Vacation Rentals & House Rentals in Florida Keys

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1,172 house rentals

(3) Excellent 

    26

    Keys Spectacular Gulf of Mexico Views

    Florida Keys / Marathon

    Marathon house

    3 8 7 nights min

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

    Price per night from

    $236

    Price per night from

    $236

      20

      Oceanfrontparadise: 209

      Florida Keys / Islamorada

      Islamorada apartment

      2 4 7 nights min

      • 2 bedrooms
      • sleeps 4
      • 7 nights min
      • Child Friendly
      • Car not necessary

      Price per night from

      $287

      Price per night from

      $287

      (3) Very Good 

        16

        Conch Haven Old Town 1/1 MONTHLY Rental

        Florida Keys / Key West

        Key West apartment

        1 4 30 nights min

        • 1 bedroom
        • sleeps 4
        • 30 nights min
        • Beach / lakeside relaxation
        • Child Friendly
        • Car not necessary

        Price per night from

        $93

        Responds fast!
        avg. 3 hours 11 minutes

        Price per night from

        $93

        (67) Very Good 

        Certificate of Excellence

          11

          Steps to Duval, Old Town Charm -Grand Bahama Suite

          Florida Keys / Key West

          Key West apartment

          3 8 min stay varies

          • 3 bedrooms
          • sleeps 8
          • min stay varies
          • Beach / lakeside relaxation
          • Swimming pool
          • Car not necessary
          “Can't wait to return” We loved staying at the Grand Bahama suite. It was spacious, clean and centrally located just a street from all the action. We loved the courtyard and pool. I was a little concerned about parking but it worked out fine for us.
          …see more

          Certificate of Excellence

          Price per night from

          $377

          Price per night from

          $377

          (15) Excellent 

            21

            Islamorada Luxury Waterfront Condo with Boat Slip

            Florida Keys / Islamorada

            Islamorada apartment

            2 6 7 nights min

            • 2 bedrooms
            • sleeps 6
            • 7 nights min
            • Beach / lakeside relaxation
            • Swimming pool
            • Child Friendly
            “Beautifully appointed, waterside condo!” This property is a beautiful, two bedroom condo, very well appointed, with everything we needed for a great stay! Islamorada is a great middle point to see the other parts of the Keys, and close to great restau
            …see more

            Price per night from

            $214

            Price per night from

            $214

            (1) Excellent 

              27

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

              Florida Keys / Marathon

              Marathon house

              2 6 7 nights min

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

              Price per night from

              $287

              Price per night from

              $287

              (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

                (52) Very Good 

                Certificate of Excellence

                  17

                  Best Location, 1/2 Block to Duval, Bimini Suite

                  Florida Keys / Key West

                  Key West apartment

                  2 5 min stay varies

                  • 2 bedrooms
                  • sleeps 5
                  • min stay varies
                  • Beach / lakeside relaxation
                  • Swimming pool
                  • Car not necessary
                  “Perfect!” This was the perfect size suite for 4 adults, with a little pool oasis right off our doorstep, in the center of it all without the noise of Duval. Loved every second of my stay!
                  …see more

                  Certificate of Excellence

                  Price per night from

                  $297

                  Price per night from

                  $297

                    19

                    Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach

                    Florida Keys / Key West

                    Key West townhouse

                    2 6 min stay varies

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

                    Price per night from

                    $457

                    Price per night from

                    $457

                    (5) Excellent 

                      36

                      Beautiful Condo - Moon Bay - Waterfront - Spectacular Views in Key Largo

                      Florida Keys / Key Largo

                      Key Largo apartment

                      2 6 6 nights min

                      • 2 bedrooms
                      • sleeps 6
                      • 6 nights min
                      • Child Friendly
                      “Excellent Condo” Oly was very accommodating and the place was beautiful and emaculate, the kitchen was fully stocked with everything you need. The beds were very comfortable and the ceiling fans were a nice addition. The facilities were also very clea
                      …see more

                      Price per night from

                      $229

                      Price per night from

                      $229

                      (34) Excellent 

                      Certificate of Excellence

                        14

                        Center of It All - Paradise Island Suite

                        Florida Keys / Key West

                        Key West apartment

                        2 6 min stay varies

                        • 2 bedrooms
                        • sleeps 6
                        • min stay varies
                        • Beach / lakeside relaxation
                        • Swimming pool
                        • Car not necessary
                        “Great location in the heart of Old Town Key West, just a block off Duval..” We stayed in the Paradise Suite. Great front porch to hang out on, pool in back with pergola for lounging. Place was set up perfect, pool towels hanging by the door, bathroom
                        …see more

