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
Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Osprey: Condos, Houses & More (300+)

  • 1 - 50 of 300+
Additional fees apply. Taxes may be added.
    Wonderful! 4.9/5
    (30 reviews)
    avg/night
    • 3 BR
    • 2 BA
    • Sleeps 8
    30
      • 3 BR
      • 3 BA
      • Sleeps 6
      5
        • 4 BR
        • 3 BA
        • 1 HF BA
        • Sleeps 10
          • 3 BR
          • 3 BA
          • Sleeps 10
          2 Reviews
            • 2 BR
            • 2 BA
            • Sleeps 6
              • 3 BR
              • 2 BA
              • 1 HF BA
              • Sleeps 6
              3
                Wonderful! 4.8/5
                (17 reviews)
                avg/night
                • 3 BR
                • 2 BA
                • Sleeps 6
                17
                  • 3 BR
                  • 2 BA
                  • Sleeps 6
                    • 2 BR
                    • 2 BA
                    • Sleeps 4
                      • 3 BR
                      • 3 BA
                      • Sleeps 6
                      11
                        • 2 BR
                        • 2 BA
                        • Sleeps 6
                        1 Review
                          • 4 BR
                          • 4 BA
                          • Sleeps 12
                          1 Review
                            • 3 BR
                            • 2 BA
                            • Sleeps 6
                              Wonderful! 4.8/5
                              (17 reviews)
                              avg/night
                              • 3 BR
                              • 2 BA
                              • Sleeps 6
                              17
                                • 4 BR
                                • 2 BA
                                • Sleeps 7
                                4
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 8
                                    • 3 BR
                                    • 4 BA
                                    • Sleeps 6
                                    1 Review
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 4
                                        • 2 BR
                                        • 1 BA
                                        • 1 HF BA
                                        • Sleeps 6
                                        17
                                          Excellent! 4.7/5
                                          (9 reviews)
                                          avg/night
                                          • 2 BR
                                          • 2 BA
                                          • 1 HF BA
                                          • Sleeps 4
                                          9
                                            • 1 BR
                                            • 1 BA
                                            • Sleeps 2
                                            8
                                              Exceptional! 5.0/5
                                              (11 reviews)
                                              avg/night
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 6
                                              11
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 6
                                                1 Review
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 8
                                                  4
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 2
                                                    19
                                                      • 2 BR
                                                      • 1 BA
                                                      • Sleeps 4
                                                      14
                                                        • 2 BR
                                                        • 2 BA
                                                        • Sleeps 4
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 4
                                                            Exceptional! 5.0/5
                                                            (11 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 6
                                                            11
                                                              • 2 BR
                                                              • 14 BA
                                                              • 1 HF BA
                                                              • Sleeps 6
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 6
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 4
                                                                  3
                                                                    • 4 BR
                                                                    • 4 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 10
                                                                    20
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 6
                                                                      12
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 7
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 5
                                                                          20
                                                                            • 2 BR
                                                                            • 2 BA
                                                                            • Sleeps 4
                                                                            3
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 7
                                                                                Wonderful! 4.9/5
                                                                                (37 reviews)
                                                                                $71
                                                                                avg/night
                                                                                • 2 BR
                                                                                • 2 BA
                                                                                • Sleeps 6
                                                                                37
                                                                                  • 2 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                    Exceptional! 5.0/5
                                                                                    (16 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 4
                                                                                    16
                                                                                      Excellent! 4.7/5
                                                                                      (21 reviews)
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 4
                                                                                      21
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 3
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                          8
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 4
                                                                                            2 Reviews
                                                                                              Excellent! 4.7/5
                                                                                              (15 reviews)
                                                                                              avg/night
                                                                                              • 4 BR
                                                                                              • Sleeps 8
                                                                                              15
                                                                                                Wonderful! 4.8/5
                                                                                                (13 reviews)
                                                                                                avg/night
                                                                                                • 2 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 4
                                                                                                13
                                                                                                  • 2 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6
                                                                                                  15
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 6
                                                                                                    4
                                                                                                      • 2 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 4
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Osprey Reviews

                                                                                                      Perfect location at the perfect price

                                                                                                      5 of 5
                                                                                                      We arrived right after hurricane Hermine paid a visit to the area. Property was in perfect shape, including the pool. The villa is exactly as shown in the pictures. It was clean, very bright and the pool, deck and covered patio are perfect for an outside dinner after watching a beautiful sunset at the beach. Owner Linda promptly communicated with us during the transaction and prior to arrival. She allowed us to bring our small dog (who does not shed and is very well house trained ). We live in South Florida so for us is the perfect place for a long weekend escape. Definitively we will return.
                                                                                                      • Submitted: Sep 6, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      Weekend Escape

                                                                                                      5 of 5
                                                                                                      Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This place was perfect weekend getaway. Location was great, the beach was a hop skip and a jump away. The kitchen had everything we needed to stay in and cook dinner. Getting up each morning and sitting on the porch enjoying coffee and a book was a wonderful treat ?? I will be back soon
                                                                                                      • Submitted: Aug 30, 2016
                                                                                                      • Stayed: Aug 2016

                                                                                                      quiet, vintage hideaway

                                                                                                      5 of 5
                                                                                                      I had some business to attend to in Sarasota, and this quiet, modest retreat allowed me the peace of mind to do what i had to do . .. Jane was welcoming at my arrival, and immediately responsive when there were plumbing issues . .. .after some days of rain, i was happy to be close to Siesta Key . . . i can easily recommend this listing to anyone who values peace and privacy . .. . Reva W.
                                                                                                      • Submitted: Aug 25, 2016
                                                                                                      • Stayed: Aug 2016