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385 Houses

    19

    Mile Zero Studio

    Florida Keys / Stock Island

    Stock Island studio

    Studio 2 min stay varies

    • Studio
    • sleeps 2
    • min stay varies
    • Child Friendly
    • Air conditioning
    • Pet Friendly

    Price per night from

    $43

    Price per night from

    $43

      24

      Southard Square Hideaway

      Florida Keys / Stock Island

      Stock Island condo

      1 4 min stay varies

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

      Price per night from

      $90

      Price per night from

      $90

        23

        William's Loft

        Florida Keys / Stock Island

        Stock Island cottage

        2 3 min stay varies

        • 2 bedrooms
        • sleeps 3
        • min stay varies
        • Swimming pool
        • Child Friendly
        • Pet Friendly

        Price per night from

        $83

        Price per night from

        $83

          23

          The Gallery

          Florida Keys / Stock Island

          Stock Island townhouse

          2 4 min stay varies

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

          Price per night from

          $73

          Price per night from

          $73

            29

            4BR Bahama Gardens Near Beach: Heated Pool, Spa, Lush Garden & Bikes!

            Florida Keys / Stock Island

            Stock Island house

            4 8 min stay varies

            • 4 bedrooms
            • sleeps 8
            • min stay varies
            • Swimming pool
            • Ask about children
            • Air conditioning

            Price per night from

            $715

            Price per night from

            $715

              27

              Lighthouse Villa

              Florida Keys / Stock Island

              Stock Island house

              3 8 min stay varies

              • 3 bedrooms
              • sleeps 8
              • min stay varies
              • Swimming pool
              • Child Friendly
              • Air conditioning

              Price per night from

              $193

              Price per night from

              $193

                12

                Mile Zero House

                Florida Keys / Stock Island

                Stock Island house

                2 4 min stay varies

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

                Price per night from

                $67

                Price per night from

                $67

                  22

                  Conch Republic Retreat

                  Florida Keys / Stock Island

                  Stock Island cottage

                  2 4 min stay varies

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

                  Price per night from

                  $107

                  Price per night from

                  $107

                    16

                    Boat House

                    Florida Keys / Stock Island

                    Stock Island house

                    1 2 min stay varies

                    • 1 bedroom
                    • sleeps 2
                    • min stay varies
                    • Swimming pool
                    • Child Friendly
                    • Air conditioning

                    Price per night from

                    $93

                    Price per night from

                    $93

                      23

                      70 foot Half million dollar yacht key west

                      Florida Keys / Stock Island

                      Stock Island boathouse

                      4 7 3 nights min

                      • 4 bedrooms
                      • sleeps 7
                      • 3 nights min
                      • Nearest beach 3 mi
                      • Swimming pool
                      • Child Friendly

                      Price per night from

                      $344

                      Price per night from

                      $344

                        24

                        Conch Corner

                        Florida Keys / Stock Island

                        Stock Island house

                        3 6 min stay varies

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

                        Price per night from

                        $117

                        Price per night from

                        $117

                          24

                          Shrimp Party

                          Florida Keys / Stock Island

                          Stock Island townhouse

                          2 4 min stay varies

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

                          Price per night from

                          $100

                          Price per night from

                          $100

                            24

                            Rosalie's House

                            Florida Keys / Stock Island

                            Stock Island house

                            3 8 min stay varies

                            • 3 bedrooms
                            • sleeps 8
                            • min stay varies
                            • Swimming pool
                            • Child Friendly
                            • Pet Friendly

                            Price per night from

                            $167

                            Price per night from

                            $167

                            (1) Excellent 

                              24

                              Poolside Paradise

                              Florida Keys / Stock Island

                              Stock Island house

                              2 4 min stay varies

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

                              Price per night from

                              $100

                              Price per night from

                              $100

                                28

                                Coral Palm

                                Florida Keys / Stock Island

                                Stock Island townhouse

                                3 8 min stay varies

                                • 3 bedrooms
                                • sleeps 8
                                • min stay varies
                                • Swimming pool
                                • Child Friendly
                                • Air conditioning

                                Price per night from

                                $215

                                Price per night from

                                $215

                                  21

                                  Key West Sanctuary

                                  Florida Keys / Stock Island

                                  Stock Island townhouse

                                  3 6 30 nights min

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

                                  Price per night from

                                  $107

                                  Price per night from

                                  $107

                                    15

                                    The small house

                                    Florida Keys / Stock Island

                                    Stock Island house

                                    2 4 min stay varies

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

                                    Price per night from

                                    $133

                                    Price per night from

                                    $133

                                      15

                                      Treetop Paradise

                                      Florida Keys / Stock Island

                                      Stock Island house

                                      2 6 min stay varies

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

                                      Price per night from

                                      $100

                                      Price per night from

                                      $100

                                        21

                                        Mermaid's Dream

                                        Florida Keys / Stock Island

                                        Stock Island condo

                                        2 4 30 nights min

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

                                        Price per night from

                                        $100

                                        Price per night from

                                        $100

                                          30

                                          Florida Keys / Stock Island

                                          Stock Island condo

                                          2 6 30 nights min

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

                                          Price per night from

                                          $134

                                          Price per night from

                                          $134

                                            6

                                            POND COTTAGE AT THE CLUB

                                            Florida Keys / Stock Island

                                            Stock Island townhouse

                                            2 4 30 nights min

                                            • 2 bedrooms
                                            • sleeps 4
                                            • 30 nights min
                                            • Child Friendly
                                            • Pet Friendly

