Summerland Key Rentals

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149 Houses

(1) Excellent 

    20

    Paradise n Summerland Key Cove

    Lower Keys / Summerland Key

    Summerland Key house

    3 10 30 nights min

    • 3 bedrooms
    • sleeps 10
    • 30 nights min
    • Beach / lakeside relaxation
    • Swimming pool
    • Child Friendly

    Price per night from

    $205

    Price per night from

    $205

    (1) Excellent 

      25

      Blue weekly vacation rental, great view. Heated private Pool.

      Lower Keys / Summerland Key

      Summerland Key house

      4 8 7 nights min

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

      Price per night from

      $393

      Price per night from

      $393

        0

        Spacious, canal front villa w/ private pool and hot tub - 3 dogs are welcome!

        Lower Keys / Summerland Key

        Summerland Key house

        3 6 28 nights min

        • 3 bedrooms
        • sleeps 6
        • 28 nights min
        • Swimming pool
        • Child Friendly
        • Car not necessary

        Price per night from

        $206

        Responds fast!
        avg. 1 hour 51 minutes

        Price per night from

        $206

          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

          $210

          Price per night from

          $210

            18

            Big Torch Retreat

            Lower Keys / Summerland Key

            Summerland Key house

            3 6 30 nights min

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

            Price per night from

            $100

            Price per night from

            $100

              17

              Another Day In Paradise

              Lower Keys / Summerland Key

              Summerland Key house

              3 8 28 nights min

              • 3 bedrooms
              • sleeps 8
              • 28 nights min
              • Child Friendly

              Price per night from

              $268

              Price per night from

              $268

                24

                Villa Cayo

                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

                $267

                Price per night from

                $267

                  18

                  Cruikshank

                  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

                  $168

                  Price per night from

                  $168

                    12

                    Caribbean House

                    Lower Keys / Summerland Key

                    Summerland Key house

                    2 4 30 nights min

                    • 2 bedrooms
                    • sleeps 4
                    • 30 nights min
                    • Ask about children
                    • Air conditioning
                    • Ask about pets

                    Price per night from

                    $87

                    Price per night from

                    $87

                      27

                      Key West--20 min, Stunning Views, Private, Ocean Access, Spacious, Resort-like

                      Lower Keys / Summerland Key

                      Summerland Key house

                      5 10 30 nights min

                      • 5 bedrooms
                      • sleeps 10
                      • 30 nights min
                      • Beach / lakeside relaxation
                      • Child Friendly
                      • Air conditioning

                      Price per night from

                      $764

                      Price per night from

                      $764

                        13

                        Family Friendly House In Paradise

                        Lower Keys / Summerland Key

                        Summerland Key house

                        5 8 30 nights min

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

                        Price per night from

                        $287

                        Price per night from

                        $287

                          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

                          (1) Excellent 

                            51

                            Oceanfront House

                            Lower Keys / Summerland Key

                            Summerland Key house

                            3 8 30 nights min

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

                            Price per night from

                            $421

                            Responds fast!
                            avg. 3 hours 34 minutes

                            Price per night from

                            $421

                              13

                              Gulf Shores

                              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

                              $107

                              Price per night from

                              $107

                                21

                                Salty Retreat

                                Lower Keys / Summerland Key

                                Summerland Key house

                                3 8 28 nights min

                                • 3 bedrooms
                                • sleeps 8
                                • 28 nights min
                                • Child Friendly

                                Price per night from

                                $447

                                Price per night from

                                $447

                                  13

                                  Casa Turquesa

                                  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

                                  $217

                                  Price per night from

                                  $217

                                  (1) Very Good 

                                    14

                                    Direct Atlantic Ocean front private boat ramp dock

                                    Lower Keys / Summerland Key

                                    Summerland Key house

                                    2 6 30 nights min

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

                                    Price per night from

                                    $161

                                    Price per night from

                                    $161

                                      14

                                      Cove Isles

                                      Lower Keys / Summerland Key

                                      Summerland Key house

                                      2 4 30 nights min

                                      • 2 bedrooms
                                      • sleeps 4
                                      • 30 nights min
                                      • Ask about children
                                      • Air conditioning
                                      • Ask about pets

