Grassy Key Rentals

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384 Houses

(3) Very Good 

    45

    SPRING DEALS at Relax Away- SOMBRERO BEACH- NEW 4BDRM W/ 40FT DOCK & POOL

    Marathon / Grassy Key

    Grassy Key house

    4 10 min stay varies

    • 4 bedrooms
    • sleeps 10
    • min stay varies
    • Nearest beach 2 mi
    • Swimming pool
    • Child Friendly

    Price per night from

    $338

    Responds fast!
    avg. 2 hours 23 minutes

    Price per night from

    $338

    (4) Very Good 

      37

      Unit 10, Furnished Studio located 50 yards from ocean

      Marathon / Grassy Key

      Grassy Key apartment

      2 min stay varies

      • sleeps 2
      • min stay varies
      • Swimming pool
      • Air conditioning
      • Private garden

      Price per night from

      $172

      Responds fast!
      avg. 1 hour 52 minutes

      Price per night from

      $172

      (1) Excellent 

        27

        Beachfront Condo with Panoramic Ocean View! Paradise in the Florida Keys!

        Marathon / Grassy Key

        Grassy Key condo

        2 4 6 nights min

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

        Price per night from

        $258

        Responds fast!
        avg. 1 hour 10 minutes

        Price per night from

        $258

          33

          Sunset Catch- Gulf Front Home Incredible Views Pool Dock private and spacious

          Marathon / Grassy Key

          Grassy Key house

          3 8 7 nights min

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

          Price per night from

          $524

          Responds fast!
          avg. 1 hour 51 minutes

          Price per night from

          $524

          (2) Excellent 

            38

            Unit 9, Furnished Studio located 50 yards from ocean

            Marathon / Grassy Key

            Grassy Key apartment

            2 min stay varies

            • sleeps 2
            • min stay varies
            • Swimming pool
            • Air conditioning

            Price per night from

            $172

            Responds fast!
            avg. 1 hour 52 minutes

            Price per night from

            $172

              36

              Efficiency 8a, located 50 yards from Ocean

              Marathon / Grassy Key

              Grassy Key studio

              Studio 2 min stay varies

              • Studio
              • sleeps 2
              • min stay varies
              • Swimming pool
              • Air conditioning
              • Private garden

              Price per night from

              $161

              Responds fast!
              avg. 1 hour 52 minutes

              Price per night from

              $161

              (5) Excellent 

                17

                P58 Grassy Key Delight--- 4 Bedroom With Pool

                Marathon / Grassy Key

                Grassy Key house

                4 8 7 nights min

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

                Price per night from

                $428

                Price per night from

                $428

                Great rentals within 20 miles that match your search

                Distance approx 2.9 km from Grassy Key

                (1) Excellent 

                  27

                  WOW – waterfront, boat lift, private heated pool, walk to beach and shops!

                  Florida Keys / Marathon

                  Marathon house

                  2 6 7 nights min

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

                  Price per night from

                  $288

                  Price per night from

                  $288

                  Distance approx 0.1 km from Grassy Key

                  (5) Excellent 

                    23

                    Indigo Reef, 32' dock, Marathon FL

                    Florida Keys / Marathon

                    Marathon villa

                    3 6 7 nights min

                    • 3 bedrooms
                    • sleeps 6
                    • 7 nights min
                    • Beach / lakeside relaxation
                    • Swimming pool
                    • Child Friendly

                    Price per night from

                    $460

                    Price per night from

                    $460

                    Distance approx 0.1 km from Grassy Key

                      98

                      Jack's Flat

                      Florida Keys / Key Colony Beach

                      Key Colony Beach house

                      2 8 2 nights min

                      • 2 bedrooms
                      • sleeps 8
                      • 2 nights min
                      • Car not necessary

                      Price per night from

                      $433

                      Price per night from

                      $433

                      Distance approx 0.1 km from Grassy Key

                        8

                        Million $$ Pool Home

                        Florida Keys / Key Colony Beach

                        Key Colony Beach house

                        3 8 7 nights min

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

                        Price per night from

                        $409

                        Price per night from

                        $409

                        Distance approx 13.49 km from Grassy Key

                          11

                          Long Key, Fl Keys

                          Florida Keys / Long Key

                          Long Key apartment

                          2 6 30 nights min

                          • 2 bedrooms
                          • sleeps 6
                          • 30 nights min
                          • Beach / lakeside relaxation
                          • Swimming pool
                          • Child Friendly

