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  • Showing 1-50 of 300+
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    • 3 BR
    • 3 BA
    • Sleeps 6
    Villa #3489038
    11
      Wonderful! 4.9/5
      (39 reviews)
      avg/night
      • 2 BR
      • 2 BA
      • Sleeps 6
      Villa #431377vb
      39
      Viewed 41 times in the last 48 hours
        Wonderful! 4.9/5
        (15 reviews)
        avg/night
        • 1 BR
        • 1 BA
        • Sleeps 2
        Villa #4087190
        15
        Viewed 58 times in the last 48 hours
          Excellent! 4.7/5
          (15 reviews)
          avg/night
          • 2 BR
          • 2 BA
          • Sleeps 5
          Villa #207472
          15
          Viewed 91 times in the last 48 hours
            Excellent! 4.6/5
            (36 reviews)
            avg/night
            • 1 BR
            • 1 BA
            • Sleeps 4
            Villa #3003070
            36
            Viewed 102 times in the last 48 hours
              Wonderful! 4.8/5
              (30 reviews)
              avg/night
              • 4 BR
              • 2 BA
              • Sleeps 8
              Villa #3934666
              30
              Viewed 135 times in the last 48 hours
                Excellent! 4.6/5
                (36 reviews)
                avg/night
                • 1 BR
                • 1 BA
                • Sleeps 4
                Villa #342421
                36
                Viewed 47 times in the last 48 hours
                  Exceptional! 5.0/5
                  (5 reviews)
                  avg/night
                  • 2 BR
                  • 2 BA
                  • Sleeps 6
                  Villa #846349vb
                  5
                  Viewed 47 times in the last 48 hours
                    Wonderful! 4.9/5
                    (39 reviews)
                    avg/night
                    • 2 BR
                    • 1 BA
                    • Sleeps 6
                    Villa #441464vb
                    39
                    Viewed 49 times in the last 48 hours
                      Exceptional! 5.0/5
                      (20 reviews)
                      avg/night
                      • 4 BR
                      • 2 BA
                      • Sleeps 12
                      Villa #3939239
                      20
                      Viewed 28 times in the last 48 hours
                        Wonderful! 4.9/5
                        (27 reviews)
                        avg/night
                        • 2 BR
                        • 1 BA
                        • Sleeps 4
                        Villa #460553vb
                        27
                        Viewed 38 times in the last 48 hours
                          Wonderful! 4.9/5
                          (39 reviews)
                          avg/night
                          • 2 BR
                          • 1 BA
                          • Sleeps 6
                          Villa #449380vb
                          39
                          Viewed 52 times in the last 48 hours
                            Wonderful! 4.8/5
                            (5 reviews)
                            $88
                            avg/night
                            • 3 BR
                            • 2 BA
                            • Sleeps 6
                            Villa #369470vb
                            5
                            Viewed 22 times in the last 48 hours
                              Wonderful! 4.8/5
                              (12 reviews)
                              avg/night
                              • 2 BR
                              • 2 BA
                              • Sleeps 4
                              Villa #499774vb
                              12
                              Viewed 21 times in the last 48 hours
                                avg/night
                                • 3 BR
                                • 2 BA
                                • Sleeps 8
                                Villa #4117118
                                4
                                Viewed 55 times in the last 48 hours
                                  Exceptional! 5.0/5
                                  (26 reviews)
                                  avg/night
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 5
                                  Villa #565341vb
                                  26
                                  Viewed 37 times in the last 48 hours
                                    Wonderful! 4.8/5
                                    (24 reviews)
                                    avg/night
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 4
                                    Villa #7108599
                                    24
                                    Viewed 72 times in the last 48 hours
                                      Wonderful! 4.9/5
                                      (22 reviews)
                                      avg/night
                                      • 2 BR
                                      • 1 BA
                                      • 1 HF BA
                                      • Sleeps 5
                                      Villa #558726vb
                                      22
                                      Viewed 54 times in the last 48 hours
                                        $88
                                        avg/night
                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 6
                                        Villa #8020459
                                        4
                                        Viewed 58 times in the last 48 hours
                                          Very Good! 4.0/5
                                          (5 reviews)
                                          $75
                                          avg/night
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 8
                                          Villa #504437vb
                                          5
                                          Viewed 26 times in the last 48 hours
                                            Excellent! 4.5/5
                                            (24 reviews)
                                            $82
                                            avg/night
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 5
                                            Villa #19396vb
                                            24
                                            Viewed 30 times in the last 48 hours
                                              Exceptional! 5.0/5
                                              (16 reviews)
                                              avg/night
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 6
                                              Villa #327339vb
                                              16
                                              Viewed 23 times in the last 48 hours
                                                Wonderful! 4.8/5
                                                (15 reviews)
                                                avg/night
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 6
                                                Villa #684372vb
                                                15
                                                Viewed 37 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (17 reviews)
                                                  avg/night
                                                  • 2 BR
                                                  • 1 BA
                                                  • 1 HF BA
                                                  • Sleeps 5
                                                  Villa #624083vb
                                                  17
                                                  Viewed 13 times in the last 48 hours
                                                    Excellent! 4.6/5
                                                    (16 reviews)
                                                    avg/night
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                    Villa #608793vb
                                                    16
                                                    Viewed 55 times in the last 48 hours
                                                      Exceptional! 5.0/5
                                                      (16 reviews)
                                                      avg/night
                                                      • 4 BR
                                                      • 2 BA
                                                      • Sleeps 8
                                                      Villa #219139
                                                      16
                                                      Viewed 23 times in the last 48 hours
                                                        Exceptional! 5.0/5
                                                        (16 reviews)
                                                        avg/night
                                                        • 4 BR
                                                        • 2 BA
                                                        • Sleeps 8
                                                        Villa #31171vb
                                                        16
                                                        Viewed 9 times in the last 48 hours
                                                          Exceptional! 5.0/5
                                                          (11 reviews)
                                                          avg/night
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 5
                                                          Villa #512153vb
                                                          11
                                                          Viewed 8 times in the last 48 hours
                                                            $81
                                                            avg/night
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 6
                                                            Villa #787188vb
                                                            1
                                                            Viewed 23 times in the last 48 hours
                                                              Wonderful! 4.9/5
                                                              (23 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              Villa #498588vb
                                                              23
                                                              Viewed 19 times in the last 48 hours
                                                                $72
                                                                avg/night
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 4
                                                                Villa #800611vb
                                                                Viewed 12 times in the last 48 hours
                                                                  • 3 BR
                                                                  • 1 BA
                                                                  • Sleeps 6
                                                                  Villa #8043470