                        Certificate of Excellence

                        Price per night from

                        $286

                        Price per night from

                        $286

                        (85) Very Good 

                          68

                          Private Home, with Beach Access, Best Value in the Keys

                          Florida Keys / Key Largo

                          Key Largo house

                          2 6 28 nights min

                          • 2 bedrooms
                          • sleeps 6
                          • 28 nights min
                          • Beach / lakeside relaxation
                          • Nearest beach 0.25 mi
                          • Child Friendly
                          “Perfect house for casual getaway” We wanted a clean and comfy place to stay for a long weekend that would be close to everything. This house had everything we wanted and more. We brought our 2 year old with us and felt like it was exactly the cozy a
                          …see more

                          Price per night from

                          $75

                          Price per night from

                          $75

                          (2) Excellent 

                            26

                            FL Keys Waterfront Pool Home 2 Bedrooms Sleeps 8 w/ 60 Feet of Dockage

                            Marathon / Marathon Shores

                            Marathon Shores house

                            2 8 min stay varies

                            • 2 bedrooms
                            • sleeps 8
                            • min stay varies
                            • Swimming pool
                            • Child Friendly
                            • Air conditioning

                            Price per night from

                            $258

                            Responds fast!
                            avg. 1 hour 53 minutes

                            Price per night from

                            $258

                              35

                              3BR Oasis in the Keys w/ Kayaks & Bikes - Sweeping Ocean Views in Every Room!

                              Florida Keys / Marathon

                              Marathon house

                              3 8 7 nights min

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

                              Price per night from

                              $303

                              Price per night from

                              $303

                              (63) Excellent 

                                26

                                Casa Del Sol, a Key West Vacation (Truman Annex)

                                Florida Keys / Key West

                                Key West house

                                2 6 7 nights min

                                • 2 bedrooms
                                • sleeps 6
                                • 7 nights min
                                • Beach / lakeside relaxation
                                • Swimming pool
                                • Child Friendly
                                “awesome” the condo was beautiful. very good location. 2 suggestions. the grill did not have gas . the bed that opens up to king. not so much, mattress is 2 different heights and slides if you try to sleep on it. very very uncomfortable.
                                …see more

                                Price per night from

                                $229

                                Responds fast!
                                avg. 1 hour 9 minutes

                                Price per night from

                                $229

                                (5) Very Good 

                                  26

                                  Large Townhouse in Mariner's Club Resort - 3 BR/3.5 Bath

                                  Key Largo / Tavernier

                                  Tavernier townhouse

                                  3 6 3 nights min

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

                                  Price per night from

                                  $338

                                  Responds fast!
                                  avg. 1 hour 24 minutes

                                  Price per night from

                                  $338

                                  (34) Excellent 

                                  Certificate of Excellence

                                    17

                                    1/2 Block to Duval, World of its own -Nassau Suite

                                    Florida Keys / Key West

                                    Key West apartment

                                    2 6 min stay varies

                                    • 2 bedrooms
                                    • sleeps 6
                                    • min stay varies
                                    • Swimming pool
                                    • Car not necessary
                                    • Air conditioning
                                    “Our wedding family stayed here awesome” Fabulous. Clean roomy pool fantastic. Short walk to schooners Wharf Both inside and outside area were excellent
                                    …see more

                                    Certificate of Excellence

                                    Price per night from

                                    $320

                                    Price per night from

                                    $320

                                    (2) Excellent 

                                      21

                                      Ocean-Front Caribbean Home.

                                      Florida Keys / Islamorada

                                      Islamorada house

                                      3 8 2 nights min

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

                                      Price per night from

                                      $1,500

                                      Price per night from

                                      $1,500

                                        36

                                        Keys Cove House 4

                                        Marathon / Marathon Shores

                                        Marathon Shores house

                                        4 10 min stay varies

                                        • 4 bedrooms
                                        • sleeps 10
                                        • min stay varies
                                        • Swimming pool
                                        • Child Friendly
                                        • Air conditioning

                                        Price per night from

                                        $490

                                        Responds fast!
                                        avg. 51 minutes

                                        Price per night from

                                        $490

                                        (5) Excellent 

                                          23

                                          76004 Overseas Highway

                                          Florida Keys / Islamorada

                                          Islamorada house

                                          4 8 7 nights min

                                          • 4 bedrooms
                                          • sleeps 8
                                          • 7 nights min
                                          • Child Friendly
                                          “Wonderful accommodations” Aside from being rainy for the majority of our stay, the accommodations were amazing. We will certainly be going back to this house. This house sleeps 8-10 adults comfortably. Freewheeler Realty was a pleasure to do busine
                                          …see more

