Vacation Rentals with Pool in Islamorada

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Filtering by: Swimming pool

278 vacation rentals

(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

    $215

    Responds fast!
    avg. 3 hours 54 minutes

    Price per night from

    $215

    (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

      $1,506

      Price per night from

      $1,506

      (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

        (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

          (4) Excellent 

            21

            BEACON REEF 310

            Florida Keys / Islamorada

            Islamorada apartment

            2 4 min stay varies

            • 2 bedrooms
            • sleeps 4
            • min stay varies
            • Swimming pool
            • Ask about children

            Price per night from

            $110

            Price per night from

            $110

              22

              Dream Escape in Islamorada at Anglers Reef

              Florida Keys / Islamorada

              Islamorada villa

              2 6 7 nights min

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

              Price per night from

              $287

              Responds fast!
              avg. 2 hours 11 minutes

              Price per night from

              $287

              (2) Excellent 

                25

                MATECUMBE JEWEL

                Florida Keys / Islamorada

                Islamorada house

                3 6 min stay varies

                • 3 bedrooms
                • sleeps 6
                • min stay varies
                • Swimming pool
                • Ask about children
                • Pet Friendly
                “Our Lobster Trip to the Keys” My family and I stayed at the Matecumbe Jewel in the month of august for Lobster season. The home shows even better than the photos, was clean, well furnished and kept. We could not have asked for better accomodations wh
                …see more

                Price per night from

                $157

                Price per night from

                $157

                  65

                  100 Palo De Oro Drive

                  Florida Keys / Islamorada

                  Islamorada house

                  4 8 28 nights min

                  • 4 bedrooms
                  • sleeps 8
                  • 28 nights min
                  • Swimming pool
                  • Child Friendly

                  Price per night from

                  $430

                  Price per night from

                  $430

                  (5) Excellent 

                    31

                    FLORIDA KEYS OASIS # The Corona commercial-welcome ****7 DAY MINIMUM RENTAL****

                    Florida Keys / Islamorada

                    Islamorada house

                    5 12 4 nights min

                    • 5 bedrooms
                    • sleeps 12
                    • 4 nights min
                    • Nearest beach 4 mi
                    • Swimming pool
                    • Child Friendly
                    “Relax in Luxury” Great Location. Lots of nearby restaurants. Owners were extremely helpful in recommending attractions. A stunningly beautiful home with plenty of room for my large family to spread out. Pool was great. Swimming in warm shallow wa
                    …see more

                    Price per night from

                    $1,437

                    Responds fast!
                    avg. 2 hours 45 minutes

                    Price per night from

                    $1,437

                      25

                      Anglers Reef Islamorada Florida Sleeps 6

                      Florida Keys / Islamorada

                      Islamorada house

                      2 6 7 nights min

                      • 2 bedrooms
                      • sleeps 6
                      • 7 nights min
                      • Beach / lakeside relaxation
                      • Nearest beach 0 mi
                      • Swimming pool

                      Price per night from

                      $344

                      Price per night from

                      $344

                      (2) Excellent 

                        17

                        Incredible Luxury Home with Waterfront!! Paradise

                        Florida Keys / Islamorada

                        Islamorada house

                        5 12 7 nights min

                        • 5 bedrooms
                        • sleeps 12
                        • 7 nights min
                        • Swimming pool
                        • Child Friendly
                        • Air conditioning

                        Price per night from

                        $1,390

                        Price per night from

                        $1,390

                          40

                          SPACIOUS 2 BEDROOM TROPICAL OASIS WITH FLORIDA BAY SUNSET VIEWS!

                          Florida Keys / Islamorada

                          Islamorada condo

                          2 6 7 nights min

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

                          Price per night from

                          $196

                          Price per night from

                          $196

                            26

                            Dog-friendly, waterfront home w/ a private pool, hot tub & private beach

                            Florida Keys / Islamorada

                            Islamorada house

                            4 14 7 nights min

                            • 4 bedrooms
                            • sleeps 14
                            • 7 nights min
                            • Swimming pool
                            • Child Friendly
                            • Car not necessary

                            Price per night from

                            $1,166

                            Price per night from

                            $1,166

                            (7) Excellent 

                              18

                              No dockage allowed. Florida Keys. Beautiful condo. Short walk to the beach area.