                                                                  3
                                                                  Viewed 36 times in the last 48 hours
                                                                    Wonderful! 4.9/5
                                                                    (16 reviews)
                                                                    avg/night
                                                                    • 2 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    Villa #679204vb
                                                                    16
                                                                    Viewed 51 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (15 reviews)
                                                                      avg/night
                                                                      • 5 BR
                                                                      • 3 BA
                                                                      • Sleeps 10
                                                                      Villa #614352vb
                                                                      15
                                                                      Viewed 56 times in the last 48 hours
                                                                        Exceptional! 5.0/5
                                                                        (24 reviews)
                                                                        avg/night
                                                                        • 4 BR
                                                                        • 3 BA
                                                                        • Sleeps 10
                                                                        Villa #205209vb
                                                                        24
                                                                        Viewed 30 times in the last 48 hours
                                                                          Excellent! 4.6/5
                                                                          (35 reviews)
                                                                          avg/night
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 3
                                                                          Villa #439859vb
                                                                          35
                                                                          Viewed 14 times in the last 48 hours
                                                                            Exceptional! 5.0/5
                                                                            (22 reviews)
                                                                            avg/night
                                                                            • 2 BR
                                                                            • 2 BA
                                                                            • Sleeps 6
                                                                            Villa #7065vb
                                                                            22
                                                                            Viewed 60 times in the last 48 hours
                                                                              Exceptional! 5.0/5
                                                                              (28 reviews)
                                                                              avg/night
                                                                              • 6 BR
                                                                              • 4 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 14
                                                                              Villa #338161
                                                                              28
                                                                              Viewed 122 times in the last 48 hours
                                                                                avg/night
                                                                                • 4 BR
                                                                                • 2 BA
                                                                                • Sleeps 8
                                                                                Villa #875202vb
                                                                                3
                                                                                Viewed 19 times in the last 48 hours
                                                                                  avg/night
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                  Villa #824220vb
                                                                                  2
                                                                                  Viewed 6 times in the last 48 hours
                                                                                    Wonderful! 4.9/5
                                                                                    (9 reviews)
                                                                                    avg/night
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 6
                                                                                    Villa #935628
                                                                                    9
                                                                                    Viewed 18 times in the last 48 hours
                                                                                      Exceptional! 5.0/5
                                                                                      (5 reviews)
                                                                                      avg/night
                                                                                      • 4 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 8
                                                                                      Villa #655928vb
                                                                                      5
                                                                                      Viewed 21 times in the last 48 hours
                                                                                        Excellent! 4.7/5
                                                                                        (15 reviews)
                                                                                        avg/night
                                                                                        • 4 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 8
                                                                                        Villa #63274vb
                                                                                        15
                                                                                        Viewed 32 times in the last 48 hours
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 4
                                                                                          Villa #500376vb
                                                                                          2
                                                                                          Viewed 10 times in the last 48 hours
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 6
                                                                                            Villa #778155vb
                                                                                              Exceptional! 5.0/5
                                                                                              (26 reviews)
                                                                                              avg/night
                                                                                              • 4 BR
                                                                                              • 1 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 8
                                                                                              Villa #1169953
                                                                                              26
                                                                                              Viewed 20 times in the last 48 hours
                                                                                                Wonderful! 4.8/5
                                                                                                (15 reviews)
                                                                                                avg/night
                                                                                                • 2 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 6
                                                                                                Villa #959397
                                                                                                15
                                                                                                Viewed 46 times in the last 48 hours
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6
                                                                                                  Villa #907833vb
                                                                                                  Viewed 20 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (8 reviews)
                                                                                                    avg/night
                                                                                                    • 2 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 6
                                                                                                    Villa #574222vb
                                                                                                    8
                                                                                                    Viewed 42 times in the last 48 hours
                                                                                                      Excellent! 4.6/5
                                                                                                      (19 reviews)
                                                                                                      avg/night
                                                                                                      • 2 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 5
                                                                                                      Villa #106980
                                                                                                      19
                                                                                                      Viewed 10 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Osprey Reviews

