Vacation Rentals with Pool in Cudjoe Key

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Filtering by: Swimming pool

53 vacation rentals

(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

    (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

      $156

      Price per night from

      $156

        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

        $311

        Responds fast!
        avg. 2 hours 16 minutes

        Price per night from

        $311

        (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

          $402

          Price per night from

          $402

          (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

            (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

              $602

              Price per night from

              $602

              (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

                $460

                Price per night from

                $460

                  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

                    $230

                    Price per night from

                    $230

                    Great rentals within 20 miles that match your search

                    Distance approx 19.22 km from Cudjoe Key

                    (19) Excellent 

                      26

                      Spectacular Atlantic Ocean View Condo (MONTHLY)

                      Florida Keys / Key West

                      Key West apartment

                      2 6 28 nights min

                      • 2 bedrooms
                      • sleeps 6
                      • 28 nights min
                      • Beach / lakeside relaxation
                      • Swimming pool
                      • Child Friendly
                      “Amazing Views And A Great Condo” My wife and I stayed here on our honeymoon and were absolutely 100% pleased with the condo. I have to honestly say it was the nicest condo either of us have stayed in. The view was amazing and the patio was very tranqu
                      …see more

                      Price per night from

                      $330

                      Price per night from

                      $330

                      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

                        $206

                        Price per night from

                        $206

                        Distance approx 3.57 km from Cudjoe Key Show on Map

                        (1) Excellent 

                          25

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

                          Lower Keys / Summerland Key

                          Summerland Key house

                          4 8 7 nights min

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

                          Price per night from

                          $395

                          Price per night from

                          $395

                          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

                            $1,799

                            Responds fast!
                            avg. 2 hours 52 minutes

                            Price per night from

                            $1,799

                            Distance approx 19.58 km from Cudjoe Key

                            (3) Average 

                              0

                              Newly remodeled family home with a shared swimming pool and fitness center!

                              Florida Keys / Key West

                              Key West house

                              3 6 min stay varies

                              • 3 bedrooms
                              • sleeps 6
                              • min stay varies
                              • Swimming pool
                              • Child Friendly
                              • Car not necessary
                              “Cute place” Excellent home and a gated community with great amenities. Exercise room and gated pool are clean and well kept.
                              …see more

                              Price per night from

                              $269

                              Price per night from

                              $269

                              Distance approx 0.1 km from Cudjoe Key

                                0

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

                                Lower Keys / Summerland Key

                                Summerland Key house

                                3 6 28 nights min

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

                                Price per night from

                                $201

                                Price per night from

                                $201

                                Distance approx 3.58 km from Cudjoe Key

                                (1) Excellent 

                                  13

                                  florida keys vacation rental

                                  Lower Keys / Little Torch Key

                                  Little Torch Key house

                                  3 10 5 nights min

                                  • 3 bedrooms
                                  • sleeps 10
                                  • 5 nights min
                                  • Nearest beach 24 mi
                                  • Swimming pool
                                  • Child Friendly

                                  Price per night from

                                  $700

                                  Price per night from

                                  $700

                                  Distance approx 19.75 km from Cudjoe Key

                                  (1) Excellent 

                                    24

                                    Isle Of View II

                                    Florida Keys / Key West

                                    Key West boathouse

                                    2 6 min stay varies

                                    • 2 bedrooms
                                    • sleeps 6
                                    • min stay varies
                                    • Nearest beach 6 mi
                                    • Swimming pool
                                    • Child Friendly

                                    Price per night from

                                    $228

                                    Responds fast!
                                    avg. 2 hours 45 minutes

                                    Price per night from

                                    $228

                                    Distance approx 19.83 km from Cudjoe Key

                                      16

                                      NEW LISTING! 40’ Luxury Catamaran Yacht!

                                      Florida Keys / Key West

                                      Key West yacht

                                      3 7 3 nights min

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

                                      Price per night from

                                      $1,259

                                      Responds fast!
                                      avg. 57 minutes

                                      Price per night from

                                      $1,259

                                      Distance approx 19.06 km from Cudjoe Key

                                      (2) 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

                                        $401

                                        Price per night from

                                        $401

                                        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

                                          $343

                                          Responds fast!
                                          avg. 28 minutes

                                          Price per night from

                                          $343

                                          Distance approx 19.54 km from Cudjoe Key

                                          (67) Very Good 

                                            30

                                            Tee by the Sea - NO DAMAGE FROM HURRICANE IRMA , Plus 7 Bikes FREE

                                            Florida Keys / Key West

                                            Key West apartment

                                            2 6 min stay varies

                                            • 2 bedrooms
                                            • sleeps 6
                                            • min stay varies
                                            • Beach / lakeside relaxation
                                            • Nearest beach 3 mi
                                            • Swimming pool
                                            “Absolutely Perfect!!!” I chose this place to rent because it looked nice and it was affordable. I knew going in that it was not located on the Key West island, which was fine considering the condo came with bikes you could ride onto the island...What
                                            …see more

