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1,760 Houses

    24

    NEW! Siesta Key Condo w/Pool-Walk to Turtle Beach!

    Florida / Osprey

    Osprey condo

    1 4 min stay varies

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

    Price per night from

    $126

    Responds fast!
    avg. 9 minutes

    Price per night from

    $126

      24

      Sarasota Condo w/Deck - 1/2 mile to Turtle Beach!

      Florida / Osprey

      Osprey apartment

      2 4 min stay varies

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

      Price per night from

      $163

      Responds fast!
      avg. 9 minutes

      Price per night from

      $163

        29

        LUX VILLAs close to sparkling Siesta Key Beach.

        Florida / Osprey

        Osprey villa

        2 6 1 night min

        • 2 bedrooms
        • sleeps 6
        • 1 night min
        • Nearest beach 7 mi
        • Swimming pool
        • Child Friendly

        Price per night from

        $137

        Price per night from

        $137

          24

          Spacious Sarasota Waterfront Pool Home with Dock - Amazing Sunsets Included

          Florida / Osprey

          Osprey condo

          3 6 min stay varies

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

          Price per night from

          $323

          Price per night from

          $323

            24

            Sunny 3BR Oasis w/ New Appliances & Furnishings—Near Coast, Dining

            Florida / Osprey

            Osprey house

            3 6 min stay varies

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

            Price per night from

            $98

            Price per night from

            $98

            (2) Very Good 

              17

              Pet friendly paradise with heated pool close to Sarasota-Osprey-Nokomis-Venice

              Florida / Osprey

              Osprey house

              3 5 3 nights min

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

              Price per night from

              $201

              Price per night from

              $201

                14

                Fisherman's Cove - A207

                Florida / Osprey

                Osprey apartment

                1 4 min stay varies

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

                Price per night from

                $165

                Price per night from

                $165

                  25

                  Osprey 01

                  Florida / Osprey

                  Osprey condo

                  2 4 min stay varies

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

                  Price per night from

                  $187

                  Price per night from

                  $187

                    32

                    Sarasota 38

                    Florida / Osprey

                    Osprey house

                    3 7 min stay varies

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

                    Price per night from

                    $157

                    Price per night from

                    $157

                      19

                      Bay Tree 407

                      Florida / Osprey

                      Osprey house

                      2 6 min stay varies

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

                      Price per night from

                      $194

                      Price per night from

                      $194

                        18

                        Condo with breathtaking View of Sarasota Bay

                        Florida / Osprey

                        Osprey condo

                        1 4 30 nights min

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

                        Price per night from

                        $78

                        Price per night from

                        $78

                        (2) Excellent 

                          57

                          2 BR / 2 BA Condo in Stoneybrook Golf & County Club - Sarasota & Siesta Key

                          Florida / Osprey

                          Osprey condo

                          2 4 30 nights min

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

                          Price per night from

                          $69

                          Price per night from

                          $69

                            16

                            Beautiful South Sarasota Bay Home in Harbor Front Community

                            Florida / Osprey

                            Osprey house

                            3 6 min stay varies

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

                            Price per night from

                            $86

                            Price per night from

                            $86

                              15

                              CKBH (Casey Key Beach House)

                              Florida / Osprey

                              Osprey house

                              3 6 7 nights min

                              • 3 bedrooms
                              • sleeps 6
                              • 7 nights min
                              • Swimming pool
                              • Child Friendly
                              • Air conditioning

                              Price per night from

                              $581

                              Price per night from

                              $581

                              Great rentals within 20 miles that match your search

                              Distance approx 5.88 km from Osprey

                              (18) Very Good 

                                21

                                Luxurious 2 BR Condo - Short Walk to Siesta Beach

                                Florida / Siesta Key

                                Siesta Key apartment

                                2 6 14 nights min

                                • 2 bedrooms
                                • sleeps 6
                                • 14 nights min
                                • Beach / lakeside relaxation
                                • Nearest beach 0.2 mi
                                • Swimming pool
                                “a fine 2 weeks in Siesta” charming property, that was comfortable for four. The unit was very clean and fresh upon arrival. The neighbours were friendly and the overall property well kept. Siesta Key is a quiet community with usual shopping amenitie
                                …see more

