Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more
62 vacation rentals
    0

    NEW LISTING! Waterfront condo with rooftop patio, balcony, and dock!

    Florida Keys / Marathon

    Marathon house

    2 4 7 nights min

    • 2 bedrooms
    • sleeps 4
    • 7 nights min
    • Car not necessary
    • Air conditioning

    Price per night from

    $149

    Responds fast!
    avg. 1 hour 58 minutes

    Price per night from

    $149

    (4) Excellent 

      22

      Key West Florida Beachfront Condo

      Florida Keys / Key West

      Key West condo

      2 6 5 nights min

      • 2 bedrooms
      • sleeps 6
      • 5 nights min
      • Beach / lakeside relaxation
      • Swimming pool
      • Child Friendly
      “Better than the photos” Condo is perfectly located at the beach. Well designed for easy living both inside and out. Great advise on where to visit and eat thanks
      …see more

      Price per night from

      $371

      Price per night from

      $371

        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

        $205

        Price per night from

        $205

          47

          371 Pool for You Home

          Florida Keys / Key Colony Beach

          Key Colony Beach house

          3 8 7 nights min

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

          Price per night from

          $386

          Price per night from

          $386

            46

            P48~ Keys Cottage

            Marathon / Marathon Shores

            Marathon Shores house

            2 4 7 nights min

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

            Price per night from

            $171

            Price per night from

            $171

              19

              A Touch Of Havana In Key West

              Florida Keys / Key West

              Key West condo

              2 4 7 nights min

              • 2 bedrooms
              • sleeps 4
              • 7 nights min
              • Nearest beach 0.5 mi
              • Swimming pool
              • Child Friendly

              Price per night from

              $352

              Responds fast!
              avg. 3 hours 43 minutes

              Price per night from

              $352

              (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

                $1,793

                Responds fast!
                avg. 2 hours 42 minutes

                Price per night from

                $1,793

                (1) Excellent 

                  34

                  P21 3 bdm Mediterranean Getaway

                  Florida Keys / Key Colony Beach

                  Key Colony Beach house

                  3 8 7 nights min

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

                  Price per night from

                  $179

                  Price per night from

                  $179

                  (1) Very Good 

                    25

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

                    Florida Keys / Key Colony Beach

                    Key Colony Beach house

                    2 6 7 nights min

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

                    Price per night from

                    $213

                    Responds fast!
                    avg. 1 hour 19 minutes

                    Price per night from

                    $213

                      33

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

                      Marathon / Grassy Key

                      Grassy Key house

                      3 8 7 nights min

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

                      Price per night from

                      $524

                      Responds fast!
                      avg. 1 hour 51 minutes

                      Price per night from

                      $524

                      (2) Excellent 

                        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

                        $263

                        Price per night from

                        $263

                        (4) Excellent 

                          17

                          CORAL LAGOON RESORT NO. 3 WITH DOCK

                          Florida Keys / Marathon

                          Marathon villa

                          3 8 3 nights min

                          • 3 bedrooms
                          • sleeps 8
                          • 3 nights min
                          • Beach / lakeside relaxation
                          • Swimming pool
                          • Child Friendly
                          “Perfect getaway” My family and I stayed for the 1/2 marathon. The house was absolutely beautiful, clean and just the perfect place to relax. Loved waking up every morning to have coffee on the back decks overlooking the canal. My son loved seeing mana
                          …see more

                          Price per night from

                          $373

                          Responds fast!
                          avg. 3 hours 52 minutes

                          Price per night from

                          $373

                            30

                            P26 Dolphin Harbor

                            Florida Keys / Key Colony Beach

                            Key Colony Beach house

                            3 8 7 nights min

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

                            Price per night from

                            $271

                            Price per night from

                            $271

                              24

                              P17 Cozy Canal Front

                              Florida Keys / Key Colony Beach

                              Key Colony Beach house

                              3 6 7 nights min

                              • 3 bedrooms
                              • sleeps 6
                              • 7 nights min
                              • Nearest beach 0.1 mi
                              • Swimming pool
                              • Child Friendly

                              Price per night from

                              $184

                              Price per night from

                              $184

                              (1) Excellent 

                                104

                                P05 Villa Del Mare - 5 bdm Key Colony beach home

                                Florida Keys / Key Colony Beach

                                Key Colony Beach house

                                5 10 7 nights min

                                • 5 bedrooms
                                • sleeps 10
                                • 7 nights min
                                • Swimming pool
                                • Child Friendly
                                • Air conditioning

                                Price per night from

                                $734

                                Price per night from

                                $734

                                  31

                                  P67 Brand new construction 3 bdm duplex!

