Vacation Rentals & Apartments in Cudjoe Key

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85 apartments

(1) Very Good 

    11

    Magnificent Ocean view with 35' dock , Canal home in gated Venture Out Resort

    Florida Keys / Cudjoe Key

    Cudjoe Key cottage

    2 6 3 nights min

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

    Price per night from

    $184

    Price per night from

    $184

    (15) Very Good 

      28

      Family Retreat ocean front home with private pool

      Florida Keys / Cudjoe Key

      Cudjoe Key house

      6 18 7 nights min

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

      Price per night from

      $571

      Price per night from

      $571

        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

        $142

        Responds fast!
        avg. 3 hours 16 minutes

        Price per night from

        $142

        (10) Excellent 

          26

          Tropical Paradise Oceanfront Home with Pool

          Florida Keys / Cudjoe Key

          Cudjoe Key house

          2 6 7 nights min

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

          Price per night from

          $400

          Price per night from

          $400

          (1) Excellent 

            12

            Family Friendly 2 Bedroom 1 Bath, 32' Seawall, 4 Bikes, 2 Kayaks and padl board

            Florida Keys / Cudjoe Key

            Cudjoe Key caravan/mobile home

            2 6 3 nights min

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

            Price per night from

            $155

            Price per night from

            $155

            (12) Excellent 

              30

              Fandango

              Florida Keys / Cudjoe Key

              Cudjoe Key house

              5 14 7 nights min

              • 5 bedrooms
              • sleeps 14
              • 7 nights min
              • Beach / lakeside relaxation
              • Nearest beach 13 mi
              • Swimming pool

              Price per night from

              $571

              Price per night from

              $571

                13

                Paradise on Cudjoe Bay

                Florida Keys / Cudjoe Key

                Cudjoe Key house

                2 6 min stay varies

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

                Price per night from

                $310

                Responds fast!
                avg. 2 hours 16 minutes

                Price per night from

                $310

                (2) Excellent 

                  34

                  Oksana's Tropical Beach Oasis

                  Florida Keys / Cudjoe Key

                  Cudjoe Key house

                  4 14 7 nights min

                  • 4 bedrooms
                  • sleeps 14
                  • 7 nights min
                  • Nearest beach 10 mi
                  • Swimming pool
                  • Child Friendly

                  Price per night from

                  $600

                  Price per night from

                  $600

                    14

                    Hogfish Retreat

                    Florida Keys / Cudjoe Key

                    Cudjoe Key house

                    2 6 28 nights min

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

                    Price per night from

                    $194

                    Price per night from

                    $194

                    (3) Very Good 

                      19

                      Charming 3bedroom/2bath home in the Florida Keys

                      Florida Keys / Cudjoe Key

                      Cudjoe Key house

                      3 6 30 nights min

                      • 3 bedrooms
                      • sleeps 6
                      • 30 nights min
                      • Beach / lakeside relaxation
                      • Child Friendly
                      • Air conditioning

                      Price per night from

                      $106

                      Price per night from

                      $106

                        28

                        Tropical Canal Home

                        Florida Keys / Cudjoe Key

                        Cudjoe Key house

                        3 6 30 nights min

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

                        Price per night from

                        $192

                        Price per night from

                        $192

                        (3) Excellent 

                          34

                          Blue Palms Retreat (formerly known as Heron's Roost)

                          Florida Keys / Cudjoe Key

                          Cudjoe Key house

                          3 8 7 nights min

                          • 3 bedrooms
                          • sleeps 8
                          • 7 nights min
                          • Nearest beach 10 mi
                          • Swimming pool
                          • Child Friendly

                          Price per night from

                          $457

                          Price per night from

                          $457

                            18

                            Yellow weekly vacation home, great location. Heated private pool.