                                          Price per night from

                                          $328

                                          Price per night from

                                          $328

                                          (7) Excellent 

                                            15

                                            Shelleys Rooftop Hideaway

                                            Florida Keys / Key West

                                            Key West apartment

                                            2 4 7 nights min

                                            • 2 bedrooms
                                            • sleeps 4
                                            • 7 nights min
                                            • Beach / lakeside relaxation
                                            • Swimming pool
                                            • Child Friendly
                                            “great place to stay” Close to every thing in Key West Walking distance to all of down town stores and bar my personal favorite
                                            …see more

                                            Price per night from

                                            $332

                                            Price per night from

                                            $332

                                            (3) Excellent 

                                              9

                                              Come relax in Islamorada, the tropical jewel of the Florida Keys!!

                                              Florida Keys / Islamorada

                                              Islamorada apartment

                                              1 4 7 nights min

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

                                              Price per night from

                                              $201

                                              Responds fast!
                                              avg. 23 minutes

                                              Price per night from

                                              $201

                                              (17) Excellent 

                                                37

                                                Amazing Ocean View Condo on the Beach!

                                                Florida Keys / Marathon

                                                Marathon apartment

                                                2 6 7 nights min

                                                • 2 bedrooms
                                                • sleeps 6
                                                • 7 nights min
                                                • Beach / lakeside relaxation
                                                • Swimming pool
                                                • Child Friendly
                                                “Our Spirits were renewed!” Things don't happen by chance! Little did we know six months ago when we booked our vacation how much we would really, really NEED a quiet and peaceful week! This little corner of Marathon is exactly that: quiet and peace
                                                …see more

                                                Price per night from

                                                $236

                                                Responds fast!
                                                avg. 2 hours 38 minutes

                                                Price per night from

                                                $236

                                                  24

                                                  1BR Restored Conch House w/ Pool & Deck

                                                  Florida Keys / Key West

                                                  Key West house

                                                  1 3 30 nights min

                                                  • 1 bedroom
                                                  • sleeps 3
                                                  • 30 nights min
                                                  • Swimming pool
                                                  • Child Friendly
                                                  • Air conditioning

                                                  Price per night from

                                                  $93

                                                  Price per night from

                                                  $93

                                                  (43) Very Good 

                                                    20

                                                    Waterfront Keys Home - Spectacular View, 37' Dock

                                                    Florida Keys / Marathon

                                                    Marathon house

                                                    2 6 7 nights min

                                                    • 2 bedrooms
                                                    • sleeps 6
                                                    • 7 nights min
                                                    • Beach / lakeside relaxation
                                                    • Nearest beach 2 mi
                                                    • Child Friendly
                                                    “Beautiful location” My husband, son, and I had a fantastic vacation here. The private boat dock and Bay Area was perfect for our needs. We were out in the gulf in a few minutes and could reach the Atlantic via Vaca Pass or 7 Mile bridge in just a sh
                                                    …see more

                                                    Price per night from

                                                    $143

                                                    Price per night from

                                                    $143

                                                      38

                                                      PARADISE OCEAN FRONT HOME

                                                      Florida Keys / Marathon

                                                      Marathon house

                                                      4 12 min stay varies

                                                      • 4 bedrooms
                                                      • sleeps 12
                                                      • min stay varies
                                                      • Nearest beach 5 mi
                                                      • Child Friendly
                                                      • Air conditioning

                                                      Price per night from

                                                      $287

                                                      Price per night from

                                                      $287

                                                      (13) Very Good 

                                                        32

                                                        75731 Overseas Highway

                                                        Florida Keys / Matecumbe Key

                                                        Matecumbe Key house

                                                        4 10 7 nights min

                                                        • 4 bedrooms
                                                        • sleeps 10
                                                        • 7 nights min
                                                        • Swimming pool
                                                        • Child Friendly
                                                        “Relaxing!” The Florida Keys are so much fun and so very casual. The house was a great way to get our family together for a week and we all enjoyed ourselves, I could have stayed for a month. The guys all went fishing and the rest of us floated in the
                                                        …see more