                                  Florida Keys / Key Colony Beach

                                  Key Colony Beach house

                                  3 8 7 nights min

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

                                  Price per night from

                                  $221

                                  Price per night from

                                  $221

                                  (2) Excellent 

                                    27

                                    Key Colony Beach Griffins' Getaway

                                    Florida Keys / Key Colony Beach

                                    Key Colony Beach house

                                    4 8 7 nights min

                                    • 4 bedrooms
                                    • sleeps 8
                                    • 7 nights min
                                    • Child Friendly

                                    Price per night from

                                    $328

                                    Price per night from

                                    $328

                                      22

                                      P34 Exquisite and spacious 4 bdm private pool home

                                      Florida Keys / Key Colony Beach

                                      Key Colony Beach house

                                      4 10 7 nights min

                                      • 4 bedrooms
                                      • sleeps 10
                                      • 7 nights min
                                      • Swimming pool
                                      • Child Friendly
                                      • Air conditioning

                                      Price per night from

                                      $292

                                      Price per night from

                                      $292

                                      (94) Excellent 

                                        92

                                        Sold, no longer avail. to rent! I can refer you to another rental on KCB!

                                        Florida Keys / Key Colony Beach

                                        Key Colony Beach house

                                        2 6 7 nights min

                                        • 2 bedrooms
                                        • sleeps 6
                                        • 7 nights min
                                        • Beach / lakeside relaxation
                                        • Nearest beach 0.2 mi
                                        • Child Friendly
                                        “Always a Great Place” Stayed at this home for our second time in three years and as always we were not disappointed. Experienced a few glitches upon arrival but the owner/manager (Patty) was only a phone call away and took care of everything expeditio
                                        …see more

                                        Price per night from

                                        $234

                                        Responds fast!
                                        avg. 2 hours 30 minutes

                                        Price per night from

                                        $234

                                          0

                                          Dog-friendly waterfront home w/35-ft dock, shared pool, hot tub, & Cabana Club!

                                          Florida Keys / Key Colony Beach

                                          Key Colony Beach house

                                          2 7 7 nights min

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

                                          Price per night from

                                          $200

                                          Responds fast!
                                          avg. 1 hour 42 minutes

                                          Price per night from

                                          $200

                                          (2) Excellent 

                                            25

                                            P50 - Beach Bums

                                            Florida Keys / Marathon

                                            Marathon house

                                            3 8 7 nights min

                                            • 3 bedrooms
                                            • sleeps 8
                                            • 7 nights min
                                            • Nearest beach 1 mi
                                            • Swimming pool
                                            • Child Friendly

                                            Price per night from

                                            $307

                                            Price per night from

                                            $307

                                            (2) Excellent 

                                              59

                                              P28 4 bedroom 3 bath pool home with dockage

                                              Florida Keys / Key Colony Beach

                                              Key Colony Beach house

                                              4 10 7 nights min

                                              • 4 bedrooms
                                              • sleeps 10
                                              • 7 nights min
                                              • Swimming pool
                                              • Child Friendly
                                              • Air conditioning

                                              Price per night from

                                              $388

                                              Price per night from

                                              $388

                                                0

                                                NEW LISTING! Boot Key Harbor waterfront studio with dock and amazing water views

                                                Florida Keys / Marathon

                                                Marathon house

                                                1 2 7 nights min

                                                • 1 bedroom
                                                • sleeps 2
                                                • 7 nights min
                                                • Car not necessary
                                                • Air conditioning

                                                Price per night from

                                                $134

                                                Responds fast!
                                                avg. 1 hour 44 minutes

                                                Price per night from

                                                $134

                                                (21) Excellent 

                                                  53

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

                                                  Florida Keys / Key Colony Beach

                                                  Key Colony Beach cottage

                                                  2 4 7 nights min

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

                                                  Price per night from

                                                  $200

                                                  Price per night from

                                                  $200

                                                  (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

                                                    $275

                                                    Responds fast!
                                                    avg. 2 hours 35 minutes

                                                    Price per night from

                                                    $275

                                                    (12) Excellent 

                                                      70

                                                      Grab a Summer 2019 week before they are gone! Dock, Bikes, Kayak, 2 beach clubs

                                                      Florida Keys / Key Colony Beach

                                                      Key Colony Beach house

                                                      2 6 7 nights min

                                                      • 2 bedrooms
                                                      • sleeps 6
                                                      • 7 nights min
                                                      • Beach / lakeside relaxation
                                                      • Nearest beach 2 mi
                                                      • Swimming pool
                                                      “Paradise Found” This is an adorable property. It is so "keysie"! The decor is just lovely with all the amenities you need. The kitchen is fully equipped, there was a new set of pots and pans, crockpot, blender and anything else I needed. The grill
                                                      …see more

                                                      Price per night from

                                                      $196

                                                      Responds fast!
                                                      avg. 55 minutes

                                                      Price per night from

                                                      $196

                                                        0

                                                        NEW LISTING! Three-condo waterfront villa w/ 4 boat slips, 2 kayaks & roof deck!