                          Price per night from

                          $3,432

                          Price per night from

                          $3,432

                          Distance approx 1.27 km from Grassy Key

                            24

                            Key Colony Beach Home

                            Florida Keys / Key Colony Beach

                            Key Colony Beach house

                            2 6 7 nights min

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

                            Price per night from

                            $206

                            Price per night from

                            $206

                            Distance approx 2.28 km from Grassy Key

                            (6) Very Good 

                              32

                              Coco Plum Beach 2 BR/ BA Fantastic Condo

                              Florida Keys / Marathon

                              Marathon condo

                              2 6 6 nights min

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

                              Price per night from

                              $196

                              Price per night from

                              $196

                              Distance approx 3.34 km from Grassy Key

                              (2) Excellent 

                                17

                                East Sister Rock Island

                                Marathon / Marathon Shores

                                Marathon Shores house

                                3 8 7 nights min

                                • 3 bedrooms
                                • sleeps 8
                                • 7 nights min
                                • Beach / lakeside relaxation
                                • Swimming pool
                                • Child Friendly

                                Price per night from

                                $1,396

                                Price per night from

                                $1,396

                                Distance approx 0.1 km from Grassy Key

                                (4) Excellent 

                                  43

                                  ***NEW 3D Tour Indigo Reef Luxury Villa Exquisite "Latitude Adjustment"! #33

                                  Florida Keys / Marathon

                                  Marathon villa

                                  3 6 7 nights min

                                  • 3 bedrooms
                                  • sleeps 6
                                  • 7 nights min
                                  • Nearest beach 7 mi
                                  • Child Friendly

                                  Price per night from

                                  $340

                                  Responds fast!
                                  avg. 2 hours 36 minutes

                                  Price per night from

                                  $340

                                  Distance approx 1.64 km from Grassy Key

                                    16

                                    Key Colony Beach FL - Cay Condo

                                    Florida Keys / Key Colony Beach

                                    Key Colony Beach condo

                                    2 6 14 nights min

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

                                    Price per night from

                                    $230

                                    Price per night from

                                    $230

                                    Distance approx 1.09 km from Grassy Key

                                    (2) Excellent 

                                      25

                                      P27 Sunsplash Paradise - Pool home with private beach access!

                                      Florida Keys / Key Colony Beach

                                      Key Colony Beach house

                                      3 8 7 nights min

                                      • 3 bedrooms
                                      • sleeps 8
                                      • 7 nights min
                                      • Nearest beach 0.1 mi
                                      • Swimming pool
                                      • Child Friendly

                                      Price per night from

                                      $266

                                      Price per night from

                                      $266

                                      Distance approx 1.51 km from Grassy Key

                                      (1) Very Good 

                                        25

                                        House on 7th ST in KEY Colony Beach W/CABANA CLUB

                                        Florida Keys / Key Colony Beach

                                        Key Colony Beach house

                                        2 6 7 nights min

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

                                        Price per night from

                                        $214

                                        Responds fast!
                                        avg. 1 hour 19 minutes

                                        Price per night from

                                        $214

                                        Distance approx 3.01 km from Grassy Key

                                        (1) Excellent 

                                          29

                                          7 ROOM NEW VACATIONAL HOME

                                          Florida Keys / Marathon

                                          Marathon house

                                          7 14 7 nights min

                                          • 7 bedrooms
                                          • sleeps 14
                                          • 7 nights min
                                          • Swimming pool
                                          • Child Friendly
                                          • Air conditioning

                                          Price per night from

                                          $1,036

                                          Responds fast!
                                          avg. 3 hours 32 minutes

                                          Price per night from

                                          $1,036

                                          Distance approx 0.1 km from Grassy Key

                                          (1) Very Good 

                                            12

                                            4BR Waterfront Retreat-Tiki-Jacuzzi-Dock

                                            Marathon / Marathon Shores

                                            Marathon Shores house

                                            4 10 7 nights min

                                            • 4 bedrooms
                                            • sleeps 10
                                            • 7 nights min
                                            • Child Friendly
                                            • Pet Friendly