                                                        Price per night from

                                                        $1,064

                                                        Price per night from

                                                        $1,064

                                                        (3) Excellent 

                                                          44

                                                          ADVENTURE AWAITS I - MARINER'S CLUB 606 - KEY LARGO RESORT STYLE VACATION HOME

                                                          Florida Keys / Key Largo

                                                          Key Largo townhouse

                                                          4 11 min stay varies

                                                          • 4 bedrooms
                                                          • sleeps 11
                                                          • min stay varies
                                                          • Swimming pool
                                                          • Child Friendly
                                                          • Air conditioning

                                                          Price per night from

                                                          $343

                                                          Price per night from

                                                          $343

                                                          (13) Very Good 

                                                            27

                                                            BUCCANEER'S DEN - 20Ft. of Waterfront w/ Dock

                                                            Florida Keys / Key Largo

                                                            Key Largo house

                                                            2 2 3 nights min

                                                            • 2 bedrooms
                                                            • sleeps 2
                                                            • 3 nights min
                                                            • Beach / lakeside relaxation
                                                            • Nearest beach 19 mi
                                                            • Swimming pool
                                                            “All we expected and then some” The whole experience for us was great. From the quick response when we first asked about Rumrunners to our last day there. Nestor is great to work with, quick with any question we had, and had very good informational e
                                                            …see more

                                                            Price per night from

                                                            $93

                                                            Price per night from

                                                            $93

                                                            (5) Excellent 

                                                              19

                                                              75130 Overseas Highway

                                                              Florida Keys / Matecumbe Key

                                                              Matecumbe Key house

                                                              2 4 7 nights min

                                                              • 2 bedrooms
                                                              • sleeps 4
                                                              • 7 nights min
                                                              • Child Friendly
                                                              • Pet Friendly
                                                              “The view and location was excellent.” The house had most of the amenities I would expect at a beach location. You can't beat the sunsets over the bay! We snorkeled at Key Largo and took a day trip into key West, so the location was perfect. The area h
                                                              …see more

                                                              Price per night from

                                                              $190

                                                              Price per night from

                                                              $190

                                                              (4) Excellent 

                                                                31

                                                                Duck Key Paradise

                                                                Florida Keys / Duck Key

                                                                Duck Key house

                                                                3 9 28 nights min

                                                                • 3 bedrooms
                                                                • sleeps 9
                                                                • 28 nights min
                                                                • Nearest beach 19 mi
                                                                • Swimming pool
                                                                • Child Friendly

                                                                Price per night from

                                                                $308

                                                                Responds fast!
                                                                avg. 13 minutes

                                                                Price per night from

                                                                $308

                                                                  44

                                                                  Keys Cove House 2

                                                                  Marathon / Marathon Shores

                                                                  Marathon Shores house

                                                                  4 10 min stay varies

                                                                  • 4 bedrooms
                                                                  • sleeps 10
                                                                  • min stay varies
                                                                  • Child Friendly
                                                                  • Air conditioning

                                                                  Price per night from

                                                                  $490

                                                                  Responds fast!
                                                                  avg. 51 minutes

                                                                  Price per night from

                                                                  $490

                                                                  (1) Excellent 

                                                                    24

                                                                    Canal-Front 3BR w/ Private Pool, Boat Slip, Tiki Hut & Kayaks - Near Beach

                                                                    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

                                                                    $243

                                                                    Price per night from

                                                                    $243

                                                                    (85) Very Good 

                                                                      26

                                                                      Tropical Escape

                                                                      Florida Keys / Key West

                                                                      Key West apartment

                                                                      2 5 3 nights min

                                                                      • 2 bedrooms
                                                                      • sleeps 5
                                                                      • 3 nights min
                                                                      • Swimming pool
                                                                      • Child Friendly
                                                                      • Air conditioning
                                                                      “Very comfortable and all around great place to stay.” It was very clean, comfortable and homey. The pool was great and it's very close to Key West and a beach. We really enjoyed our stay. Provided plenty of towels, pool accessories, kitchenware, etc.
                                                                      …see more

                                                                      Price per night from

                                                                      $252

                                                                      Price per night from

                                                                      $252

                                                                      (3) Excellent 

                                                                      Certificate of Excellence

                                                                        19

                                                                        Escape to Paradise in a Gated Tropical Bayfront Estate (Free Wifi)