                                      Price per night from

                                      $120

                                      Price per night from

                                      $120

                                        22

                                        Caribbean Dream

                                        Lower Keys / Summerland Key

                                        Summerland Key house

                                        4 8 30 nights min

                                        • 4 bedrooms
                                        • sleeps 8
                                        • 30 nights min
                                        • Ask about children
                                        • Air conditioning
                                        • Ask about pets

                                        Price per night from

                                        $200

                                        Price per night from

                                        $200

                                          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

                                          $152

                                          Price per night from

                                          $152

                                          Great rentals within 20 miles that match your search

                                          Distance approx 2.23 km from Summerland Key Show on Map

                                            19

                                            Bahia Azul

                                            Florida Keys / Ramrod Key

                                            Ramrod Key house

                                            4 8 30 nights min

                                            • 4 bedrooms
                                            • sleeps 8
                                            • 30 nights min
                                            • Ask about children
                                            • Air conditioning
                                            • Ask about pets

                                            Price per night from

                                            $229

                                            Price per night from

                                            $229

                                            Distance approx 3.67 km from Summerland Key Show on Map

                                              17

                                              Buccaneer Boathouse

                                              Lower Keys / Little Torch Key

                                              Little Torch Key house

                                              2 6 30 nights min

                                              • 2 bedrooms
                                              • sleeps 6
                                              • 30 nights min
                                              • Child Friendly

                                              Price per night from

                                              $113

                                              Price per night from

                                              $113

                                              Distance approx 2.38 km from Summerland Key Show on Map

                                                14

                                                Cudjoe Cottage

                                                Florida Keys / Cudjoe Key

                                                Cudjoe Key house

                                                2 4 30 nights min

                                                • 2 bedrooms
                                                • sleeps 4
                                                • 30 nights min
                                                • Ask about children
                                                • Air conditioning
                                                • Ask about pets

                                                Price per night from

                                                $113

                                                Price per night from

                                                $113

                                                Distance approx 6.35 km from Summerland Key Show on Map

                                                  16

                                                  Island Time 2 (half of duplex)

                                                  Florida Keys / Big Pine Key

                                                  Big Pine 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

                                                  $100

                                                  Price per night from

                                                  $100

                                                  Distance approx 2.45 km from Summerland Key Show on Map

                                                    19

                                                    Atlantic Breeze

                                                    Florida Keys / Cudjoe Key

                                                    Cudjoe 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

                                                    $133

                                                    Price per night from

                                                    $133

                                                    Distance approx 6.49 km from Summerland Key

                                                    (1)  

                                                      16

                                                      Our Island Thing

                                                      Florida Keys / Big Pine Key

                                                      Big Pine Key house

                                                      4 8 30 nights min

                                                      • 4 bedrooms
                                                      • sleeps 8
                                                      • 30 nights min
                                                      • Ask about children
                                                      • Air conditioning
                                                      • Ask about pets

                                                      Price per night from

                                                      $200

                                                      Price per night from

                                                      $200

                                                      Distance approx 18.96 km from Summerland Key

                                                        14

                                                        Catchin' Moments Charters

                                                        Florida Keys / Key West

                                                        Key West yacht

                                                        4 8 3 nights min

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

                                                        Price per night from

                                                        $1,085

                                                        Price per night from

                                                        $1,085

                                                        Distance approx 3.62 km from Summerland Key Show on Map

                                                          16

                                                          Charming Elevated Waterfront Home

                                                          Florida Keys / Big Pine Key

                                                          Big Pine Key house

                                                          1 4 30 nights min

                                                          • 1 bedroom
                                                          • sleeps 4
                                                          • 30 nights min
                                                          • Child Friendly
                                                          • Air conditioning
                                                          • Ask about pets

                                                          Price per night from

                                                          $163

                                                          Responds fast!
                                                          avg. 3 hours 2 minutes

                                                          Price per night from

                                                          $163

                                                          Distance approx 2.05 km from Summerland Key Show on Map

                                                            62

                                                            Home with Open Ocean & spectacular Sunset views and Private Launch.