                                            Price per night from

                                            $134

                                            Price per night from

                                            $134

                                              15

                                              LAST MINUTE OFFER! 44' Sailing Yacht & Other Boats

                                              Florida Keys / Stock Island

                                              Stock Island yacht

                                              4 10 2 nights min

                                              • 4 bedrooms
                                              • sleeps 10
                                              • 2 nights min
                                              • Nearest beach 2 mi
                                              • Child Friendly
                                              • Pet Friendly

                                              Price per night from

                                              $344

                                              Responds fast!
                                              avg. 1 hour 48 minutes

                                              Price per night from

                                              $344

                                                16

                                                SPECIAL OFFER! Like New! Sailing Yacht

                                                Florida Keys / Stock Island

                                                Stock Island yacht

                                                3 8 2 nights min

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

                                                Price per night from

                                                $344

                                                Responds fast!
                                                avg. 1 hour 48 minutes

                                                Price per night from

                                                $344

                                                Great rentals within 20 miles that match your search

                                                Distance approx 2.53 km from Stock Island Show on Map

                                                  13

                                                  Private and Immaculate 2 Bedroom Home with Private Fenced Yard

                                                  Florida Keys / Key West

                                                  Key West house

                                                  2 4 28 nights min

                                                  • 2 bedrooms
                                                  • sleeps 4
                                                  • 28 nights min
                                                  • Nearest beach 2 mi
                                                  • Child Friendly
                                                  • Air conditioning

                                                  Price per night from

                                                  $138

                                                  Price per night from

                                                  $138

                                                  Distance approx 16.46 km from Stock Island

                                                  (15) Very Good 

                                                    28

                                                    Family Retreat ocean front home with private pool

                                                    Florida Keys / Cudjoe Key

                                                    Cudjoe Key house

                                                    6 18 7 nights min

                                                    • 6 bedrooms
                                                    • sleeps 18
                                                    • 7 nights min
                                                    • Beach / lakeside relaxation
                                                    • Nearest beach 13 mi
                                                    • Swimming pool

                                                    Price per night from

                                                    $571

                                                    Price per night from

                                                    $571

                                                    Distance approx 4.08 km from Stock Island Show on Map

                                                      19

                                                      A Touch Of Havana In Key West

                                                      Florida Keys / Key West

                                                      Key West condo

                                                      2 4 7 nights min

                                                      • 2 bedrooms
                                                      • sleeps 4
                                                      • 7 nights min
                                                      • Nearest beach 0.5 mi
                                                      • Swimming pool
                                                      • Child Friendly

                                                      Price per night from

                                                      $352

                                                      Responds fast!
                                                      avg. 3 hours 31 minutes

                                                      Price per night from

                                                      $352

                                                      Distance approx 3.94 km from Stock Island Show on Map

                                                      (8) Very Good 

                                                        36

                                                        Villa Deja vu Key West ~ Weekly Rental

                                                        Florida Keys / Key West

                                                        Key West house

                                                        4 10 min stay varies

                                                        • 4 bedrooms
                                                        • sleeps 10
                                                        • min stay varies
                                                        • Swimming pool
                                                        • Ask about children
                                                        • Air conditioning
                                                        “Great stay over the 4th of July” The Villa Deja Vu was the perfect place for our group of 10. We were on vacation in Key West for a 30th birthday celebration and had a great experience. The house was wonderful, more than we could have imagined. The pi
                                                        …see more

                                                        Price per night from

                                                        $875

                                                        Price per night from

                                                        $875

                                                        Distance approx 16.42 km from Stock Island

                                                        (10) Excellent 

                                                          26

                                                          Tropical Paradise Oceanfront Home with Pool

                                                          Florida Keys / Cudjoe Key

                                                          Cudjoe Key house

                                                          2 6 7 nights min

                                                          • 2 bedrooms
                                                          • sleeps 6
                                                          • 7 nights min
                                                          • Beach / lakeside relaxation
                                                          • Nearest beach 13 mi
                                                          • Swimming pool
                                                          “The Perfect Little Get away” We (my husband and I and our 1 year-old) stayed at the Tropical Paradise Home for a week with another couple; and it was the perfect amount of space to enjoy each other's company but still have our own private areas. The
                                                          …see more

