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536 Houses

    54

    Oceanfront duplex with spectacular views, beach, and dock

    Florida Keys / Long Key

    Long Key house

    2 6 5 nights min

    • 2 bedrooms
    • sleeps 6
    • 5 nights min
    • Child Friendly
    • Car not necessary
    • Air conditioning

    Price per night from

    $344

    Responds fast!
    avg. 2 hours 26 minutes

    Price per night from

    $344

      26

      Bay Harbour D114

      Florida Keys / Long Key

      Long Key house

      3 8 7 nights min

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

      Price per night from

      $328

      Price per night from

      $328

        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

        (1) Excellent 

          0

          Oceanfront duplex with beautiful beach and dock for boat access! Dogs OK!

          Florida Keys / Long Key

          Long Key house

          2 6 5 nights min

          • 2 bedrooms
          • sleeps 6
          • 5 nights min
          • Child Friendly
          • Car not necessary
          • Air conditioning

          Price per night from

          $344

          Responds fast!
          avg. 3 hours 4 minutes

          Price per night from

          $344

            75

            Dog-friendly, oceanfront duplex with private beach access & dock!

            Long Key / Layton

            Layton house

            4 8 min stay varies

            • 4 bedrooms
            • sleeps 8
            • min stay varies
            • Child Friendly
            • Car not necessary
            • Air conditioning

            Price per night from

            $687

            Responds fast!
            avg. 2 hours 26 minutes

            Price per night from

            $687

            (12) Very Good 

              47

              Bay Harbour A-304- 7 night minimum

              Florida Keys / Long Key

              Long Key house

              3 6 7 nights min

              • 3 bedrooms
              • sleeps 6
              • 7 nights min
              • Child Friendly
              “Perfect” Stayed here for over a week to go fishing with the family. I would say its the perfect place to stay if you want to fish the keys. We rented a boat at Bud and Mary's and it was delivered right to the units slip. Bait and fuel is available
              …see more

              Price per night from

              $328

              Price per night from

              $328

                24

                Oceanfront 2BR w/ Private Beach – Close to Top-Rated Scuba & Snorkeling

                Florida Keys / Long Key

                Long Key house

                2 4 30 nights min

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

                Price per night from

                $175

                Price per night from

                $175

                  27

                  48 West Plaza Del Lago

                  Florida Keys / Long Key

                  Long Key house

                  3 7 28 nights min

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

                  Price per night from

                  $172

                  Price per night from

                  $172

                    24

                    Oceanside 3BR Condo w/ Heated Pool, Spa, Tennis, Boat Slips & Rooftop Balcony

                    Long Key / Layton

                    Layton apartment

                    3 8 7 nights min

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

                    Price per night from

                    $504

                    Price per night from

                    $504

                      10

                      135 Gulfview Drive

                      Florida Keys / Long Key

                      Long Key house

                      2 4 28 nights min

                      • 2 bedrooms
                      • sleeps 4
                      • 28 nights min
                      • Child Friendly

                      Price per night from

                      $115

                      Price per night from

                      $115

                        19

                        220 Costa Bravo Drive

                        Long Key / Layton

                        Layton house

                        3 6 min stay varies

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

                        Price per night from

                        $229

                        Price per night from

                        $229

                          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

                            50

                            NEW LISTING! Relaxing, waterfront retreat w/boat dock & amazing ocean views

                            Long Key / Layton

                            Layton house

                            3 8 28 nights min

                            • 3 bedrooms
                            • sleeps 8
                            • 28 nights min
                            • Child Friendly
                            • Car not necessary
                            • Air conditioning

                            Price per night from

                            $281

                            Responds fast!
                            avg. 3 hours 4 minutes

                            Price per night from

                            $281

                              44

                              A Pirates Great Escape ~ 3bed/2baths Ocean View Slip Not Available

                              Long Key / Layton

                              Layton condo

                              3 8 7 nights min

                              • 3 bedrooms
                              • sleeps 8
                              • 7 nights min
                              • Ask about children

                              Price per night from

                              $409

                              Price per night from

                              $409

                                24

                                NEW! Scenic 3BR Islamorada House w/Canal Views!

