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1,418 Holiday homes

    24

    Holiday condo in Osprey

    Florida / Osprey

    1 4 min stay varies

    • 1 bedroom
    • sleeps 4
    • min stay varies
    • Swimming pool
    • Child friendly
    • Air conditioning

    from £98 / night

    £683 / week

    Book View

    Responds fast!
    avg. 19 minutes

    from £98 / night

      24

      Holiday apartment in Osprey

      Florida / Osprey

      2 4 min stay varies

      • 2 bedrooms
      • sleeps 4
      • min stay varies
      • Swimming pool
      • Child friendly
      • Air conditioning

      from £126 / night

      £882 / week

      Book View

      Responds fast!
      avg. 19 minutes

      from £126 / night

        29

        Villa accommodation in Osprey with golf nearby

        Florida / Osprey

        2 6 1 night min

        • 2 bedrooms
        • sleeps 6
        • 1 night min
        • Nearest beach 7 km
        • Swimming pool
        • Child friendly

        from £106 / night

        £739 / week

        Book View

        from £106 / night

          24

          Osprey holiday condo rental

          Florida / Osprey

          3 6 min stay varies

          • 3 bedrooms
          • sleeps 6
          • min stay varies
          • Child friendly
          • Air conditioning
          • Pet friendly

          from £250 / night

          £2,134 / week

          Book View

          from £250 / night

            14

            Holiday apartment with shared pool in Osprey

            Florida / Osprey

            1 4 min stay varies

            • 1 bedroom
            • sleeps 4
            • min stay varies
            • Swimming pool
            • Child friendly
            • Car not necessary

            from £128 / night

            £832 - £1,198 / week

            Book View

            Responds fast!
            avg. 3 hours 35 minutes

            from £128 / night

            (2) Very Good 

              17

              Holiday home in Osprey

              Florida / Osprey

              3 5 3 nights min

              • 3 bedrooms
              • sleeps 5
              • 3 nights min
              • Swimming pool
              • Child friendly
              • Air conditioning

              from £156 / night

              £975 / week

              Book View

              from £156 / night

                25

                Holiday condo in Osprey

                Florida / Osprey

                2 4 min stay varies

                • 2 bedrooms
                • sleeps 4
                • min stay varies
                • Child friendly

                from £85 / night

                £590 / week

                Book View

                from £85 / night

                  18

                  Holiday condo in Osprey

                  Florida / Osprey

                  1 4 30 nights min

                  • 1 bedroom
                  • sleeps 4
                  • 30 nights min
                  • Child friendly

                  from £61 / night

                  £422 / week

                  Book View

                  from £61 / night

                    16

                    Holiday home in Osprey

                    Florida / Osprey

                    3 6 min stay varies

                    • 3 bedrooms
                    • sleeps 6
                    • min stay varies
                    • Swimming pool
                    • Child friendly
                    • Air conditioning

                    from £67 / night

                    £466 / week

                    Book View

                    from £67 / night

                      32

                      Holiday home in Osprey

                      Florida / Osprey

                      3 7 min stay varies

                      • 3 bedrooms
                      • sleeps 7
                      • min stay varies
                      • Child friendly

                      from £111 / night

                      £776 / week

                      Book View

                      from £111 / night

                      (2) Excellent 

                        57

                        Holiday condo with golf nearby in Osprey

                        Florida / Osprey

                        2 4 30 nights min

                        • 2 bedrooms
                        • sleeps 4
                        • 30 nights min
                        • Swimming pool
                        • Child friendly
                        • Air conditioning

                        from £54 / night

                        £373 / week

                        Book View

                        from £54 / night

                        Great rentals within 20 miles that match your search

                        Distance approx 16.7 miles from Osprey

                        (2) Excellent 

                          12

                          Home rental in Sarasota with indoor pool, golf nearby

                          Southwest Gulf Coast / Sarasota

                          4 8 7 nights min

                          • 4 bedrooms
                          • sleeps 8
                          • 7 nights min
                          • Beach / lakeside relaxation
                          • Swimming pool
                          • Child friendly

                          from £100 / night

                          £695 - £1,457 / week

                          Book View

                          from £100 / night

                          Distance approx 2.03 miles from Osprey Show on Map

                          (30) Excellent 

                            28

                            Siesta Key holiday condo rental

                            Florida / Siesta Key

                            2 5 7 nights min

                            • 2 bedrooms
                            • sleeps 5
                            • 7 nights min
                            • Beach / lakeside relaxation
                            • Nearest beach 0.01 km
                            • Swimming pool