                                                          Price per night from

                                                          $400

                                                          Price per night from

                                                          $400

                                                          Distance approx 19.46 km from Stock Island

                                                            19

                                                            Gone Fishing

                                                            Lower Keys / Summerland Key

                                                            Summerland Key house

                                                            3 6 28 nights min

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

                                                            Price per night from

                                                            $211

                                                            Price per night from

                                                            $211

                                                            Distance approx 3.75 km from Stock Island Show on Map

                                                            (8) Very Good 

                                                              30

                                                              Classic Key West Estate ~ Weekly Rental

                                                              Florida Keys / Key West

                                                              Key West house

                                                              7 14 min stay varies

                                                              • 7 bedrooms
                                                              • sleeps 14
                                                              • min stay varies
                                                              • Swimming pool
                                                              • Ask about children
                                                              • Air conditioning

                                                              Price per night from

                                                              $1,500

                                                              Price per night from

                                                              $1,500

                                                              Distance approx 4.21 km from Stock Island Show on Map

                                                                13

                                                                One-bedroom suite in the heart of Old Key West

                                                                Florida Keys / Key West

                                                                Key West condo

                                                                1 4 3 nights min

                                                                • 1 bedroom
                                                                • sleeps 4
                                                                • 3 nights min
                                                                • Swimming pool
                                                                • Child Friendly
                                                                • Air conditioning

                                                                Price per night from

                                                                $218

                                                                Responds fast!
                                                                avg. 1 hour 39 minutes

                                                                Price per night from

                                                                $218

                                                                Distance approx 3.93 km from Stock Island Show on Map

                                                                  34

                                                                  House, 2 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 6)

                                                                  Florida Keys / Key West

                                                                  Key West house

                                                                  2 6 min stay varies

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

                                                                  Price per night from

                                                                  $716

                                                                  Price per night from

                                                                  $716

                                                                  Distance approx 3.91 km from Stock Island Show on Map

                                                                  (7) Average 

                                                                    22

                                                                    Key West Spa Villa ~ Weekly Rental

                                                                    Florida Keys / Key West

                                                                    Key West house

                                                                    4 10 min stay varies

                                                                    • 4 bedrooms
                                                                    • sleeps 10
                                                                    • min stay varies
                                                                    • Swimming pool
                                                                    • Ask about children
                                                                    • Air conditioning

                                                                    Price per night from

                                                                    $875

                                                                    Price per night from

                                                                    $875

                                                                    Distance approx 19.38 km from Stock Island

                                                                      12

                                                                      Blue Lagoon

                                                                      Lower Keys / Summerland Key

                                                                      Summerland Key house

                                                                      3 6 30 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 6
                                                                      • 30 nights min
                                                                      • Ask about children
                                                                      • Air conditioning
                                                                      • Pet Friendly

                                                                      Price per night from

                                                                      $200

                                                                      Price per night from

                                                                      $200

                                                                      Distance approx 17.87 km from Stock Island

                                                                        17

                                                                        Paradise Palms

                                                                        Lower Keys / Summerland Key

                                                                        Summerland Key house

                                                                        3 6 30 nights min

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

                                                                        Price per night from

                                                                        $134

                                                                        Price per night from

                                                                        $134

                                                                        Distance approx 12.89 km from Stock Island

                                                                          8

                                                                          Key's only real beach home.Gated, private, dock,pool

                                                                          Florida Keys / Key West

                                                                          Key West house

                                                                          3 6 7 nights min

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

                                                                          Price per night from

                                                                          $536

                                                                          Price per night from

                                                                          $536

                                                                          Distance approx 12.74 km from Stock Island

                                                                            26

                                                                            Private beach estate,gated,dock,and pool.

                                                                            Florida Keys / Key West

                                                                            Key West house

                                                                            5 10 28 nights min

                                                                            • 5 bedrooms
                                                                            • sleeps 10
                                                                            • 28 nights min
                                                                            • Nearest beach 0 mi
                                                                            • Swimming pool
                                                                            • Child Friendly

                                                                            Price per night from

                                                                            $743

                                                                            Price per night from

                                                                            $743

                                                                            Distance approx 4.01 km from Stock Island Show on Map

                                                                            (20) Excellent 

                                                                              22

                                                                              Harbor Walk Hideaways

                                                                              Florida Keys / Key West

                                                                              Key West b and b

                                                                              4 8 min stay varies

                                                                              • 4 bedrooms
                                                                              • sleeps 8
                                                                              • min stay varies
                                                                              • Beach / lakeside relaxation
                                                                              • Nearest beach 0.2 mi
                                                                              • Swimming pool
                                                                              “Location, Location, Location” We were a group of 8 and rented the entire compound! The place was in an amazing location that was easily accessible to everything. We had everything we needed onsite and if we had any questions, Phyllis was always just
                                                                              …see more

                                                                              Price per night from

                                                                              $900

                                                                              Price per night from

                                                                              $900