                                Florida Keys / Long Key

                                Long Key house

                                3 8 min stay varies

                                • 3 bedrooms
                                • sleeps 8
                                • min stay varies
                                • Beach / lakeside relaxation
                                • Child Friendly
                                • Air conditioning
                                Inquire for Rates

                                Responds fast!
                                avg. 58 minutes

                                Inquire for Rates
                                  24

                                  Welcome to Paradise

                                  Florida Keys / Long Key

                                  Long Key townhouse

                                  2 5 30 nights min

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

                                  Price per night from

                                  $205

                                  Price per night from

                                  $205

                                    22

                                    108 W. Plaza Del Sol

                                    Florida Keys / Long Key

                                    Long Key house

                                    3 4 28 nights min

                                    • 3 bedrooms
                                    • sleeps 4
                                    • 28 nights min
                                    • Swimming pool
                                    • Child Friendly

                                    Price per night from

                                    $153

                                    Price per night from

                                    $153

                                      13

                                      132 Atlantic Lane

                                      Long Key / Layton

                                      Layton house

                                      2 6 28 nights min

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

                                      Price per night from

                                      $153

                                      Price per night from

                                      $153

                                      Great rentals within 20 miles that match your search

                                      Distance approx 13.18 km from Long Key

                                      (2) Excellent 

                                        21

                                        Ocean-Front Caribbean Home.

                                        Florida Keys / Islamorada

                                        Islamorada house

                                        3 8 2 nights min

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

                                        Price per night from

                                        $1,506

                                        Price per night from

                                        $1,506

                                        Distance approx 15.13 km from Long 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 14.97 km from Long 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 15.24 km from Long 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 17.16 km from Long Key

                                              (6) Very Good 

                                                14

                                                THE PERFECT GETAWAY

                                                Florida Keys / Islamorada

                                                Islamorada house

                                                4 10 7 nights min

                                                • 4 bedrooms
                                                • sleeps 10
                                                • 7 nights min
                                                • Beach / lakeside relaxation
                                                • Child Friendly
                                                • Air conditioning
                                                “The owner was understanding and worked with us” I was scheduled to rent from Dec 29th to Jan 4th and expected 7 friends to join me. For multiple personal reasons four of the seven had to back out and it is not the place you want to be without the full
                                                …see more

                                                Price per night from

                                                $411

                                                Price per night from

                                                $411

                                                Distance approx 15.17 km from Long 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 18.95 km from Long 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 6.85 km from Long Key Show on Map

                                                      51

                                                      Islamorada Paradise

                                                      Florida Keys / Islamorada

                                                      Islamorada house

                                                      3 6 30 nights min

                                                      • 3 bedrooms
                                                      • sleeps 6
                                                      • 30 nights min
                                                      • Swimming pool
                                                      • Air conditioning
                                                      • Private garden

                                                      Price per night from

                                                      $687

                                                      Price per night from

                                                      $687

                                                      Distance approx 15.13 km from Long 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 18.86 km from Long 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 18.81 km from Long 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 16.27 km from Long Key

                                                              26

                                                              Islamorada Oceanfront Home In Anglers Reef Ocean Views, Dock, Comm Pool & Beach

                                                              Florida Keys / Islamorada

                                                              Islamorada house

                                                              2 6 7 nights min

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

                                                              Price per night from

                                                              $525

                                                              Price per night from

                                                              $525

                                                              Distance approx 7.07 km from Long 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 7.09 km from Long 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 14.73 km from Long 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 14.41 km from Long 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 5.55 km from Long Key Show on Map

                                                                        29

                                                                        Recently Remodeled Beautiful Pool Home with Private Dock with Beach Access

                                                                        Florida Keys / Islamorada

                                                                        Islamorada house

                                                                        4 8 30 nights min

                                                                        • 4 bedrooms
                                                                        • sleeps 8
                                                                        • 30 nights min
                                                                        • Child Friendly
                                                                        • Pet Friendly

                                                                        Price per night from

                                                                        $288

                                                                        Price per night from

                                                                        $288

                                                                        Distance approx 5.04 km from Long Key Show on Map

                                                                          22

                                                                          7 Bed, 6 Bath resort-like pool home. Boat dockage. Pets. Great for large groups!

                                                                          Florida Keys / Islamorada

                                                                          Islamorada house

                                                                          7 14 30 nights min

                                                                          • 7 bedrooms
                                                                          • sleeps 14
                                                                          • 30 nights min
                                                                          • Nearest beach 1 mi
                                                                          • Swimming pool
                                                                          • Child Friendly

                                                                          Price per night from

                                                                          $460

                                                                          Price per night from

                                                                          $460

                                                                          Distance approx 5.55 km from Long Key Show on Map

                                                                            25

                                                                            Lower Mat Canal Front Home w/ 60' dock and access to private beach on the bay!

                                                                            Florida Keys / Islamorada

                                                                            Islamorada house

                                                                            3 8 30 nights min

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

                                                                            Price per night from

                                                                            $153

                                                                            Price per night from

                                                                            $153

                                                                            Distance approx 15.16 km from Long 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