                                            Price per night from

                                            $276

                                            Responds fast!
                                            avg. 2 hours 35 minutes

                                            Price per night from

                                            $276

                                            Distance approx 19.05 km from Cudjoe Key

                                              14

                                              Catchin' Moments Charters

                                              Florida Keys / Key West

                                              Key West yacht

                                              4 8 3 nights min

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

                                              Price per night from

                                              $1,093

                                              Price per night from

                                              $1,093

                                              Distance approx 0.1 km from Cudjoe Key

                                              (1) Excellent 

                                                51

                                                Oceanfront House

                                                Lower Keys / Summerland Key

                                                Summerland Key house

                                                3 8 30 nights min

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

                                                Price per night from

                                                $422

                                                Responds fast!
                                                avg. 3 hours 43 minutes

                                                Price per night from

                                                $422

                                                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

                                                  $288

                                                  Price per night from

                                                  $288

                                                  Distance approx 9.97 km from Cudjoe Key

                                                    0

                                                    Spectacular, oceanfront, dog-friendly home w/ private pool & boat docks

                                                    Florida Keys / Sugarloaf Key

                                                    Sugarloaf Key house

                                                    5 18 28 nights min

                                                    • 5 bedrooms
                                                    • sleeps 18
                                                    • 28 nights min
                                                    • Swimming pool
                                                    • Child Friendly
                                                    • Car not necessary

                                                    Price per night from

                                                    $229

                                                    Price per night from

                                                    $229

                                                    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

                                                      $144

                                                      Price per night from

                                                      $144

                                                      Distance approx 7.52 km from Cudjoe Key

                                                        12

                                                        Private beach estate. Gated, tropical peace and quiet. Dock.

                                                        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

                                                        $465

                                                        Price per night from

                                                        $465

                                                        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

                                                          $345

                                                          Price per night from

                                                          $345

                                                          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

                                                            $394

                                                            Price per night from

                                                            $394

                                                            Distance approx 18.99 km from Cudjoe Key

                                                            (2) Very Good 

                                                              19

                                                              DISCOUNTED! 45' Luxury Yacht & Other Boats

                                                              Florida Keys / Key West

                                                              Key West yacht

                                                              2 6 2 nights min

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

                                                              Price per night from

                                                              $230

                                                              Responds fast!
                                                              avg. 2 hours 13 minutes

                                                              Price per night from

                                                              $230

                                                              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

                                                                $746

                                                                Price per night from

                                                                $746

                                                                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

                                                                  $538

                                                                  Price per night from

                                                                  $538

                                                                  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

                                                                    $395

                                                                    Price per night from

                                                                    $395

                                                                    Distance approx 19.77 km from Cudjoe Key

                                                                      15

                                                                      LAST MINUTE OFFER! 44' Sailing Yacht & Other Boats

                                                                      Florida Keys / Stock Island

                                                                      Stock Island yacht

                                                                      4 10 2 nights min

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

                                                                      Price per night from

                                                                      $403

                                                                      Responds fast!
                                                                      avg. 2 hours 13 minutes

                                                                      Price per night from

                                                                      $403

                                                                      Distance approx 19.76 km from Cudjoe Key

                                                                      (33) Excellent 

                                                                        28

                                                                        LAST MINUTE DISCOUNT! 48' Sailing Yacht. Other Yachts & Boats Available!

                                                                        Florida Keys / Key West

                                                                        Key West houseboat

                                                                        4 10 2 nights min

                                                                        • 4 bedrooms
                                                                        • sleeps 10
                                                                        • 2 nights min
                                                                        • Swimming pool
                                                                        • Child Friendly
                                                                        • Car not necessary

                                                                        Price per night from

                                                                        $458

                                                                        Responds fast!
                                                                        avg. 2 hours 13 minutes

                                                                        Price per night from

                                                                        $458

                                                                        Distance approx 19.72 km from Cudjoe Key

                                                                          16

                                                                          SPECIAL OFFER! Like New! 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

                                                                          $344

                                                                          Responds fast!
                                                                          avg. 2 hours 13 minutes

                                                                          Price per night from

                                                                          $344

                                                                          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

                                                                            $284

                                                                            Price per night from

                                                                            $284

                                                                            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

                                                                              $316

                                                                              Responds fast!
                                                                              avg. 2 hours 13 minutes

                                                                              Price per night from

                                                                              $316