                                Price per night from

                                $129

                                Responds fast!
                                avg. 3 hours 7 minutes

                                Price per night from

                                $129

                                Distance approx 12.65 km from Osprey

                                  18

                                  Amazing View - 2 Bed 2 Bath Condo on Golf Course

                                  Southwest Gulf Coast / Venice

                                  Venice condo

                                  2 4 5 nights min

                                  • 2 bedrooms
                                  • sleeps 4
                                  • 5 nights min
                                  • Swimming pool
                                  • Child Friendly
                                  • Air conditioning

                                  Price per night from

                                  $172

                                  Price per night from

                                  $172

                                  Distance approx 5.11 km from Osprey

                                    18

                                    Casey Key 2-Bed Dockside Penthouse

                                    Florida / Nokomis

                                    Nokomis penthouse

                                    2 6 3 nights min

                                    • 2 bedrooms
                                    • sleeps 6
                                    • 3 nights min
                                    • Child Friendly
                                    • Pet Friendly

                                    Price per night from

                                    $178

                                    Price per night from

                                    $178

                                    Distance approx 19.79 km from Osprey

                                    (1) Excellent 

                                      32

                                      Water Lover's Delight! 3/2 fully renovated home with boat ramp & davits.

                                      Southwest Gulf Coast / Manasota Key

                                      Manasota Key house

                                      3 6 7 nights min

                                      • 3 bedrooms
                                      • sleeps 6
                                      • 7 nights min
                                      • Child Friendly
                                      • Air conditioning
                                      • Private garden

                                      Price per night from

                                      $164

                                      Price per night from

                                      $164

                                      Distance approx 19.39 km from Osprey

                                        24

                                        SHOREWALK VACATION VILLA

                                        Southwest Gulf Coast / Bradenton

                                        Bradenton apartment

                                        2 4 5 nights min

                                        • 2 bedrooms
                                        • sleeps 4
                                        • 5 nights min
                                        • Beach / lakeside relaxation
                                        • Nearest beach 15 mi
                                        • Swimming pool

                                        Price per night from

                                        $144

                                        Price per night from

                                        $144

                                        Distance approx 11.76 km from Osprey

                                          18

                                          Venice paradise house

                                          Southwest Gulf Coast / Venice

                                          Venice house

                                          3 7 5 nights min

                                          • 3 bedrooms
                                          • sleeps 7
                                          • 5 nights min
                                          • Child Friendly
                                          • Air conditioning
                                          • Private garden

                                          Price per night from

                                          $205

                                          Price per night from

                                          $205

                                          Distance approx 17.78 km from Osprey

                                          (1) Very Good 

                                            21

                                            Quite newer home minutes from shopping and beaches

                                            Florida / North Port

                                            North Port house

                                            3 6 2 nights min

                                            • 3 bedrooms
                                            • sleeps 6
                                            • 2 nights min
                                            • Child Friendly
                                            • Air conditioning
                                            • Private garden

                                            Price per night from

                                            $401

                                            Price per night from

                                            $401

                                            Distance approx 7.54 km from Osprey

                                              24

                                              Dog Friendly Heated Pool Home Close to Beaches & Town

                                              Southwest Gulf Coast / Sarasota

                                              Sarasota house

                                              3 6 min stay varies

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

                                              Price per night from

                                              $172

                                              Responds fast!
                                              avg. 1 hour 57 minutes

                                              Price per night from

                                              $172

                                              Distance approx 6.95 km from Osprey

                                                10

                                                2 Bed, 2Bath, 6Sleeps.

                                                Southwest Gulf Coast / Venice

                                                Venice house

                                                2 6 30 nights min

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

                                                Price per night from

                                                $83

                                                Responds fast!
                                                avg. 40 minutes

                                                Price per night from

                                                $83

                                                Distance approx 16.48 km from Osprey

                                                  24

                                                  Spacious Englewood House w/Deck - On The Beach!