                                            Price per night from

                                            $360

                                            Price per night from

                                            $360

                                            Distance approx 2.06 km from Grassy Key

                                              49

                                              P03 ~ Water Wonderland Marathon ~ Coco Plum 4 Bedroom

                                              Florida Keys / Marathon

                                              Marathon house

                                              4 8 7 nights min

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

                                              Price per night from

                                              $323

                                              Price per night from

                                              $323

                                              Distance approx 8.82 km from Grassy Key

                                              (8) Very Good 

                                              Certificate of Excellence

                                                12

                                                DECEMBER 18 THROUGH 26TH AVAILABLE

                                                Florida Keys / Duck Key

                                                Duck Key villa

                                                2 6 min stay varies

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

                                                Certificate of Excellence

                                                Price per night from

                                                $230

                                                Responds fast!
                                                avg. 28 minutes

                                                Price per night from

                                                $230

                                                Distance approx 3.08 km from Grassy Key

                                                  28

                                                  RENOVATED 2 BED MARATHON TOWNHOME w/ DOCK SPACE - WALK TO BEACH!

                                                  Marathon / Marathon Shores

                                                  Marathon Shores townhouse

                                                  2 4 28 nights min

                                                  • 2 bedrooms
                                                  • sleeps 4
                                                  • 28 nights min
                                                  • Nearest beach 0.1 mi
                                                  • Swimming pool
                                                  • Air conditioning

                                                  Price per night from

                                                  $333

                                                  Price per night from

                                                  $333

                                                  Distance approx 8.8 km from Grassy Key

                                                  (1) Excellent 

                                                    26

                                                    Waterfront fun and funky , Beautiful Duck Key

                                                    Florida Keys / Duck Key

                                                    Duck Key condo

                                                    1 4 min stay varies

                                                    • 1 bedroom
                                                    • sleeps 4
                                                    • min stay varies
                                                    • Nearest beach 5 mi
                                                    • Air conditioning

                                                    Price per night from

                                                    $172

                                                    Price per night from

                                                    $172

                                                    Distance approx 2.86 km from Grassy Key

                                                      9

                                                      Sombrero Beach, canal front home with pool!

                                                      Florida Keys / Marathon

                                                      Marathon house

                                                      3 6 6 nights min

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

                                                      Price per night from

                                                      $460

                                                      Responds fast!
                                                      avg. 1 hour 33 minutes

                                                      Price per night from

                                                      $460

                                                      Distance approx 13.84 km from Grassy Key

                                                      (21) Excellent 

                                                        53

                                                        CHARMING KCB POOL COTTAGE, PVT POOL,46 FT DCK,WIFI

                                                        Florida Keys / Key Colony Beach

                                                        Key Colony Beach cottage

                                                        2 4 7 nights min

                                                        • 2 bedrooms
                                                        • sleeps 4
                                                        • 7 nights min
                                                        • Beach / lakeside relaxation
                                                        • Swimming pool
                                                        • Child Friendly
                                                        “Most wonderful vacation home ever.” The pool, the hammock, the dock, the decor....it was the best place i have ever stayed. I didnt want to leave. Laying in the hammock every night listening to the palm trees swaying in the breeze. Watching the snook
                                                        …see more

                                                        Price per night from

                                                        $201

                                                        Price per night from

                                                        $201

                                                        Distance approx 1.65 km from Grassy Key

                                                        (1) Excellent 

                                                          31

                                                          P24 Key Colony Bungalow

                                                          Florida Keys / Key Colony Beach

                                                          Key Colony Beach house

                                                          3 6 7 nights min

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

                                                          Price per night from

                                                          $180

                                                          Price per night from

                                                          $180

                                                          Distance approx 1.17 km from Grassy Key

                                                            37

                                                            LUXURY OCEAN FRONT w/PRIVATE ELEVATOR/BOAT DOCK

                                                            Marathon / Marathon Shores

                                                            Marathon Shores house

                                                            3 8 7 nights min

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

                                                            Price per night from

                                                            $459

                                                            Responds fast!
                                                            avg. 56 minutes

                                                            Price per night from

                                                            $459

                                                            Distance approx 1.12 km from Grassy Key

                                                            (1) Very Good 

                                                              24

                                                              3BD, 2BA, Pool, Waterfront Canal.WIFI +Cabana Club Pool/Beach! 70' seawall

                                                              Florida Keys / Key Colony Beach

                                                              Key Colony Beach house

                                                              3 7 7 nights min

                                                              • 3 bedrooms
                                                              • sleeps 7
                                                              • 7 nights min
                                                              • Nearest beach 1 mi
                                                              • Swimming pool
                                                              • Child Friendly

                                                              Price per night from

                                                              $317

                                                              Responds fast!
                                                              avg. 1 hour 50 minutes

                                                              Price per night from

                                                              $317

                                                              Distance approx 2.34 km from Grassy Key

                                                              (5) Excellent 

                                                                18

                                                                Outstanding Oceanfront Condo on the Beach!!