                              Florida Keys / Islamorada

                              Islamorada villa

                              2 6 4 nights min

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

                              Price per night from

                              $286

                              Responds fast!
                              avg. 1 hour 36 minutes

                              Price per night from

                              $286

                              (28) Excellent 

                                38

                                Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental

                                Florida Keys / Islamorada

                                Islamorada house

                                3 8 7 nights min

                                • 3 bedrooms
                                • sleeps 8
                                • 7 nights min
                                • Beach / lakeside relaxation
                                • Swimming pool
                                • Child Friendly
                                “Comfortable home for family get-together” Positive experience overall: Our family of six adults had a tropical-feeling destination Christmas here. The house easily accommodated all of us, and we enjoyed the wrap-around porch and pool. We appreciated
                                …see more

                                Price per night from

                                $608

                                Responds fast!
                                avg. 1 hour 51 minutes

                                Price per night from

                                $608

                                (3) Excellent 

                                  40

                                  All NEW Interior Oceanfront 5th Floor End Unit, Pool, WiFi, Great Ocean Views!

                                  Florida Keys / Islamorada

                                  Islamorada condo

                                  2 4 7 nights min

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

                                  Price per night from

                                  $173

                                  Responds fast!
                                  avg. 3 hours 22 minutes

                                  Price per night from

                                  $173

                                  (2) Excellent 

                                    25

                                    PALMS 309

                                    Florida Keys / Islamorada

                                    Islamorada house

                                    2 5 min stay varies

                                    • 2 bedrooms
                                    • sleeps 5
                                    • min stay varies
                                    • Swimming pool
                                    • Ask about children

                                    Price per night from

                                    $85

                                    Price per night from

                                    $85

                                    (1) Excellent 

                                      24

                                      LYONS LANDING

                                      Florida Keys / Islamorada

                                      Islamorada house

                                      4 10 min stay varies

                                      • 4 bedrooms
                                      • sleeps 10
                                      • min stay varies
                                      • Swimming pool
                                      • Ask about children
                                      • Pet Friendly

                                      Price per night from

                                      $245

                                      Price per night from

                                      $245

                                      (2) Excellent 

                                        24

                                        PALMS 314

                                        Florida Keys / Islamorada

                                        Islamorada apartment

                                        2 5 min stay varies

                                        • 2 bedrooms
                                        • sleeps 5
                                        • min stay varies
                                        • Swimming pool
                                        • Ask about children
                                        “Wow, what a beautiful view” This condo was clean, nicely furnished and had a view to die for. We really appreciated the washer and dryer in the unit, which most did not have. Also, being on the end we had "the window" in the master bedroom and in the
                                        …see more

                                        Price per night from

                                        $80

                                        Price per night from

                                        $80

                                        (5) Excellent 

                                          19

                                          THIS IS IT! Magnificent Oceanfront Paradise! WE ARE OPEN!!

                                          Florida Keys / Islamorada

                                          Islamorada condo

                                          2 5 7 nights min

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

                                          Price per night from

                                          $164

                                          Responds fast!
                                          avg. 3 hours 4 minutes

                                          Price per night from

                                          $164

                                            33

                                            152 Valencia Drive

                                            Florida Keys / Islamorada

                                            Islamorada house

                                            4 8 28 nights min

                                            • 4 bedrooms
                                            • sleeps 8
                                            • 28 nights min
                                            • Swimming pool
                                            • Child Friendly
                                            • Pet Friendly

                                            Price per night from

                                            $268

                                            Price per night from

                                            $268

                                              51

                                              Islamorada Paradise

                                              Florida Keys / Islamorada

                                              Islamorada house

                                              3 6 30 nights min

                                              • 3 bedrooms
                                              • sleeps 6
                                              • 30 nights min
                                              • Swimming pool
                                              • Air conditioning
                                              • Private garden

                                              Price per night from

                                              $687

                                              Price per night from

                                              $687

                                              (17) Very Good 

                                                35

                                                FALL SPECIAL DISCOUNTED PRICING!!!