                                                  Southwest Gulf Coast / Englewood

                                                  Englewood house

                                                  5 12 min stay varies

                                                  • 5 bedrooms
                                                  • sleeps 12
                                                  • min stay varies
                                                  • Child Friendly
                                                  • Air conditioning

                                                  Price per night from

                                                  $567

                                                  Responds fast!
                                                  avg. 10 minutes

                                                  Price per night from

                                                  $567

                                                  Distance approx 5.03 km from Osprey Show on Map

                                                    9

                                                    Moonmist Villa

                                                    Southwest Gulf Coast / Sarasota

                                                    Sarasota villa

                                                    2 5 7 nights min

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

                                                    Price per night from

                                                    $213

                                                    Price per night from

                                                    $213

                                                    Distance approx 4.77 km from Osprey Show on Map

                                                      18

                                                      Chic and Relaxing Ground Floor Condo, with Gulf Beach Access

                                                      Florida / Siesta Key

                                                      Siesta Key condo

                                                      2 6 7 nights min

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

                                                      Price per night from

                                                      $128

                                                      Price per night from

                                                      $128

                                                      Distance approx 18.11 km from Osprey

                                                        15

                                                        Peaceful, Private, Paradise in Englewood. House with heated pool

                                                        Southwest Gulf Coast / Englewood

                                                        Englewood house

                                                        3 6 7 nights min

                                                        • 3 bedrooms
                                                        • sleeps 6
                                                        • 7 nights min
                                                        • Child Friendly
                                                        • Pet Friendly

                                                        Price per night from

                                                        $258

                                                        Price per night from

                                                        $258

                                                        Distance approx 5.12 km from Osprey Show on Map

                                                          14

                                                          CANCELLATION OPENS MARCH 28th ON! HURRY BEFORE IT'S GONE

                                                          Florida / Siesta Key

                                                          Siesta Key condo

                                                          2 6 min stay varies

                                                          • 2 bedrooms
                                                          • sleeps 6
                                                          • min stay varies
                                                          • Swimming pool
                                                          • Child Friendly
                                                          • Air conditioning

                                                          Price per night from

                                                          $166

                                                          Price per night from

                                                          $166

                                                          Distance approx 4.15 km from Osprey Show on Map

                                                            24

                                                            NEW! Siesta Key Condo - Steps to Crescent Beach!

                                                            Florida / Gulf Gate Branch

                                                            Gulf Gate Branch condo

                                                            1 4 2 nights min

                                                            • 1 bedroom
                                                            • sleeps 4
                                                            • 2 nights min
                                                            • Child Friendly
                                                            • Air conditioning

                                                            Price per night from

                                                            $258

                                                            Responds fast!
                                                            avg. 56 minutes

                                                            Price per night from

                                                            $258

                                                            Distance approx 3.51 km from Osprey Show on Map

                                                              26

                                                              Bright 2 bedroom home 10 minutes to Siesta Key - Lots of restaurants nearby

                                                              Florida / Gulf Gate Branch

                                                              Gulf Gate Branch house

                                                              2 4 min stay varies

                                                              • 2 bedrooms
                                                              • sleeps 4
                                                              • min stay varies
                                                              • Child Friendly
                                                              • Air conditioning

                                                              Price per night from

                                                              $102

                                                              Responds fast!
                                                              avg. 3 hours 55 minutes

                                                              Price per night from

                                                              $102

                                                              Distance approx 6.85 km from Osprey

                                                              (17) Very Good 

                                                                49

                                                                Top in Siesta Village at Best Beaches, Food & Entertainment! - Casa Van Lopik(J)

                                                                Florida / Siesta Key

                                                                Siesta Key house

                                                                3 10 3 nights min

                                                                • 3 bedrooms
                                                                • sleeps 10
                                                                • 3 nights min
                                                                • Beach / lakeside relaxation
                                                                • Nearest beach 0.1 mi
                                                                • Child Friendly
                                                                “Location, Location, Location!” Great house. Just as pictured and described. Dan and Jon are super-easy hosts. I like the little things - that the house is set up and fully ready. Abundance of supplies and towels, even beach chairs await! This having
                                                                …see more

                                                                Price per night from

                                                                $264

                                                                Responds fast!
                                                                avg. 1 hour 54 minutes