                                                            Florida Keys / Cudjoe Key

                                                            Cudjoe Key house

                                                            2 6 28 nights min

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

                                                            Price per night from

                                                            $143

                                                            Responds fast!
                                                            avg. 2 hours 42 minutes

                                                            Price per night from

                                                            $143

                                                            Distance approx 6.98 km from Summerland Key

                                                              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

                                                              $742

                                                              Price per night from

                                                              $742

                                                              Distance approx 1.91 km from Summerland Key Show on Map

                                                                14

                                                                Catch of the Day!

                                                                Florida Keys / Cudjoe Key

                                                                Cudjoe Key house

                                                                2 6 30 nights min

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

                                                                Price per night from

                                                                $110

                                                                Price per night from

                                                                $110

                                                                Distance approx 2.49 km from Summerland Key Show on Map

                                                                (1)  

                                                                  10

                                                                  Ramrod Retreat

                                                                  Florida Keys / Ramrod Key

                                                                  Ramrod 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

                                                                  $97

                                                                  Price per night from

                                                                  $97

                                                                  Distance approx 3.59 km from Summerland Key Show on Map

                                                                  (1) Excellent 

                                                                    18

                                                                    Pirates Pointe

                                                                    Lower Keys / Little Torch Key

                                                                    Little Torch Key house

                                                                    3 6 30 nights min

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

                                                                    Price per night from

                                                                    $130

                                                                    Price per night from

                                                                    $130

                                                                    Distance approx 2.15 km from Summerland Key Show on Map

                                                                      15

                                                                      Owl's Nest

                                                                      Florida Keys / Ramrod Key

                                                                      Ramrod 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

                                                                      $120

                                                                      Price per night from

                                                                      $120

                                                                      Distance approx 9.55 km from Summerland Key

                                                                        8

                                                                        Bay Pointe

                                                                        Florida Keys / Sugarloaf

                                                                        Sugarloaf house

                                                                        3 6 30 nights min

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

                                                                        Price per night from

                                                                        $143

                                                                        Price per night from

                                                                        $143

                                                                        Distance approx 7.55 km from Summerland Key

                                                                          9

                                                                          Key's only real beach home. Dock and pool.

                                                                          Florida Keys / Key West

                                                                          Key West house

                                                                          2 4 min stay varies

                                                                          • 2 bedrooms
                                                                          • sleeps 4
                                                                          • min stay varies
                                                                          • Nearest beach 0 mi
                                                                          • Swimming pool
                                                                          • Child Friendly

                                                                          Price per night from

                                                                          $343

                                                                          Price per night from

                                                                          $343

                                                                          Distance approx 2.49 km from Summerland Key Show on Map

                                                                            11

                                                                            St. Croix

                                                                            Florida Keys / Ramrod Key

                                                                            Ramrod Key house

                                                                            2 4 30 nights min

                                                                            • 2 bedrooms
                                                                            • sleeps 4
                                                                            • 30 nights min
                                                                            • Ask about children
                                                                            • Air conditioning
                                                                            • Pet Friendly

                                                                            Price per night from

                                                                            $89

                                                                            Price per night from

                                                                            $89

                                                                            Distance approx 2.15 km from Summerland Key Show on Map

                                                                              16

                                                                              5 O'Clock Somewhere

                                                                              Florida Keys / Cudjoe Key

                                                                              Cudjoe Key house

                                                                              2 4 30 nights min

                                                                              • 2 bedrooms
                                                                              • sleeps 4
                                                                              • 30 nights min
                                                                              • Ask about children
                                                                              • Air conditioning
                                                                              • Ask about pets

                                                                              Price per night from

                                                                              $92

                                                                              Price per night from

                                                                              $92