                                                Florida Keys / Islamorada

                                                Islamorada condo

                                                3 6 7 nights min

                                                • 3 bedrooms
                                                • sleeps 6
                                                • 7 nights min
                                                • Beach / lakeside relaxation
                                                • Swimming pool
                                                • Child Friendly
                                                “The Best Keys Location” My family stayed at this lovely Futura Yacht Club Condo for three weeks this July. We have stayed at many other units in this complex over the years but this unit was one of the nicest we have seen. The unit has been remodel
                                                …see more

                                                Price per night from

                                                $197

                                                Responds fast!
                                                avg. 3 hours 12 minutes

                                                Price per night from

                                                $197

                                                (1) Excellent 

                                                  24

                                                  PALMS 214

                                                  Florida Keys / Islamorada

                                                  Islamorada apartment

                                                  2 4 min stay varies

                                                  • 2 bedrooms
                                                  • sleeps 4
                                                  • min stay varies
                                                  • Swimming pool
                                                  • Ask about children

                                                  Price per night from

                                                  $76

                                                  Price per night from

                                                  $76

                                                  (15) Excellent 

                                                    25

                                                    BROCK HAUS ON THE GULF

                                                    Florida Keys / Islamorada

                                                    Islamorada apartment

                                                    2 6 7 nights min

                                                    • 2 bedrooms
                                                    • sleeps 6
                                                    • 7 nights min
                                                    • Swimming pool
                                                    • Ask about children
                                                    “Absolutely Beautiful and convenient for boaters!” Our family stayed here for a week in late March. We had plenty of room and everything we needed was available. This is a gorgeous condo overlooking the Florida Bay. You get to see an awesome sunset eve
                                                    …see more

                                                    Price per night from

                                                    $225

                                                    Price per night from

                                                    $225

                                                    (4) Very Good 

                                                      6

                                                      Islamorada 2-bedroom Condo

                                                      Florida Keys / Islamorada

                                                      Islamorada apartment

                                                      2 6 7 nights min

                                                      • 2 bedrooms
                                                      • sleeps 6
                                                      • 7 nights min
                                                      • Beach / lakeside relaxation
                                                      • Swimming pool
                                                      • Child Friendly
                                                      “Fantastic Views” This 6th floor unit has all you need for a relaxing vacation. Close proximity to local attractions and fantastic Seafood Restaurants. The Hospital is one mile from the condo and has an excellent rehab and emergency. The complex h
                                                      …see more

                                                      Price per night from

                                                      $185

                                                      Price per night from

                                                      $185

                                                      (8) Very Good 

                                                      Certificate of Excellence

                                                        14

                                                        Oceanfront 2 Bedroom/2 Bathroom Well Maintained Condo with Large Balcony

                                                        Florida Keys / Islamorada

                                                        Islamorada condo

                                                        2 5 min stay varies

                                                        • 2 bedrooms
                                                        • sleeps 5
                                                        • min stay varies
                                                        • Swimming pool
                                                        • Child Friendly
                                                        • Air conditioning
                                                        “Amazing view! Absolutely gorgeous!” My two teenage daughters and I stayed at this condo and it worked out perfect for us! The view is stunning, and I loved to just sit in the living room and look out at the ocean. The condo was very clean, and reall
                                                        …see more

                                                        Certificate of Excellence

                                                        Price per night from

                                                        $173

                                                        Responds fast!
                                                        avg. 3 hours 51 minutes

                                                        Price per night from

                                                        $173

                                                          22

                                                          FLAMINGO COTTAGE

                                                          Florida Keys / Islamorada

                                                          Islamorada house

                                                          2 6 min stay varies

                                                          • 2 bedrooms
                                                          • sleeps 6
                                                          • min stay varies
                                                          • Swimming pool
                                                          • Ask about children
                                                          • Pet Friendly