                            Florida Keys / Cudjoe Key

                            Cudjoe Key house

                            3 6 7 nights min

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

                            Price per night from

                            $393

                            Price per night from

                            $393

                            (2) Very Good 

                              29

                              Tropical Blue Adventure Waterfront at Venture Out

                              Florida Keys / Cudjoe Key

                              Cudjoe Key house

                              2 6 3 nights min

                              • 2 bedrooms
                              • sleeps 6
                              • 3 nights min
                              • Beach / lakeside relaxation
                              • Nearest beach 30 mi
                              • Swimming pool

                              Price per night from

                              $229

                              Price per night from

                              $229

                              Great rentals within 20 miles that match your search

                              Distance approx 0.1 km from Cudjoe Key

                              (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

                                $204

                                Price per night from

                                $204

                                Distance approx 19.23 km from Cudjoe Key

                                (49) Very Good 

                                  291

                                  Real World MTV House Key West

                                  Florida Keys / Key West

                                  Key West house

                                  10 22 min stay varies

                                  • 10 bedrooms
                                  • sleeps 22
                                  • min stay varies
                                  • Beach / lakeside relaxation
                                  • Swimming pool
                                  • Child Friendly
                                  “Haha Buffalo, New York” This year while my friends and neighbors froze to death in Buffalo, my extended family and a few friends escaped the cold at the Real World MTV House in Key West. It was cold in Key West as well just 78 degrees, all the locals
                                  …see more

                                  Price per night from

                                  $1,783

                                  Responds fast!
                                  avg. 2 hours 42 minutes

                                  Price per night from

                                  $1,783

                                  Distance approx 5.95 km from Cudjoe Key

                                    24

                                    Sunrise Drive

                                    Florida Keys / Big Pine Key

                                    Big Pine Key house

                                    3 8 min stay varies

                                    • 3 bedrooms
                                    • sleeps 8
                                    • min stay varies
                                    • Beach / lakeside relaxation
                                    • Nearest beach 8 mi
                                    • Suitable for children age 5+

                                    Price per night from

                                    $197

                                    Responds fast!
                                    avg. 3 hours 4 minutes

                                    Price per night from

                                    $197

                                    Distance approx 5.27 km from Cudjoe Key

                                      13

                                      3 bedroom canal front home minutes from open Water!

                                      Florida Keys / Big Pine Key

                                      Big Pine Key house

                                      3 10 30 nights min

                                      • 3 bedrooms
                                      • sleeps 10
                                      • 30 nights min
                                      • Child Friendly
                                      • Air conditioning
                                      • Private garden

                                      Price per night from

                                      $171

                                      Responds fast!
                                      avg. 3 hours 41 minutes

                                      Price per night from

                                      $171

                                      Distance approx 5.06 km from Cudjoe Key

                                      (1) Excellent 

                                        20

                                        Fisherman's Paradise in the Heart of Big Pine Key

                                        Florida Keys / Big Pine Key

                                        Big Pine Key house

                                        3 6 30 nights min

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

                                        Price per night from

                                        $113

                                        Responds fast!
                                        avg. 2 hours 20 minutes

                                        Price per night from

                                        $113

                                        Distance approx 5.25 km from Cudjoe Key

                                          16

                                          New Listing! Beautiful Canal front , Key Deer and jacuzzi.

                                          Florida Keys / Big Pine Key

                                          Big Pine Key house

                                          3 8 28 nights min

                                          • 3 bedrooms
                                          • sleeps 8
                                          • 28 nights min
                                          • Child Friendly
                                          • Air conditioning
                                          • Pet Friendly

                                          Price per night from

                                          $171

                                          Price per night from

                                          $171

                                          Distance approx 19.06 km from Cudjoe Key

                                          (1) Excellent 

                                            9

                                            Key West Living-Oceanside Catamaran Wind Spirit

                                            Florida Keys / Key West

                                            Key West yacht

                                            3 6 3 nights min

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

                                            Price per night from

                                            $398

                                            Price per night from

                                            $398

                                            Distance approx 19.52 km from Cudjoe Key

                                            (8) Excellent 

                                              32

                                              New Listing Family Friendly

                                              Florida Keys / Key West

                                              Key West townhouse

                                              3 6 3 nights min

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

                                              Price per night from

                                              $365

                                              Responds fast!
                                              avg. 28 minutes

                                              Price per night from

                                              $365

                                              Distance approx 19.55 km from Cudjoe Key

                                              (1) Excellent 

                                                12

                                                Comfy Family Home in a Gorgeous Gated Community

                                                Florida Keys / Key West

                                                Key West townhouse

                                                3 6 3 nights min

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

                                                Price per night from

                                                $341

                                                Responds fast!
                                                avg. 28 minutes

                                                Price per night from

                                                $341

                                                Distance approx 0.1 km from Cudjoe Key Show on Map

                                                  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

                                                  $159

                                                  Responds fast!
                                                  avg. 3 hours 44 minutes

