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124 Houses

    24

    NEW! Updated Osteen Home w/Dock on St. Johns River

    Florida / Osteen

    Osteen house

    4 8 3 nights min

    • 4 bedrooms
    • sleeps 8
    • 3 nights min
    • Child Friendly
    • Air conditioning

    Price per night from

    $200

    Responds fast!
    avg. 38 minutes

    Price per night from

    $200

    Great rentals within 20 miles that match your search

    Distance approx 17.24 km from Osteen

      15

      Golf Course Condo Only 10 minutes From The Beach!

      Florida / New Smyrna Beach

      New Smyrna Beach house

      2 4 30 nights min

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

      Price per night from

      $95

      Price per night from

      $95

      Distance approx 16.97 km from Osteen

        24

        5 Bedroom 4 Full Bath Executive Pool Home

        Florida / Port Orange

        Port Orange house

        5 12 7 nights min

        • 5 bedrooms
        • sleeps 12
        • 7 nights min
        • Swimming pool
        • Child Friendly
        • Air conditioning

        Price per night from

        $451

        Price per night from

        $451

        Distance approx 4.43 km from Osteen Show on Map

        (2) Excellent 

          27

          Ninovan on the Shore, A river retreat with history

          Central Florida / Sanford

          Sanford house

          4 13 3 nights min

          • 4 bedrooms
          • sleeps 13
          • 3 nights min
          • Beach / lakeside relaxation
          • Child Friendly
          • Air conditioning

          Price per night from

          $325

          Responds fast!
          avg. 1 hour 39 minutes

          Price per night from

          $325

          Distance approx 18.85 km from Osteen

            20

            UCF - European Art Gallery

            Florida / Alafaya

            Alafaya house

            2 4 1 night min

            • 2 bedrooms
            • sleeps 4
            • 1 night min
            • Nearest beach 60 mi
            • Child Friendly
            • Air conditioning

            Price per night from

            $143

            Price per night from

            $143

            Distance approx 16.62 km from Osteen

            (2) Excellent 

              24

              Splendid Port Orange House w/ Private Pool!

              Florida / Port Orange

              Port Orange house

              4 6 3 nights min

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

              Price per night from

              $280

              Responds fast!
              avg. 20 minutes

              Price per night from

              $280

              Distance approx 19 km from Osteen

              (11) Very Good 

                8

                Mandy's Waterfront Oak Hill Paradise

                Florida / New Smyrna Beach

                New Smyrna Beach house

                2 6 min stay varies

                • 2 bedrooms
                • sleeps 6
                • min stay varies
                • Beach / lakeside relaxation
                • Child Friendly
                • Air conditioning

                Price per night from

                $57

                Responds fast!
                avg. 3 hours 2 minutes

                Price per night from

                $57

                Distance approx 17.9 km from Osteen

                  28

                  DeLand Florida Vacation Rental

                  Florida / DeLand

                  DeLand house

                  2 7 5 nights min

                  • 2 bedrooms
                  • sleeps 7
                  • 5 nights min
                  • Child Friendly
                  • Air conditioning
                  • Pet Friendly

                  Price per night from

                  $166

                  Price per night from

                  $166

                  Distance approx 17.75 km from Osteen

                    27

                    Cozy Longwood Home w/Screened-In Porch & Gas Grill

                    Florida / Longwood

                    Longwood house

                    4 9 min stay varies

                    • 4 bedrooms
                    • sleeps 9
                    • min stay varies
                    • Child Friendly
                    • Air conditioning

                    Price per night from

                    $160

                    Responds fast!
                    avg. 19 minutes

                    Price per night from

                    $160

                    Distance approx 7.19 km from Osteen Show on Map

                      27

                      NEW! Lavish Sanford Apt. w/Gourmet Kitchen & Patio

                      Central Florida / Sanford

                      Sanford apartment

                      1 2 3 nights min

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

                      Price per night from

                      $137

                      Responds fast!
                      avg. 19 minutes

                      Price per night from

                      $137

                      Distance approx 4.05 km from Osteen Show on Map

                      (8) Very Good 

                        5

                        Pleasant Point River Retreat

                        Florida / Geneva

                        Geneva log cabin

                        1 3 2 nights min

                        • 1 bedroom
                        • sleeps 3
                        • 2 nights min
                        • Beach / lakeside relaxation
                        • Nearest beach 40 mi
                        • Air conditioning

                        Price per night from

                        $204

                        Responds fast!
                        avg. 1 hour 17 minutes

                        Price per night from

                        $204

                        Distance approx 7.13 km from Osteen Show on Map

                        (1) Excellent 

                          16

                          2BR BUNGALOW IN SANFORD HISTORIC DISTRICT

                          Central Florida / Sanford

                          Sanford bungalow

                          2 4 3 nights min

                          • 2 bedrooms
                          • sleeps 4
                          • 3 nights min
                          • Nearest beach 35 mi
                          • Air conditioning
                          • Private garden