                            from £317 / night

                            £2,217 / week

                            Book View

                            Responds fast!
                            avg. 30 minutes

                            from £317 / night

                            Distance approx 5.11 miles from Osprey

                            (1) Very Good 

                              12

                              Villa rental in Nokomis

                              Florida / Nokomis

                              1 3 3 nights min

                              • 1 bedroom
                              • sleeps 3
                              • 3 nights min
                              • Child friendly
                              • Air conditioning
                              • Pet friendly

                              from £125 / night

                              £709 - £771 / week

                              Book View

                              from £125 / night

                              Distance approx 18.61 miles from Osprey

                                13

                                Holiday home in Manasota Key

                                Southwest Gulf Coast / Manasota Key

                                2 4 7 nights min

                                • 2 bedrooms
                                • sleeps 4
                                • 7 nights min
                                • Child friendly
                                • Car not necessary
                                • Air conditioning

                                from £288 / night

                                £1,862 / week

                                Book View

                                from £288 / night

                                Distance approx 9.17 miles from Osprey

                                (5) Excellent 

                                  21

                                  Lido Key holiday home rental

                                  Sarasota / Lido Key

                                  2 6 min stay varies

                                  • 2 bedrooms
                                  • sleeps 6
                                  • min stay varies
                                  • Nearest beach 0.2 km
                                  • Child friendly
                                  • Car not necessary

                                  from £89 / night

                                  £1,241 / week

                                  Book View

                                  Responds fast!
                                  avg. 1 hour 35 minutes

                                  from £89 / night

                                  Distance approx 13.63 miles from Osprey

                                    37

                                    Venice holiday home rental

                                    Southwest Gulf Coast / Venice

                                    1 3 90 nights min

                                    • 1 bedroom
                                    • sleeps 3
                                    • 90 nights min
                                    • Child friendly

                                    from £93 / night

                                    £559 / week

                                    Book View

                                    from £93 / night

                                    Distance approx 18.43 miles from Osprey

                                      21

                                      Englewood holiday apartment rental

                                      Southwest Gulf Coast / Englewood

                                      1 3 1 night min

                                      • 1 bedroom
                                      • sleeps 3
                                      • 1 night min
                                      • Child friendly
                                      • Air conditioning
                                      • Private garden

                                      from £89 / night

                                      £577 - £710 / week

                                      Book View

                                      Responds fast!
                                      avg. 2 hours 8 minutes

                                      from £89 / night

                                      Distance approx 16.51 miles from Osprey

                                      (1) Excellent 

                                        37

                                        Holiday home in Bradenton

                                        Southwest Gulf Coast / Bradenton

                                        2 6 4 nights min

                                        • 2 bedrooms
                                        • sleeps 6
                                        • 4 nights min
                                        • Child friendly
                                        • Pet friendly

                                        from £88 / night

                                        £615 / week

                                        Book View

                                        Responds fast!
                                        avg. 1 hour 37 minutes

                                        from £88 / night

                                        Distance approx 5.11 miles from Osprey

                                          12

                                          Nokomis holiday villa rental

                                          Florida / Nokomis

                                          1 3 3 nights min

                                          • 1 bedroom
                                          • sleeps 3
                                          • 3 nights min
                                          • Child friendly
                                          • Air conditioning
                                          • Pet friendly

                                          from £88 / night

                                          £687 - £749 / week

                                          Book View

                                          from £88 / night

                                          Distance approx 4.85 miles from Osprey Show on Map

                                          (18) Very Good 

                                            24

                                            Condo rental in Siesta Key

                                            Florida / Siesta Key

                                            2 6 7 nights min

                                            • 2 bedrooms
                                            • sleeps 6
                                            • 7 nights min
                                            • Beach / lakeside relaxation
                                            • Swimming pool
                                            • Child friendly

                                            from £153 / night

                                            £1,131 - £1,662 / week

                                            Book View

                                            Responds fast!
                                            avg. 1 hour 18 minutes

                                            from £153 / night

                                            Distance approx 19.35 miles from Osprey

                                            (12) Excellent 

                                              20

                                              Holiday apartment with golf nearby in Bradenton

                                              Southwest Gulf Coast / Bradenton

                                              2 6 min stay varies

                                              • 2 bedrooms
                                              • sleeps 6
                                              • min stay varies
                                              • Beach / lakeside relaxation
                                              • Nearest beach 10 km
                                              • Swimming pool

                                              from £107 / night

                                              £531 - £860 / week

                                              Book View

                                              Responds fast!
                                              avg. 2 hours 40 minutes

                                              from £107 / night

                                              Distance approx 9.27 miles from Osprey

                                              (18) Excellent 

                                                44

                                                Holiday home in Sarasota

                                                Southwest Gulf Coast / Sarasota

                                                2 4 min stay varies

                                                • 2 bedrooms
                                                • sleeps 4
                                                • min stay varies
                                                • Nearest beach 6 km
                                                • Child friendly
                                                • Air conditioning