                                                        Florida Keys / Marathon

                                                        Marathon apartment

                                                        4 8 7 nights min

                                                        • 4 bedrooms
                                                        • sleeps 8
                                                        • 7 nights min
                                                        • Car not necessary
                                                        • Air conditioning

                                                        Price per night from

                                                        $421

                                                        Responds fast!
                                                        avg. 1 hour 58 minutes

                                                        Price per night from

                                                        $421

                                                        (1) Very Good 

                                                          24

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

                                                          Florida Keys / Key Colony Beach

                                                          Key Colony Beach house

                                                          3 7 7 nights min

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

                                                          Price per night from

                                                          $314

                                                          Responds fast!
                                                          avg. 1 hour 50 minutes

                                                          Price per night from

                                                          $314

                                                            34

                                                            House, 2 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 6)

                                                            Florida Keys / Key West

                                                            Key West house

                                                            2 6 min stay varies

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

                                                            Price per night from

                                                            $716

                                                            Price per night from

                                                            $716

                                                            (6) Excellent 

                                                              32

                                                              Key Colony Beach Tropical Pool Home-Booking for Spring/Summer & Winter Holidays

                                                              Florida Keys / Key Colony Beach

                                                              Key Colony Beach house

                                                              3 9 7 nights min

                                                              • 3 bedrooms
                                                              • sleeps 9
                                                              • 7 nights min
                                                              • Beach / lakeside relaxation
                                                              • Swimming pool
                                                              • Child Friendly
                                                              “You will love this Home” We have stayed in this beautiful home for the last 5 winters. It has everything needed to make your stay relaxing and enjoyable. The home has a large well stocked kitchen, large flatscreen TV, comfortable furniture and we
                                                              …see more

                                                              Price per night from

                                                              $376

                                                              Responds fast!
                                                              avg. 16 minutes

                                                              Price per night from

                                                              $376

                                                              (2) Very Good 

                                                                29

                                                                P23 Vacation Retreat

                                                                Florida Keys / Key Colony Beach

                                                                Key Colony Beach house

                                                                3 8 7 nights min

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

                                                                Price per night from

                                                                $264

                                                                Price per night from

                                                                $264

                                                                (3) Excellent 

                                                                  12

                                                                  The Ocean Never Felt So Close!

                                                                  Florida Keys / Key Colony Beach

                                                                  Key Colony Beach house

                                                                  2 6 7 nights min

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

                                                                  Price per night from

                                                                  $160

                                                                  Responds fast!
                                                                  avg. 1 hour 41 minutes

                                                                  Price per night from

                                                                  $160

                                                                    30

                                                                    P62 ~ Easy Breezy KCB

                                                                    Florida Keys / Marathon

                                                                    Marathon house

                                                                    3 6 7 nights min

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

                                                                    Price per night from

                                                                    $179

                                                                    Price per night from

                                                                    $179

                                                                    (1) Excellent 

                                                                      29

                                                                      P31 Cozy Cove 2 bd pool home w/ deep water dockage

                                                                      Florida Keys / Key Colony Beach

                                                                      Key Colony Beach house

                                                                      2 4 7 nights min

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

                                                                      Price per night from

                                                                      $156

                                                                      Price per night from

                                                                      $156

                                                                        26

                                                                        A LITTLE PIECE OF THE CARIBBEAN IN THE U. S.

                                                                        Florida Keys / Key West

                                                                        Key West condo

                                                                        1 3 28 nights min

                                                                        • 1 bedroom
                                                                        • sleeps 3
                                                                        • 28 nights min
                                                                        • Car not necessary

                                                                        Price per night from

                                                                        $303

                                                                        Price per night from

                                                                        $303

                                                                          18

                                                                          Cameron's Luxury Waterfront Estate with Dockage

                                                                          Florida Keys / Key West

                                                                          Key West house

                                                                          3 6 30 nights min

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

                                                                          Price per night from

                                                                          $516

                                                                          Price per night from

                                                                          $516

                                                                            24

                                                                            Sunrise Retreat 3 bed 3 bath Pool Home

                                                                            Florida Keys / Key Colony Beach

                                                                            Key Colony Beach house

                                                                            3 8 7 nights min

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

                                                                            Price per night from

                                                                            $493

                                                                            Price per night from

                                                                            $493

                                                                              16

                                                                              Single Family Home, 3 Bedroom, 2 Bath, Pool and Electric Car, Great Value!

                                                                              Florida Keys / Key West

                                                                              Key West house

                                                                              3 6 28 nights min

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

                                                                              Price per night from

                                                                              $147

                                                                              Price per night from

                                                                              $147