                                                  Price per night from

                                                  $159

                                                  Distance approx 5.45 km from Cudjoe Key

                                                    35

                                                    Caribbean Cove

                                                    Florida Keys / Big Pine Key

                                                    Big Pine Key house

                                                    2 9 28 nights min

                                                    • 2 bedrooms
                                                    • sleeps 9
                                                    • 28 nights min
                                                    • Child Friendly
                                                    • Air conditioning
                                                    • Private garden

                                                    Price per night from

                                                    $98

                                                    Responds fast!
                                                    avg. 3 hours 17 minutes

                                                    Price per night from

                                                    $98

                                                    Distance approx 19.11 km from Cudjoe Key

                                                      10

                                                      Atlantis Dream Escape

                                                      Florida Keys / Key West

                                                      Key West house

                                                      3 8 30 nights min

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

                                                      Price per night from

                                                      $323

                                                      Price per night from

                                                      $323

                                                      Distance approx 5.82 km from Cudjoe Key

                                                        28

                                                        Florida Keys Fisherman and Divers Paradise

                                                        Florida Keys / Big Pine Key

                                                        Big Pine Key house

                                                        4 12 30 nights min

                                                        • 4 bedrooms
                                                        • sleeps 12
                                                        • 30 nights min
                                                        • Swimming pool
                                                        • Child Friendly
                                                        • Air conditioning

                                                        Price per night from

                                                        $285

                                                        Price per night from

                                                        $285

                                                        Distance approx 4.61 km from Cudjoe Key

                                                          16

                                                          Sparkling canalfront house surrounded by palms

                                                          Florida Keys / Big Pine Key

                                                          Big Pine 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

                                                          $134

                                                          Price per night from

                                                          $134

                                                          Distance approx 2.05 km from Cudjoe Key Show on Map

                                                            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

                                                            $143

                                                            Price per night from

                                                            $143

                                                            Distance approx 7.85 km from Cudjoe Key

                                                              11

                                                              The Key's only real beach house Dock and pool

                                                              Florida Keys / Key West

                                                              Key West house

                                                              2 4 7 nights min

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

                                                              Price per night from

                                                              $392

                                                              Price per night from

                                                              $392

                                                              Distance approx 7.63 km from Cudjoe 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

                                                                $341

                                                                Price per night from

                                                                $341

                                                                Distance approx 6.91 km from Cudjoe Key

                                                                  8

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

                                                                  Florida Keys / Key West

                                                                  Key West house

                                                                  3 6 7 nights min

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

                                                                  Price per night from

                                                                  $531

                                                                  Price per night from

                                                                  $531

                                                                  Distance approx 7.05 km from Cudjoe 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

                                                                    $736

                                                                    Price per night from

                                                                    $736

                                                                    Distance approx 6.87 km from Cudjoe Key

                                                                    (4) Excellent 

                                                                      11

                                                                      Key West's only Real Beach House

                                                                      Florida Keys / Key West

                                                                      Key West guest house

                                                                      2 4 7 nights min

                                                                      • 2 bedrooms
                                                                      • sleeps 4
                                                                      • 7 nights min
                                                                      • Beach / lakeside relaxation
                                                                      • Swimming pool
                                                                      • Ask about children

                                                                      Price per night from

                                                                      $391

                                                                      Price per night from

                                                                      $391

                                                                      Distance approx 19.51 km from Cudjoe Key

                                                                      (2) Excellent 

                                                                        70

                                                                        Spacious 3BR/3BA Catamaran as Private Sailing Charter up to 7 nights in Key West

                                                                        Florida Keys / Key West

                                                                        Key West yacht

                                                                        3 6 1 night min

                                                                        • 3 bedrooms
                                                                        • sleeps 6
                                                                        • 1 night min
                                                                        • Child Friendly
                                                                        • Air conditioning