                                                                Florida Keys / Marathon

                                                                Marathon condo

                                                                2 6 7 nights min

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

                                                                Price per night from

                                                                $237

                                                                Responds fast!
                                                                avg. 2 hours 42 minutes

                                                                Price per night from

                                                                $237

                                                                Distance approx 1.2 km from Grassy Key

                                                                (1) Excellent 

                                                                  43

                                                                  P44 4 bdm Gulf Side Estate w/ private pool

                                                                  Florida Keys / Marathon

                                                                  Marathon house

                                                                  4 8 7 nights min

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

                                                                  Price per night from

                                                                  $323

                                                                  Price per night from

                                                                  $323

                                                                  Distance approx 13.27 km from Grassy Key

                                                                    17

                                                                    Florida Keys Oceanfront Paradise

                                                                    Florida Keys / Long Key

                                                                    Long Key apartment

                                                                    3 8 30 nights min

                                                                    • 3 bedrooms
                                                                    • sleeps 8
                                                                    • 30 nights min
                                                                    • Beach / lakeside relaxation
                                                                    • Child Friendly
                                                                    • Air conditioning

                                                                    Price per night from

                                                                    $192

                                                                    Price per night from

                                                                    $192

                                                                    Distance approx 1.88 km from Grassy Key

                                                                      4

                                                                      Paradise

                                                                      Florida Keys / Key Colony Beach

                                                                      Key Colony Beach condo

                                                                      2 4 14 nights min

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

                                                                      Price per night from

                                                                      $171

                                                                      Price per night from

                                                                      $171

                                                                      Distance approx 4.24 km from Grassy Key

                                                                        4

                                                                        Outstanding 5-star rating resort

                                                                        Marathon / Marathon Shores

                                                                        Marathon Shores villa

                                                                        1 4 2 nights min

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

                                                                        Price per night from

                                                                        $288

                                                                        Price per night from

                                                                        $288

                                                                        Distance approx 3.01 km from Grassy Key

                                                                          21

                                                                          Cozy Condo Hat # 205

                                                                          Florida Keys / Marathon

                                                                          Marathon apartment

                                                                          1 4 3 nights min

                                                                          • 1 bedroom
                                                                          • sleeps 4
                                                                          • 3 nights min
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Car not necessary

                                                                          Price per night from

                                                                          $133

                                                                          Price per night from

                                                                          $133

                                                                          Distance approx 1.9 km from Grassy Key

                                                                            21

                                                                            Sunny Yacht Club Townhome

                                                                            Florida Keys / Key Colony Beach

                                                                            Key Colony Beach townhouse

                                                                            3 8 7 nights min

                                                                            • 3 bedrooms
                                                                            • sleeps 8
                                                                            • 7 nights min
                                                                            • Swimming pool
                                                                            • Child Friendly
                                                                            • Car not necessary

                                                                            Price per night from

                                                                            $199

                                                                            Price per night from

                                                                            $199

                                                                            Distance approx 0.1 km from Grassy Key

                                                                            (11) Excellent 

                                                                              86

                                                                              Private Island Rental with 19' Boat, Seabird Key

                                                                              Florida Keys / Marathon

                                                                              Marathon house

                                                                              3 8 7 nights min

                                                                              • 3 bedrooms
                                                                              • sleeps 8
                                                                              • 7 nights min
                                                                              • Beach / lakeside relaxation
                                                                              • Nearest beach 0 mi
                                                                              • Child Friendly
                                                                              “Heaven On Earth!” From the moment you step foot on this beautiful island paradise, you'll feel like you've been transported to your own little private world! Every amenity has been thought of from an outstanding outdoor kitchen, complete with state o
                                                                              …see more

                                                                              Price per night from

                                                                              $1,313

                                                                              Price per night from

                                                                              $1,313