                                                                Price per night from

                                                                $264

                                                                Distance approx 7.32 km from Osprey

                                                                  22

                                                                  Sarasota golf course home/heated swimming pool

                                                                  Southwest Gulf Coast / Sarasota

                                                                  Sarasota house

                                                                  2 6 min stay varies

                                                                  • 2 bedrooms
                                                                  • sleeps 6
                                                                  • min stay varies
                                                                  • Nearest beach 15 mi
                                                                  • Swimming pool
                                                                  • Child Friendly

                                                                  Price per night from

                                                                  $178

                                                                  Price per night from

                                                                  $178

                                                                  Distance approx 19.18 km from Osprey

                                                                  (2) Excellent 

                                                                    28

                                                                    Paradise Cottage: Steps to the Gulf of Mexico beach and Sarasota Bay!

                                                                    Florida / Longboat Key

                                                                    Longboat Key house

                                                                    3 7 min stay varies

                                                                    • 3 bedrooms
                                                                    • sleeps 7
                                                                    • min stay varies
                                                                    • Nearest beach 0.25 mi
                                                                    • Child Friendly
                                                                    • Air conditioning

                                                                    Price per night from

                                                                    $229

                                                                    Price per night from

                                                                    $229

                                                                    Distance approx 7.19 km from Osprey

                                                                      6

                                                                      Cozy Condo in Downtown Venice

                                                                      Southwest Gulf Coast / Venice

                                                                      Venice apartment

                                                                      1 2 28 nights min

                                                                      • 1 bedroom
                                                                      • sleeps 2
                                                                      • 28 nights min
                                                                      • Nearest beach 0.08 mi
                                                                      • Swimming pool
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $46

                                                                      Price per night from

                                                                      $46

                                                                      Distance approx 5.27 km from Osprey Show on Map

                                                                        24

                                                                        Completely Remodeled Gulf Side Condo - Literally everything is new

                                                                        Florida / Siesta Key

                                                                        Siesta Key condo

                                                                        2 2 14 nights min

                                                                        • 2 bedrooms
                                                                        • sleeps 2
                                                                        • 14 nights min
                                                                        • Nearest beach 0.5 mi
                                                                        • Swimming pool
                                                                        • Child Friendly

                                                                        Price per night from

                                                                        $218

                                                                        Responds fast!
                                                                        avg. 2 hours 24 minutes

                                                                        Price per night from

                                                                        $218

                                                                        Distance approx 6.74 km from Osprey

                                                                          24

                                                                          NEW! Siesta Key Cottage - 4 Blocks to Main St!

                                                                          Florida / Siesta Key

                                                                          Siesta Key cottage

                                                                          2 3 30 nights min

                                                                          • 2 bedrooms
                                                                          • sleeps 3
                                                                          • 30 nights min
                                                                          • Child Friendly
                                                                          • Air conditioning
                                                                          • Pet Friendly

                                                                          Price per night from

                                                                          $63

                                                                          Responds fast!
                                                                          avg. 10 minutes

                                                                          Price per night from

                                                                          $63

                                                                          Distance approx 2.44 km from Osprey Show on Map

                                                                            24

                                                                            Monthly Rental, 2 bed, 2 bath, Ocean view.

                                                                            Southwest Gulf Coast / Sarasota

                                                                            Sarasota condo

                                                                            2 6 30 nights min

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

                                                                            Price per night from

                                                                            $115

                                                                            Price per night from

                                                                            $115

                                                                            Distance approx 17.43 km from Osprey

                                                                            (22) Very Good 

                                                                              15

                                                                              Gulf Coast Condo Minutes from Golf and Beaches

                                                                              Southwest Gulf Coast / Bradenton

                                                                              Bradenton condo

                                                                              2 6 6 nights min

                                                                              • 2 bedrooms
                                                                              • sleeps 6
                                                                              • 6 nights min
                                                                              • Nearest beach 8 mi
                                                                              • Swimming pool
                                                                              • Child Friendly

                                                                              Price per night from

                                                                              $144

                                                                              Price per night from

                                                                              $144