Vacation Rentals with Pool in Florida Keys

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Filtering by: Swimming pool

1,029 vacation 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

    $241

    Price per night from

    $241

    (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

        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

        $455

        Price per night from

        $455

          0

          Oceanfront condo w/beach access, shared tennis, pool, etc. - marina available!

          Key Largo / Tavernier

          Tavernier house

          2 6 min stay varies

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

          Price per night from

          $174

          Responds fast!
          avg. 2 hours 6 minutes

          Price per night from

          $174

          (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 42 minutes

            Price per night from

            $236

            (16) 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

              $213

              Responds fast!
              avg. 3 hours 54 minutes

              Price per night from

              $213

              (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

                $295

                Price per night from

                $295

                  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

                  (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

                    (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

                        36

                        Keys Cove Home #4 Wave from it all

                        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. 43 minutes

                        Price per night from

                        $490

                        (69) 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

                          $375

                          Price per night from

                          $375

                            24

                            Bayside 3BR/3BA w/ Heated Pool, Dock Access, Rooftop Terrace & Stunning View

                            Florida Keys / Marathon

                            Marathon villa

                            3 8 7 nights min

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

                            Price per night from

                            $270

                            Price per night from

                            $270

                            (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

                              $228

                              Responds fast!
                              avg. 1 hour 8 minutes

                              Price per night from

                              $228

                              (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 39 minutes

                                Price per night from

                                $258

                                (36) 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

                                  (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

                                    $336

                                    Responds fast!
                                    avg. 1 hour 34 minutes

                                    Price per night from

                                    $336

                                    (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

                                      $341

                                      Price per night from

                                      $341

                                      (13) Very Good 

                                        32

                                        75731 Overseas Highway

                                        Florida Keys / Islamorada

                                        Islamorada house

                                        4 10 7 nights min

                                        • 4 bedrooms
                                        • sleeps 10
                                        • 7 nights min
                                        • Swimming pool
                                        • Child Friendly
                                        “Vacation of a lifetime!” I can't say enough good things about this home. It was beautiful, clean, and peaceful. The only thing that might be considered a down side is that all of the bedrooms are located upstairs, but that was not a problem for us. B
                                        …see more

                                        Price per night from

                                        $1,145

                                        Price per night from

                                        $1,145

                                        (40) Excellent 

                                          38

                                          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

                                          $399

                                          Responds fast!
                                          avg. 1 hour 59 minutes

                                          Price per night from

                                          $399

                                          (1) Very Good 

                                            50

                                            Villa Sombrero, Marathon

                                            Florida Keys / Marathon

                                            Marathon house

                                            5 10 7 nights min

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

                                            Price per night from

                                            $458

                                            Responds fast!
                                            avg. 3 hours 9 minutes

                                            Price per night from

                                            $458

                                            (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

                                              (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. 28 minutes

                                                Price per night from

                                                $201

                                                (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

                                                  (4) Excellent 

                                                    48

                                                    Key West Condo close to the Ocean

                                                    Florida Keys / Key West

                                                    Key West condo

                                                    2 6 3 nights min

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

                                                    Price per night from

                                                    $342

                                                    Responds fast!
                                                    avg. 2 hours 11 minutes

                                                    Price per night from

                                                    $342

                                                      23

                                                      New 3 bedroom luxury condos just 10 mins from 10 beaches!!