                                                                                                      This bay front home is immaculate with sweeping views of bay.

                                                                                                      5 of 5
                                                                                                      The house was large enough to accomadote us comfortably. Very spacious. Wonderful pool with views of the bay. Close to downtown Sarasota and St Armand's. About a mile from airport. Owner was very accommodating and rapid responses with inquiries. Would highly recommend for large group or even small group. Thank you.
                                                                                                      • Submitted: Jan 20, 2017
                                                                                                      • Stayed: Jan 2017

                                                                                                      2016 Vacation

                                                                                                      5 of 5
                                                                                                      Villa was as described. Great location, short walk to beach using Acess 7. Magnificent shower. pebbled floor in shower is great on the soles of your feet and the shower head is to die for. Adequate room for our clothes (mine and grown daughter). All things provided for in the villa were very useful. We found the WiFi very slow and the TV volume would change continuously by itself. This was on the TV in living area. Did not use the bedroom TV. Overall, I would go back in a heartbeat. As noted, walking distance to the Village. The Key also has free "shuttle" service by a couple of businesses. One uses a regular van and the other is a 5 passenger golf cart. Payment is tips only. Will take you anywhere on the key and pick you up for home. Also has 2 fare based regular taxi's that will go off the key. Property manager is very nice and very easy to work with. Recommend either of the 2 villas or the house behind.
                                                                                                      • Submitted: Jan 8, 2017
                                                                                                      • Stayed: Dec 2016

                                                                                                      Lovely villa

                                                                                                      5 of 5
                                                                                                      Spent a wonderful Christmas holiday in Villa B. The villa was in immaculate condition and such a lovely space. Can't beat the location either. Would definitely stay here again!
                                                                                                      • Submitted: Dec 27, 2016
                                                                                                      • Stayed: Dec 2016