                          Price per night from

                          $149

                          Price per night from

                          $149

                          Distance approx 17.92 km from Osteen

                            13

                            Home, Sweet Home Orlando

                            Florida / Aloma

                            Aloma house

                            4 8 4 nights min

                            • 4 bedrooms
                            • sleeps 8
                            • 4 nights min
                            • Swimming pool
                            • Child Friendly
                            • Air conditioning

                            Price per night from

                            $166

                            Price per night from

                            $166

                            Distance approx 6.83 km from Osteen Show on Map

                              16

                              Home Away From Home Private Pool Home

                              Florida / Deltona Pines

                              Deltona Pines house

                              3 8 1 night min

                              • 3 bedrooms
                              • sleeps 8
                              • 1 night min
                              • Swimming pool
                              • Child Friendly
                              • Air conditioning

                              Price per night from

                              $149

                              Price per night from

                              $149

                              Distance approx 17.12 km from Osteen

                                22

                                NEW! Artsy Longwood Condo near Cranes Roost Park!

                                Florida / Longwood

                                Longwood condo

                                2 4 min stay varies

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

                                Price per night from

                                $109

                                Responds fast!
                                avg. 38 minutes

                                Price per night from

                                $109

                                Distance approx 7.18 km from Osteen Show on Map

                                  24

                                  Gorgeous Sanford House w/ Yard - Walk to Downtown!

                                  Central Florida / Sanford

                                  Sanford apartment

                                  2 6 3 nights min

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

                                  Price per night from

                                  $171

                                  Responds fast!
                                  avg. 39 minutes

                                  Price per night from

                                  $171

                                  Distance approx 15.79 km from Osteen

                                    61

                                    Swiss- FL B&B, with breakfast, STUDIO has kitchen, near Universy/City (y)

                                    Florida / DeLand

                                    DeLand b and b

                                    1 1 1 night min

                                    • 1 bedroom
                                    • sleeps 1
                                    • 1 night min
                                    • Beach / lakeside relaxation
                                    • Nearest beach 20 mi
                                    • Air conditioning

                                    Price per night from

                                    $79

                                    Responds fast!
                                    avg. 1 hour 41 minutes

                                    Price per night from

                                    $79

                                    Distance approx 12.22 km from Osteen

                                      7

                                      Beautiful 3 Bedrom House In Orange City

                                      Florida / Orange City

                                      Orange City house

                                      3 8 7 nights min

                                      • 3 bedrooms
                                      • sleeps 8
                                      • 7 nights min
                                      • Child Friendly
                                      • Pet Friendly

                                      Price per night from

                                      $513

                                      Price per night from

                                      $513

                                      Distance approx 17.72 km from Osteen

                                        24

                                        Golf, Tennis, Beach, and Quiet Relaxation

                                        Florida / New Smyrna Beach

                                        New Smyrna Beach house

                                        3 8 30 nights min

                                        • 3 bedrooms
                                        • sleeps 8
                                        • 30 nights min
                                        • Child Friendly
                                        • Air conditioning

                                        Price per night from

                                        $106

                                        Price per night from

                                        $106

                                        Distance approx 16.61 km from Osteen

                                          19

                                          Gorgeous 2BR/2BA Rental - Close to Disney

                                          Florida / Longwood

                                          Longwood house

                                          2 5 2 nights min

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

                                          Price per night from

                                          $147

                                          Responds fast!
                                          avg. 1 hour 24 minutes

                                          Price per night from

                                          $147

                                          Distance approx 10.86 km from Osteen

                                            22

                                            3150ft2 - Room 4 Rent House Share golf course pool

                                            Central Florida / Orlando

                                            Orlando house

                                            3 6 5 nights min

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

                                            Price per night from

                                            $228

                                            Price per night from

                                            $228

                                            Distance approx 7.16 km from Osteen Show on Map

                                              5

                                              The Chef's Suite

                                              Central Florida / Sanford

                                              Sanford condo

                                              1 2 1 night min

                                              • 1 bedroom
                                              • sleeps 2
                                              • 1 night min
                                              • Child Friendly

                                              Price per night from

                                              $131

                                              Price per night from

                                              $131

                                              Distance approx 8.61 km from Osteen

                                                30

                                                Beautiful Country Home, Vacation Destination

                                                Florida / Lake Helen

                                                Lake Helen house

                                                3 8 1 night min

                                                • 3 bedrooms
                                                • sleeps 8
                                                • 1 night min
                                                • Child Friendly
                                                • Air conditioning
                                                • Private garden

