewed 83 times in the last 48 hours
              Wonderful! 4.8/5
              (41 reviews)
              avg/night
              • 1 BR
              • 1 BA
              • Sleeps 2
              Cottage #219335vb
              41
              Viewed 178 times in the last 48 hours
                Wonderful! 4.8/5
                (38 reviews)
                avg/night
                • 2 BR
                • 2 BA
                • Sleeps 5
                Cottage #188200vb
                38
                Viewed 129 times in the last 48 hours
                  Wonderful! 4.8/5
                  (28 reviews)
                  avg/night
                  • 3 BR
                  • 2 BA
                  • Sleeps 6
                  Cottage #253845vb
                  28
                  Viewed 113 times in the last 48 hours
                    Wonderful! 4.8/5
                    (9 reviews)
                    avg/night
                    • 2 BR
                    • 2 BA
                    • 1 HF BA
                    • Sleeps 8
                    Cottage #13215vb
                    9
                    Viewed 53 times in the last 48 hours
                      Wonderful! 4.9/5
                      (24 reviews)
                      avg/night
                      • 3 BR
                      • 2 BA
                      • 1 HF BA
                      • Sleeps 8
                      Cottage #221548vb
                      24
                      Viewed 158 times in the last 48 hours
                        Excellent! 4.6/5
                        (11 reviews)
                        avg/night
                        • 3 BR
                        • 3 BA
                        • Sleeps 12
                        Cottage #120639vb
                        11
                        Viewed 209 times in the last 48 hours
                          Very Good! 4.2/5
                          (29 reviews)
                          avg/night
                          • 2 BR
                          • 2 BA
                          • Sleeps 6
                          Cottage #193084vb
                          29
                          Viewed 230 times in the last 48 hours
                            Exceptional! 5.0/5
                            (15 reviews)
                            avg/night
                            • 4 BR
                            • 3 BA
                            • 1 HF BA
                            • Sleeps 12
                            Cottage #704217vb
                            15
                            Viewed 166 times in the last 48 hours
                              Exceptional! 5.0/5
                              (27 reviews)
                              avg/night
                              • 3 BR
                              • 2 BA
                              • Sleeps 8
                              Cottage #584922vb
                              27
                              Viewed 80 times in the last 48 hours
                                Wonderful! 4.9/5
                                (15 reviews)
                                avg/night
                                • 1 BR
                                • 2 BA
                                • Sleeps 4
                                Cottage #77431vb
                                15
                                Viewed 117 times in the last 48 hours
                                  Wonderful! 4.8/5
                                  (12 reviews)
                                  avg/night
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 8
                                  Cottage #887475vb
                                  12
                                  Viewed 43 times in the last 48 hours
                                    Excellent! 4.6/5
                                    (15 reviews)
                                    avg/night
                                    • 2 BR
                                    • 3 BA
                                    • Sleeps 6
                                    Cottage #382416vb
                                    15
                                    Viewed 64 times in the last 48 hours
                                      Excellent! 4.7/5
                                      (10 reviews)
                                      avg/night
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 12
                                      Cottage #653181vb
                                      10
                                      Viewed 114 times in the last 48 hours
                                        Wonderful! 4.8/5
                                        (9 reviews)
                                        avg/night
                                        • 2 BR
                                        • 2 BA
                                        • 1 HF BA
                                        • Sleeps 8
                                        Cottage #726686vb
                                        9
                                        Viewed 68 times in the last 48 hours
                                          Wonderful! 4.9/5
                                          (56 reviews)
                                          avg/night
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 8
                                          Cottage #477915vb
                                          56
                                          Viewed 114 times in the last 48 hours
                                            Excellent! 4.6/5
                                            (28 reviews)
                                            avg/night
                                            • 4 BR
                                            • 3 BA
                                            • Sleeps 8
                                            Cottage #292024vb
                                            28
                                            Viewed 80 times in the last 48 hours
                                              avg/night
                                              • 1 BR
                                              • 1 BA
                                              • 1 HF BA
                                              • Sleeps 3
                                              Cottage #873051vb
                                              3
                                              Viewed 112 times in the last 48 hours
                                                Wonderful! 4.8/5
                                                (21 reviews)
                                                avg/night
                                                • 3 BR
                                                • 3 BA
                                                • Sleeps 6
                                                Cottage #77425vb
                                                21
                                                Viewed 76 times in the last 48 hours
                                                  Wonderful! 4.8/5
                                                  (25 reviews)
                                                  avg/night
                                                  • 10 BR
                                                  • 10 BA
                                                  • 1 HF BA
                                                  • Sleeps 22
                                                  Cottage #583916vb
                                                  25
                                                  Viewed 114 times in the last 48 hours
                                                    Excellent! 4.5/5
                                                    (22 reviews)
                                                    avg/night
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    Cottage #580482vb
                                                    22
                                                    Viewed 94 times in the last 48 hours
                                                      avg/night
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 4
                                                      Cottage #563397vb
                                                      6
                                                      Viewed 95 times in the last 48 hours
                                                        Wonderful! 4.9/5
                                                        (15 reviews)