                                                                        Key Largo / Tavernier

                                                                        Tavernier house

                                                                        2 4 6 nights min

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

                                                                        Certificate of Excellence

                                                                        Price per night from

                                                                        $258

                                                                        Price per night from

                                                                        $258

                                                                        (13) Excellent 

                                                                          19

                                                                          Conch Key Villas Unit 1, Quiet, Clean with Awesome VIews in Paradise

                                                                          Florida Keys / Conch Key

                                                                          Conch Key apartment

                                                                          1 3 3 nights min

                                                                          • 1 bedroom
                                                                          • sleeps 3
                                                                          • 3 nights min
                                                                          • Beach / lakeside relaxation
                                                                          • Nearest beach 38 mi
                                                                          • Child Friendly

                                                                          Price per night from

                                                                          $189

                                                                          Responds fast!
                                                                          avg. 3 hours 48 minutes

                                                                          Price per night from

                                                                          $189

                                                                          (40) Excellent 

                                                                            22

                                                                            Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage

                                                                            Florida Keys / Key West

                                                                            Key West apartment

                                                                            2 6 min stay varies

                                                                            • 2 bedrooms
                                                                            • sleeps 6
                                                                            • min stay varies
                                                                            • Beach / lakeside relaxation
                                                                            • Nearest beach 0.2 mi
                                                                            • Swimming pool
                                                                            “Perfect place to experience Key West” This is a lovely condo with a tropical, quiet view. Many extras are included: beach towels, bikes, and kitchen supplies. The pool area was our favorite spot, and we had coffee every morning on the balcony with cha
                                                                            …see more

                                                                            Price per night from

                                                                            $401

                                                                            Responds fast!
                                                                            avg. 2 hours 5 minutes

                                                                            Price per night from

                                                                            $401

                                                                              98

                                                                              Jack's Flat

                                                                              Florida Keys / Key Colony Beach

                                                                              Key Colony Beach house

                                                                              2 8 2 nights min

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

                                                                              Price per night from

                                                                              $431

                                                                              Responds fast!
                                                                              avg. 3 hours 56 minutes

                                                                              Price per night from

                                                                              $431

                                                                              About Florida Keys

                                                                              Florida Keys, FL, including the islands of Key West, Key Largo, Islamorada, Marathon Key and Big Pine Key offers the perfect mix of family beach fun and peaceful vacation relaxation. Spend your days strolling one of the many boardwalks, or swim, snorkel, and kayak in the pristine Gulf. After a long day, retreat back to your vacation rental home at night, escape the crowds, and watch the sunset across the Gulf from your personal porch or deck. With your own private tennis court and pool, luxuries that many rentals offer, you can have a great time without even leaving your vacation home.

                                                                              Wake up to the sound of waves rolling in and the scent of the salty ocean air, then walk just minutes to the beach for great boardwalk shopping, dining, and entertainment. Truly escape the winter chill by heading to the southernmost point in the United States, Key West, Florida. Take U.S. Highway 1, known to locals as "The Overseas Highway" to get there, and enjoy the breath-taking natural beauty of the ocean scenery and wilderness that borders the road.

                                                                              Here are a few additional suggestions for your trip to the Florida Keys:

                                                                              • Visit the Key West Butterfly & Nature Conservatory: Key West is home to a magnificent array of butterflies from South America, Africa, and Southeast Asia. This Conservatory emphasizes the importance of wildlife preservation, offering group tours, unique films, and resident rainforest birds guaranteed to ignite your love for wildlife.
                                                                              • Swim with the dolphins: Key West is known for its dolphin friendly environment and facilities that offer guests the opportunity to swim and play with these amazing animals.
                                                                              • Explore The Harry S. Truman Little White House: Established in 1890 as a command center during the Spanish American War, this house was later used as a means of escape during the Cold War. For years, presidents relaxed and restored body and mind here while dealing with war threats. The site is now a living history museum.
                                                                              • Sleep under the stars: Spend a night under the legendary stars of Key West. Florida Keys campgrounds are plentiful, and Florida Keys camping can also happen at sea. Charter a boat and drift off with the night sky above and the ocean below.
                                                                              • Take a sunset dinner cruise: Gourmet dinner cruises to Florida Keys' destinations are widely available. Nothing is more romantic than raising a glass on a luxury sailboat as the sun sets over the Atlantic.
                                                                              • Take a charter fishing trip: An experienced outfitter can provide the boat and equipment you need to pursue deep water species like marlin and swordfish.

                                                                              Whether you're here for a Florida Keys honeymoon, a family reunion, or a vacation getaway with friends, you'll easily find a perfect vacation rental with all the amenities you need to relax in style. Stay in a charming beach condo close to the restaurants and nightlife or rent an elegant villa with a balcony and stunning views of the ocean. You may also want to make some time during your vacation to visit nearby destinations like Naples or Marco Island.