                                                Price per night from

                                                $143

                                                Price per night from

                                                $143

                                                Distance approx 10.09 km from Osteen

                                                (4) Excellent 

                                                  30

                                                  Floating Cottage . . .afloat on the St. Johns River in Florida

                                                  Central Florida / Sanford

                                                  Sanford cottage

                                                  1 4 2 nights min

                                                  • 1 bedroom
                                                  • sleeps 4
                                                  • 2 nights min
                                                  • Nearest beach 24 mi
                                                  • Swimming pool
                                                  • Child Friendly

                                                  Price per night from

                                                  $159

                                                  Responds fast!
                                                  avg. 1 hour 6 minutes

                                                  Price per night from

                                                  $159

                                                  Distance approx 18.69 km from Osteen

                                                    26

                                                    Kate's Places / Ming - Golf & Lake Home near Beach

                                                    Florida / New Smyrna Beach

                                                    New Smyrna Beach townhouse

                                                    3 6 min stay varies

                                                    • 3 bedrooms
                                                    • sleeps 6
                                                    • min stay varies
                                                    • Beach / lakeside relaxation
                                                    • Swimming pool
                                                    • Child Friendly

                                                    Price per night from

                                                    $94

                                                    Price per night from

                                                    $94

                                                    Distance approx 15.79 km from Osteen

                                                    (1) Excellent 

                                                      60

                                                      Swiss-Floridian B&B, with breakfast, Master Suite, near University /City

                                                      Florida / DeLand

                                                      DeLand b and b

                                                      1 4 1 night min

                                                      • 1 bedroom
                                                      • sleeps 4
                                                      • 1 night min
                                                      • Beach / lakeside relaxation
                                                      • Nearest beach 20 mi
                                                      • Child Friendly

                                                      Price per night from

                                                      $96

                                                      Responds fast!
                                                      avg. 1 hour 41 minutes

                                                      Price per night from

                                                      $96

                                                      Distance approx 18.66 km from Osteen

                                                        26

                                                        Kate's Places/ Jasmine - Golfer's Dream Near Beach

                                                        Florida / New Smyrna Beach

                                                        New Smyrna Beach townhouse

                                                        3 7 60 nights min

                                                        • 3 bedrooms
                                                        • sleeps 7
                                                        • 60 nights min
                                                        • Beach / lakeside relaxation
                                                        • Swimming pool
                                                        • Child Friendly

                                                        Price per night from

                                                        $86

                                                        Price per night from

                                                        $86

                                                        Distance approx 15.79 km from Osteen

                                                        (1) Excellent 

                                                          60

                                                          Swiss-Floridian B&B,.with breakfast, has a kitchen, near University+City

                                                          Florida / DeLand

                                                          DeLand b and b

                                                          1 1 1 night min

                                                          • 1 bedroom
                                                          • sleeps 1
                                                          • 1 night min
                                                          • Beach / lakeside relaxation
                                                          • Nearest beach 20 mi
                                                          • Air conditioning

                                                          Price per night from

                                                          $79

                                                          Responds fast!
                                                          avg. 1 hour 41 minutes

                                                          Price per night from

                                                          $79

                                                          Distance approx 19.16 km from Osteen

                                                          (2) Excellent 

                                                            4

                                                            New Smyrna Beach Hideaway Villa

                                                            Florida / New Smyrna Beach

                                                            New Smyrna Beach townhouse

                                                            2 5 7 nights min

                                                            • 2 bedrooms
                                                            • sleeps 5
                                                            • 7 nights min
                                                            • Child Friendly
                                                            • Air conditioning
                                                            • Pet Friendly

                                                            Price per night from

                                                            $155

                                                            Price per night from

                                                            $155

                                                            Distance approx 2.25 km from Osteen Show on Map

                                                            (2) Excellent 

                                                              21

                                                              Luxury Florida Pool home 2 Bedroom 2 Bath

                                                              Florida / Deltona

                                                              Deltona house

                                                              2 6 1 night min

                                                              • 2 bedrooms
                                                              • sleeps 6
                                                              • 1 night min
                                                              • Beach / lakeside relaxation
                                                              • Nearest beach 22 mi
                                                              • Swimming pool

                                                              Price per night from

                                                              $120

                                                              Responds fast!
                                                              avg. 1 hour 20 minutes

                                                              Price per night from

                                                              $120

                                                              Distance approx 18.7 km from Osteen

                                                              (4) Excellent 

                                                                20

                                                                PRIVATE Waterfront Home * gorgeous POOL * 4 bedrooms * 3 1/2 baths* huge kitchen

                                                                Florida / New Smyrna Beach

                                                                New Smyrna Beach house

                                                                4 8 6 nights min

                                                                • 4 bedrooms
                                                                • sleeps 8
                                                                • 6 nights min
                                                                • Beach / lakeside relaxation
                                                                • Swimming pool
                                                                • Child Friendly
                                                                “We wish we could have stayed longer!” When you're ready to really relax, this home is the perfect place. Conveniently located near great amenities, yet secluded and quiet enough for recharging on your own. We stayed in this house with 4 other couples