                                                                        Price per night from

                                                                        $2,439

                                                                        Price per night from

                                                                        $2,439

                                                                        Distance approx 19.07 km from Cudjoe Key

                                                                          17

                                                                          Reduced Rate! New 46' Sailing Yacht & Other Boats

                                                                          Florida Keys / Stock Island

                                                                          Stock Island yacht

                                                                          3 8 2 nights min

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

                                                                          Price per night from

                                                                          $312

                                                                          Responds fast!
                                                                          avg. 2 hours 13 minutes

                                                                          Price per night from

                                                                          $312

                                                                          Distance approx 2.48 km from Cudjoe Key

                                                                          (5) Very Good 

                                                                            13

                                                                            Oceanfront Home Rental in Ramrod Key, Florida

                                                                            Florida Keys / Ramrod Key

                                                                            Ramrod Key house

                                                                            3 6 30 nights min

                                                                            • 3 bedrooms
                                                                            • sleeps 6
                                                                            • 30 nights min
                                                                            • Beach / lakeside relaxation
                                                                            • Child Friendly
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $93

                                                                            Price per night from

                                                                            $93

                                                                            Distance approx 6.85 km from Cudjoe Key

                                                                              16

                                                                              Private beach estate.Dock and pool.

                                                                              Florida Keys / Key West

                                                                              Key West house

                                                                              3 6 30 nights min

                                                                              • 3 bedrooms
                                                                              • sleeps 6
                                                                              • 30 nights min
                                                                              • Nearest beach 0 mi
                                                                              • Swimming pool
                                                                              • Child Friendly

                                                                              Price per night from

                                                                              $281

                                                                              Price per night from

                                                                              $281

                                                                              About Cudjoe Key

                                                                              Looking for a relaxed break? Look no further than Cudjoe Key in Florida. With property rentals lining the long strip of beach, you'll never be far away from white sands and turquoise seas. Sound like your idea of heaven? You can book property rentals in Cudjoe Key with FlipKey today.

                                                                              About Cudjoe Key

                                                                              With a tiny population of just over 1600 residents, Cudjoe Key is the ideal getaway if you're looking for a relaxing vacation.

                                                                              Originally called Littleton Island, this quiet resort is located on an island in Florida Keys. It's perfect for those wishing to become closer to nature, with the intention to get away from the hustle and bustle of everyday life! Here, you can sit on the beach and expect to see tropical sunsets at dusk or have a splash in the ocean.

                                                                              Many use Cudjoe Key as a stop off to travel to other nearby destinations, therefore this resort is a perfect weekend resort. In just over 73 miles, you will reach Key Largo and, in just over two hours, you will arrive in the more commercialized resort of Miami, where you can experience a more active atmosphere with a wide array of activities and entertainment.

                                                                              What to do

                                                                              Cudjoe Key offers a wide range of activities, however may revolve around watersports and activities due to the wide stretch of beach and fantastic waves. Snorkeling and diving are perhaps the most popular with tourists, especially those who are looking for a taste of adventure on their trip.

                                                                              Alternatively, if you're looking for more challenging activities, why not try your hand at kayaking and canoeing? You’ll find yourself traveling down water channels surrounding nearby islands – ideal for both beginners and the more advanced.

                                                                              Those who aren't into extreme sports may prefer chilled out boat trips which can be rented for private use, or you may decide to join a fishing trip around the island and pull in your own catch! Most fishing trips contain guides so you have all the information you need. 

                                                                              Top Cudjoe Key travel tips

                                                                              The weather in Cudjoe Key stays regular all year round and during the summer months of July and August, temperatures average at around 28 degrees Celsius, while during the winter months may drop to only 24 degrees Celsius. This makes Cudjoe Key a great destination for all year round.

                                                                              Many tourists hire their own vehicle when traveling to Cudjoe Key because most activity takes place outside of the resort. Cudjoe Key has its own restaurants and small individual shops, but sorting your own transport would be an essential aspect of your visit to get around.

                                                                              If you're looking for a relaxed vacation, away from the bustle of normal life, Cudjoe Key is a great choice. With larger resorts just a car drive away, you'll be away from the commercial life, but close enough to experience it should you decide. Book your Cudjoe Key vacation rental with FlipKey today!