                                                        avg/night
                                                        • 4 BR
                                                        • 3 BA
                                                        • 1 HF BA
                                                        • Sleeps 12
                                                        Cottage #674360vb
                                                        15
                                                        Viewed 119 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (15 reviews)
                                                          avg/night
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                          Cottage #304025vb
                                                          15
                                                          Viewed 115 times in the last 48 hours
                                                            Excellent! 4.5/5
                                                            (8 reviews)
                                                            avg/night
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            Cottage #224372vb
                                                            8
                                                            Viewed 55 times in the last 48 hours
                                                              Exceptional! 5.0/5
                                                              (14 reviews)
                                                              avg/night
                                                              • 3 BR
                                                              • 3 BA
                                                              • Sleeps 8
                                                              Cottage #862890vb
                                                              14
                                                              Viewed 154 times in the last 48 hours
                                                                • 3 BR
                                                                • 2 BA
                                                                • 1 HF BA
                                                                • Sleeps 6
                                                                Cottage #489416vb
                                                                4
                                                                Viewed 114 times in the last 48 hours
                                                                  Exceptional! 5.0/5
                                                                  (21 reviews)
                                                                  avg/night
                                                                  • 3 BR
                                                                  • 3 BA
                                                                  • Sleeps 10
                                                                  Cottage #481594vb
                                                                  21
                                                                  Viewed 91 times in the last 48 hours
                                                                    Excellent! 4.7/5
                                                                    (24 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 3 BA
                                                                    • Sleeps 8
                                                                    Cottage #221555vb
                                                                    24
                                                                    Viewed 58 times in the last 48 hours
                                                                      Wonderful! 4.8/5
                                                                      (47 reviews)
                                                                      avg/night
                                                                      • 2 BR
                                                                      • 2 BA
                                                                      • Sleeps 4
                                                                      Cottage #221553vb
                                                                      47
                                                                      Viewed 80 times in the last 48 hours
                                                                        avg/night
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 4
                                                                        Cottage #206420vb
                                                                        2
                                                                        Viewed 91 times in the last 48 hours
                                                                          Excellent! 4.3/5
                                                                          (33 reviews)
                                                                          avg/night
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 2
                                                                          Cottage #291898vb
                                                                          33
                                                                          Viewed 107 times in the last 48 hours
                                                                            Wonderful! 4.8/5
                                                                            (24 reviews)
                                                                            avg/night
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • 1 HF BA
                                                                            • Sleeps 10
                                                                            Cottage #280874vb
                                                                            24
                                                                            Viewed 68 times in the last 48 hours
                                                                              Wonderful! 4.8/5
                                                                              (6 reviews)
                                                                              avg/night
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              Cottage #864518vb
                                                                              6
                                                                              Viewed 80 times in the last 48 hours
                                                                                Exceptional! 5.0/5
                                                                                (9 reviews)
                                                                                avg/night
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 2
                                                                                Cottage #695462vb
                                                                                9
                                                                                Viewed 33 times in the last 48 hours
                                                                                  Wonderful! 4.9/5
                                                                                  (85 reviews)
                                                                                  avg/night
                                                                                  • 2 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  Cottage #13478vb
                                                                                  85
                                                                                  Viewed 93 times in the last 48 hours
                                                                                    Excellent! 4.7/5
                                                                                    (18 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 4
                                                                                    Cottage #77303vb
                                                                                    18
                                                                                    Viewed 87 times in the last 48 hours