                                                                Price per night from

                                                                $497

                                                                Price per night from

                                                                $497

                                                                Distance approx 18.28 km from Osteen

                                                                  19

                                                                  Ocean Front Boardwalk Property

                                                                  Florida / Wildwood

                                                                  Wildwood studio

                                                                  Studio 8 7 nights min

                                                                  • Studio
                                                                  • sleeps 8
                                                                  • 7 nights min
                                                                  • Child Friendly
                                                                  • Air conditioning

                                                                  Price per night from

                                                                  $457

                                                                  Price per night from

                                                                  $457

                                                                  Distance approx 19.36 km from Osteen

                                                                    39

                                                                    SPRING!! Kate's Places - LUXURY RIVERSIDE VILLA-BOAT DOCK 2b/2b NEW RENOVATION

                                                                    Florida / New Smyrna Beach

                                                                    New Smyrna Beach villa

                                                                    2 4 min stay varies

                                                                    • 2 bedrooms
                                                                    • sleeps 4
                                                                    • min stay varies
                                                                    • Beach / lakeside relaxation
                                                                    • Nearest beach 3 mi
                                                                    • Child Friendly

                                                                    Price per night from

                                                                    $86

                                                                    Price per night from

                                                                    $86

                                                                    Distance approx 11.91 km from Osteen

                                                                      24

                                                                      NEW! Sleek 4BR Lake Mary House w/Private Backyard

                                                                      Florida / Lake Mary

                                                                      Lake Mary house

                                                                      4 8 2 nights min

                                                                      • 4 bedrooms
                                                                      • sleeps 8
                                                                      • 2 nights min
                                                                      • Child Friendly
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $228

                                                                      Responds fast!
                                                                      avg. 41 minutes

                                                                      Price per night from

                                                                      $228

                                                                      Distance approx 16.72 km from Osteen

                                                                        24

                                                                        Spacious 3BR Orlando House w/Wifi, Private Screened Porch & Lush Landscaping - Just 30 Minutes from Disney/Universal Studios! Close to Lakes, Shopping, Beaches & More!

                                                                        Florida / Chuluota

                                                                        Chuluota house

                                                                        3 8 min stay varies

                                                                        • 3 bedrooms
                                                                        • sleeps 8
                                                                        • min stay varies
                                                                        • Child Friendly
                                                                        • Air conditioning
                                                                        Inquire for Rates

                                                                        Responds fast!
                                                                        avg. 41 minutes

                                                                        Inquire for Rates

                                                                        Distance approx 19.39 km from Osteen

                                                                        (1) Excellent 

                                                                          41

                                                                          SPRING! Kate's Places - DIRECT RIVERFRONT PRIVATE BOAT DOCK LUXURY 2B/2B VILLA

                                                                          Florida / New Smyrna Beach

                                                                          New Smyrna Beach villa

                                                                          2 4 min stay varies

                                                                          • 2 bedrooms
                                                                          • sleeps 4
                                                                          • min stay varies
                                                                          • Nearest beach 3 mi
                                                                          • Child Friendly
                                                                          • Air conditioning

                                                                          Price per night from

                                                                          $124

                                                                          Price per night from

                                                                          $124

                                                                          Distance approx 18.21 km from Osteen

                                                                            11

                                                                            RV BOAT Parking 5 MINUTES DRIVE TO OCEAN

                                                                            Florida / New Smyrna Beach

                                                                            New Smyrna Beach bungalow

                                                                            1 4 7 nights min

                                                                            • 1 bedroom
                                                                            • sleeps 4
                                                                            • 7 nights min
                                                                            • Nearest beach 2 mi
                                                                            • Air conditioning
                                                                            • Pet Friendly

                                                                            Price per night from

                                                                            $86

                                                                            Responds fast!
                                                                            avg. 56 minutes

                                                                            Price per night from

                                                                            $86

                                                                            Distance approx 15.79 km from Osteen

                                                                            (3) Excellent 

                                                                              59

                                                                              Swiss-Floridian B&B, with breakfast, Apartment near University and Downtown

                                                                              Florida / DeLand

                                                                              DeLand apartment

                                                                              1 4 1 night min

                                                                              • 1 bedroom
                                                                              • sleeps 4
                                                                              • 1 night min
                                                                              • Beach / lakeside relaxation
                                                                              • Nearest beach 20 mi
                                                                              • Child Friendly
                                                                              “Home away from home!” We loved this little getaway and hated to leave! My mom,dad and my sister and I stayed in the garage apartment perfect for four! It was a beautiful setting and the apartment was spotless and adorable, just perfect for our stay.

                                                                              Price per night from

                                                                              $102

                                                                              Responds fast!
                                                                              avg. 1 hour 41 minutes

                                                                              Price per night from

                                                                              $102