                                                from £111 / night

                                                £776 / week

                                                Book View

                                                Responds fast!
                                                avg. 45 minutes

                                                from £111 / night

                                                Distance approx 19.43 miles from Osprey

                                                (3) Very Good 

                                                  50

                                                  Condo rental in Bradenton with golf nearby

                                                  Southwest Gulf Coast / Bradenton

                                                  2 4 min stay varies

                                                  • 2 bedrooms
                                                  • sleeps 4
                                                  • min stay varies
                                                  • Beach / lakeside relaxation
                                                  • Nearest beach 10 km
                                                  • Swimming pool

                                                  from £107 / night

                                                  £714 - £993 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 45 minutes

                                                  from £107 / night

                                                  Distance approx 4.15 miles from Osprey Show on Map

                                                  (4) Very Good 

                                                  Certificate of Excellence

                                                    22

                                                    Condo rental in Siesta Key

                                                    Florida / Siesta Key

                                                    1 4 min stay varies

                                                    • 1 bedroom
                                                    • sleeps 4
                                                    • min stay varies
                                                    • Child friendly
                                                    • Air conditioning

                                                    Certificate of Excellence

                                                    from £115 / night

                                                    £801 / week

                                                    Book View

                                                    from £115 / night

                                                    Distance approx 5.98 miles from Osprey

                                                      7

                                                      Holiday townhouse rental

                                                      Florida / Siesta Key

                                                      2 6 7 nights min

                                                      • 2 bedrooms
                                                      • sleeps 6
                                                      • 7 nights min
                                                      • Swimming pool
                                                      • Child friendly
                                                      • Car not necessary

                                                      from £176 / night

                                                      £1,232 - £1,717 / week

                                                      Book View

                                                      from £176 / night

                                                      Distance approx 19.38 miles from Osprey

                                                      (5) Excellent 

                                                      Certificate of Excellence

                                                        43

                                                        Bradenton holiday apartment rental

                                                        Southwest Gulf Coast / Bradenton

                                                        2 4 min stay varies

                                                        • 2 bedrooms
                                                        • sleeps 4
                                                        • min stay varies
                                                        • Beach / lakeside relaxation
                                                        • Nearest beach 11 km
                                                        • Swimming pool

                                                        Certificate of Excellence

                                                        from £88 / night

                                                        £540 - £975 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 3 hours 2 minutes

                                                        from £88 / night

                                                        Distance approx 4.94 miles from Osprey Show on Map

                                                        (3) Excellent 

                                                          20

                                                          Holiday home in Sarasota

                                                          Southwest Gulf Coast / Sarasota

                                                          2 6 min stay varies

                                                          • 2 bedrooms
                                                          • sleeps 6
                                                          • min stay varies
                                                          • Child friendly
                                                          • Air conditioning

                                                          from £88 / night

                                                          £615 / week

                                                          Book View

                                                          Responds fast!
                                                          avg. 1 hour 19 minutes

                                                          from £88 / night

                                                          Distance approx 7.12 miles from Osprey

                                                            28

                                                            Siesta Key holiday home rental

                                                            Florida / Siesta Key

                                                            3 8 7 nights min

                                                            • 3 bedrooms
                                                            • sleeps 8
                                                            • 7 nights min
                                                            • Child friendly

                                                            from £417 / night

                                                            £2,917 / week

                                                            Book View

                                                            from £417 / night

                                                            Distance approx 6.36 miles from Osprey

                                                              39

                                                              Siesta Key holiday home rental

                                                              Florida / Siesta Key

                                                              4 12 7 nights min

                                                              • 4 bedrooms
                                                              • sleeps 12
                                                              • 7 nights min
                                                              • Swimming pool
                                                              • Child friendly

                                                              from £460 / night

                                                              £3,221 / week

                                                              Book View

                                                              from £460 / night

                                                              Distance approx 6.85 miles from Osprey

                                                              (17) Very Good 

                                                                49

                                                                Siesta Key holiday home rental

                                                                Florida / Siesta Key

                                                                3 10 3 nights min

                                                                • 3 bedrooms
                                                                • sleeps 10
                                                                • 3 nights min
                                                                • Beach / lakeside relaxation
                                                                • Nearest beach 0.1 km
                                                                • Child friendly

                                                                from £88 / night

                                                                £615 / week

                                                                Book View

                                                                Responds fast!
                                                                avg. 2 hours 23 minutes

                                                                from £88 / night

                                                                Distance approx 4.81 miles from Osprey Show on Map

                                                                  24

                                                                  Holiday condo with golf nearby in Siesta Key

                                                                  Florida / Siesta Key

                                                                  3 6 min stay varies

                                                                  • 3 bedrooms
                                                                  • sleeps 6
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Child friendly
                                                                  • Air conditioning