                                                                                      Wonderful! 4.9/5
                                                                                      (36 reviews)
                                                                                      avg/night
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 2
                                                                                      Cottage #306353
                                                                                      36
                                                                                      Viewed 57 times in the last 48 hours
                                                                                        Wonderful! 4.9/5
                                                                                        (34 reviews)
                                                                                        avg/night
                                                                                        • 4 BR
                                                                                        • 4 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 10
                                                                                        Cottage #382101vb
                                                                                        34
                                                                                        Viewed 231 times in the last 48 hours
                                                                                          Wonderful! 4.9/5
                                                                                          (13 reviews)
                                                                                          avg/night
                                                                                          • 4 BR
                                                                                          • 4 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 10
                                                                                          Cottage #334105vb
                                                                                          13
                                                                                          Viewed 70 times in the last 48 hours
                                                                                            Wonderful! 4.9/5
                                                                                            (7 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 5
                                                                                            Cottage #436323vb
                                                                                            7
                                                                                            Viewed 80 times in the last 48 hours
                                                                                              Exceptional! 5.0/5
                                                                                              (32 reviews)
                                                                                              avg/night
                                                                                              • 4 BR
                                                                                              • 2 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 10
                                                                                              Cottage #362199vb
                                                                                              32
                                                                                              Viewed 186 times in the last 48 hours
                                                                                                Exceptional! 5.0/5
                                                                                                (8 reviews)
                                                                                                avg/night
                                                                                                • 2 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 6
                                                                                                Cottage #291884vb
                                                                                                8
                                                                                                Viewed 78 times in the last 48 hours
                                                                                                  Wonderful! 4.8/5
                                                                                                  (20 reviews)
                                                                                                  avg/night
                                                                                                  • 4 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 9
                                                                                                  Cottage #336656vb
                                                                                                  20
                                                                                                  Viewed 43 times in the last 48 hours
                                                                                                    Exceptional! 5.0/5
                                                                                                    (6 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 6
                                                                                                    Cottage #784008vb
                                                                                                    6
                                                                                                    Viewed 23 times in the last 48 hours
                                                                                                      Excellent! 4.7/5
                                                                                                      (35 reviews)
                                                                                                      avg/night
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 9
                                                                                                      Cottage #438458vb
                                                                                                      35
                                                                                                      Viewed 115 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Leeward Key Reviews

                                                                                                      Great place close to everything!

                                                                                                      4 of 5
                                                                                                      Couple glitches but nothing major, plenty of towels, dishes and cooking utensils was clean, big, and nice pool. A couple blocks either way is the beach or great shopping! Will definitely be back with our family. Also pet friendly which was a PLUS! (however you would never know due to immaculate yard and clean interior!)
                                                                                                      • Submitted: Jan 3, 2017
                                                                                                      • Stayed: Dec 2016

                                                                                                      Good Choice

                                                                                                      4 of 5
                                                                                                      we were very pleased with the cottage. well equipped, clean, maintained and it served our needs well.
                                                                                                      • Submitted: Jan 2, 2017
                                                                                                      • Stayed: Dec 2016