                                                      Florida Keys / Dry Tortugas National Park

                                                      Dry Tortugas National Park apartment

                                                      3 5 min stay varies

                                                      • 3 bedrooms
                                                      • sleeps 5
                                                      • min stay varies
                                                      • Swimming pool
                                                      • Ask about children
                                                      • Air conditioning

                                                      Price per night from

                                                      $115

                                                      Price per night from

                                                      $115

                                                      (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

                                                        $1,492

                                                        Price per night from

                                                        $1,492

                                                          52

                                                          Colorful beachside condo w/ shared pool & hot tub - see the ocean from your deck

                                                          Key Largo / Tavernier

                                                          Tavernier house

                                                          1 2 28 nights min

                                                          • 1 bedroom
                                                          • sleeps 2
                                                          • 28 nights min
                                                          • Swimming pool
                                                          • Child Friendly
                                                          • Car not necessary

                                                          Price per night from

                                                          $108

                                                          Responds fast!
                                                          avg. 1 hour 8 minutes

                                                          Price per night from

                                                          $108

                                                            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

                                                            (3) Average 

                                                              11

                                                              Key Largo Kampground Vacation

                                                              Florida Keys / Key Largo

                                                              Key Largo house

                                                              1 3 3 nights min

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

                                                              Price per night from

                                                              $143

                                                              Responds fast!
                                                              avg. 2 hours 56 minutes

                                                              Price per night from

                                                              $143

                                                              (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

                                                                (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

                                                                  $307

                                                                  Responds fast!
                                                                  avg. 13 minutes

                                                                  Price per night from

                                                                  $307

                                                                    32

                                                                    Keys Cove Home #3 Bikini Bottom

                                                                    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. 43 minutes

                                                                    Price per night from

                                                                    $490

                                                                    (37) Very Good 

                                                                      38

                                                                      Key Largo 2/2 Tropical Daze Oceanfront Condo

                                                                      Florida Keys / Key Largo

                                                                      Key Largo apartment

                                                                      2 4 3 nights min

                                                                      • 2 bedrooms
                                                                      • sleeps 4
                                                                      • 3 nights min
                                                                      • Beach / lakeside relaxation
                                                                      • Nearest beach 0 mi
                                                                      • Swimming pool
                                                                      “Couldn't be better!!!” If you are looking to rest and relax, look no further.
                                                                      …see more

                                                                      Price per night from

                                                                      $228

                                                                      Responds fast!
                                                                      avg. 59 minutes

                                                                      Price per night from

                                                                      $228

                                                                      (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

                                                                        $338

                                                                        Price per night from

                                                                        $338

                                                                        (6) Excellent 

                                                                          23

                                                                          Ocean pointe island retreat

                                                                          Key Largo / Tavernier

                                                                          Tavernier condo

                                                                          2 5 min stay varies

                                                                          • 2 bedrooms
                                                                          • sleeps 5
                                                                          • min stay varies
                                                                          • Beach / lakeside relaxation
                                                                          • Swimming pool
                                                                          • Child Friendly

                                                                          Price per night from

                                                                          $222

                                                                          Responds fast!
                                                                          avg. 3 hours 18 minutes

                                                                          Price per night from

                                                                          $222

                                                                          (5) Excellent 

                                                                            23

                                                                            Indigo Reef, 32' dock, Marathon FL

                                                                            Florida Keys / Marathon

                                                                            Marathon villa

                                                                            3 6 7 nights min

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

                                                                            Price per night from

                                                                            $456

                                                                            Price per night from

                                                                            $456

                                                                            (19) Very Good 

                                                                              18

                                                                              Gorgeous Spa Villa, Marina in Florida Keys

                                                                              Florida Keys / Duck Key

                                                                              Duck Key villa

                                                                              2 6 min stay varies

                                                                              • 2 bedrooms
                                                                              • sleeps 6
                                                                              • min stay varies
                                                                              • Beach / lakeside relaxation
                                                                              • Swimming pool
                                                                              • Child Friendly
                                                                              “Loved it” Just got back from staying in this Villa. We were very happy with everything. The villa was clean & beautifully decorated & the location was perfect. I have stayed in Hawks Cays Villas twice before & this was the nicest. We will stay here
                                                                              …see more

                                                                              Price per night from

                                                                              $175

                                                                              Responds fast!
                                                                              avg. 2 hours 45 minutes

                                                                              Price per night from

                                                                              $175