                                                                  from £123 / night

                                                                  £857 - £1,627 / week

                                                                  Book View

                                                                  from £123 / night

                                                                  Distance approx 17.84 miles from Osprey

                                                                    11

                                                                    Longboat Key holiday condo rental

                                                                    Florida / Longboat Key

                                                                    2 6 7 nights min

                                                                    • 2 bedrooms
                                                                    • sleeps 6
                                                                    • 7 nights min
                                                                    • Swimming pool
                                                                    • Child friendly
                                                                    • Air conditioning

                                                                    from £228 / night

                                                                    £1,596 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 35 minutes

                                                                    from £228 / night

                                                                    Distance approx 2.81 miles from Osprey Show on Map

                                                                      19

                                                                      Casey Key holiday villa rental

                                                                      Florida / Casey Key

                                                                      3 8 min stay varies

                                                                      • 3 bedrooms
                                                                      • sleeps 8
                                                                      • min stay varies
                                                                      • Child friendly

                                                                      from £151 / night

                                                                      £975 - £1,108 / week

                                                                      Book View

                                                                      from £151 / night

                                                                      Distance approx 7 miles from Osprey

                                                                        20

                                                                        Holiday apartment in Siesta Key

                                                                        Florida / Siesta Key

                                                                        2 6 7 nights min

                                                                        • 2 bedrooms
                                                                        • sleeps 6
                                                                        • 7 nights min
                                                                        • Child friendly
                                                                        • Pet friendly

                                                                        from £186 / night

                                                                        £1,297 / week

                                                                        Book View

                                                                        from £186 / night

                                                                        Distance approx 16.21 miles from Osprey

                                                                          10

                                                                          Holiday cottage in Braden River

                                                                          Florida / Braden River

                                                                          1 4 2 nights min

                                                                          • 1 bedroom
                                                                          • sleeps 4
                                                                          • 2 nights min
                                                                          • Nearest beach 11 km
                                                                          • Child friendly
                                                                          • Air conditioning

                                                                          from £40 / night

                                                                          £280 / week

                                                                          Book View

                                                                          Responds fast!
                                                                          avg. 3 hours 49 minutes

                                                                          from £40 / night

                                                                          Distance approx 18.67 miles from Osprey

                                                                            17

                                                                            Holiday apartment with golf nearby in Oneco

                                                                            Florida / Oneco

                                                                            1 4 3 nights min

                                                                            • 1 bedroom
                                                                            • sleeps 4
                                                                            • 3 nights min
                                                                            • Child friendly
                                                                            • Air conditioning
                                                                            • Private garden

                                                                            from £85 / night

                                                                            £577 - £665 / week

                                                                            Book View

                                                                            from £85 / night

                                                                            Distance approx 2.82 miles from Osprey Show on Map

                                                                              22

                                                                              Villa accommodation in Sarasota

                                                                              Southwest Gulf Coast / Sarasota

                                                                              2 6 7 nights min

                                                                              • 2 bedrooms
                                                                              • sleeps 6
                                                                              • 7 nights min
                                                                              • Swimming pool
                                                                              • Child friendly
                                                                              • Air conditioning

                                                                              from £212 / night

                                                                              £1,483 - £1,670 / week

                                                                              Book View

                                                                              Responds fast!
                                                                              avg. 2 hours 37 minutes

                                                                              from £212 / night

                                                                              Distance approx 6.03 miles from Osprey

                                                                                20

                                                                                Holiday condo with shared pool in Siesta Key

                                                                                Florida / Siesta Key

                                                                                2 6 min stay varies

                                                                                • 2 bedrooms
                                                                                • sleeps 6
                                                                                • min stay varies
                                                                                • Swimming pool
                                                                                • Child friendly
                                                                                • Car not necessary

                                                                                from £176 / night

                                                                                £1,229 - £1,800 / week

                                                                                Book View

                                                                                Responds fast!
                                                                                avg. 3 hours 35 minutes

                                                                                from £176 / night

                                                                                Distance approx 2.44 miles from Osprey Show on Map

                                                                                  24

                                                                                  Holiday condo with shared pool in Sarasota

                                                                                  Southwest Gulf Coast / Sarasota

                                                                                  2 6 30 nights min

                                                                                  • 2 bedrooms
                                                                                  • sleeps 6
                                                                                  • 30 nights min
                                                                                  • Swimming pool
                                                                                  • Child friendly
                                                                                  • Air conditioning

                                                                                  from £89 / night

                                                                                  £621 / week

                                                                                  Book View

                                                                                  from £89 / night

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