                                                          Price per night from

                                                          $100

                                                          Price per night from

                                                          $100

                                                          (3) Very Good 

                                                            29

                                                            Modern Executive Bay Club Condo with Pool & Beach

                                                            Florida Keys / Islamorada

                                                            Islamorada apartment

                                                            3 8 28 nights min

                                                            • 3 bedrooms
                                                            • sleeps 8
                                                            • 28 nights min
                                                            • Swimming pool
                                                            • Child Friendly
                                                            • Air conditioning
                                                            “Great condo, perfect location!” I have two small children and the condo was perfect and comfortable for the entire family. It was nicely remodeled. The pool and dock area were very nice. Security was visible and very friendly. The location was close t
                                                            …see more

                                                            Price per night from

                                                            $161

                                                            Responds fast!
                                                            avg. 57 minutes

                                                            Price per night from

                                                            $161

                                                            (1) Excellent 

                                                              25

                                                              LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

                                                              Florida Keys / Islamorada

                                                              Islamorada villa

                                                              2 6 7 nights min

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

                                                              Price per night from

                                                              $320

                                                              Price per night from

                                                              $320

                                                                25

                                                                6th-floor oceanfront condo w/sweeping ocean views & shared pool

                                                                Florida Keys / Islamorada

                                                                Islamorada house

                                                                2 4 7 nights min

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

                                                                Price per night from

                                                                $128

                                                                Price per night from

                                                                $128

                                                                  25

                                                                  PALMS 402

                                                                  Florida Keys / Islamorada

                                                                  Islamorada apartment

                                                                  2 4 min stay varies

                                                                  • 2 bedrooms
                                                                  • sleeps 4
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Ask about children

                                                                  Price per night from

                                                                  $80

                                                                  Price per night from

                                                                  $80

                                                                    25

                                                                    THE PALMS 405 - 93

                                                                    Florida Keys / Islamorada

                                                                    Islamorada apartment

                                                                    2 6 min stay varies

                                                                    • 2 bedrooms
                                                                    • sleeps 6
                                                                    • min stay varies
                                                                    • Swimming pool
                                                                    • Ask about children

                                                                    Price per night from

                                                                    $103

                                                                    Price per night from

                                                                    $103

                                                                      26

                                                                      Experience the Florida Keys like never before!!!

                                                                      Florida Keys / Islamorada

                                                                      Islamorada condo

                                                                      2 6 30 nights min

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

                                                                      Price per night from

                                                                      $246

                                                                      Price per night from

                                                                      $246

                                                                      (2) Excellent 

                                                                        43

                                                                        100' Private Beach Front Ocean Front Estate

                                                                        Florida Keys / Islamorada

                                                                        Islamorada house

                                                                        4 12 min stay varies

                                                                        • 4 bedrooms
                                                                        • sleeps 12
                                                                        • min stay varies
                                                                        • Nearest beach 0 mi
                                                                        • Swimming pool
                                                                        • Child Friendly

                                                                        Price per night from

                                                                        $953

                                                                        Responds fast!
                                                                        avg. 2 hours 17 minutes

                                                                        Price per night from

                                                                        $953

                                                                        (6) Excellent 

                                                                          20

                                                                          Luxury condo overlooking harbor with ocean view

                                                                          Florida Keys / Islamorada

                                                                          Islamorada condo

                                                                          3 6 7 nights min

                                                                          • 3 bedrooms
                                                                          • sleeps 6
                                                                          • 7 nights min
                                                                          • Nearest beach 2 mi
                                                                          • Swimming pool
                                                                          • Child Friendly

                                                                          Price per night from

                                                                          $310

                                                                          Responds fast!
                                                                          avg. 1 hour 7 minutes

                                                                          Price per night from

                                                                          $310

                                                                          (4) Excellent 

                                                                            19

                                                                            Bay Front Beauty/ Summer Sea Must See!!!!

                                                                            Florida Keys / Islamorada

                                                                            Islamorada condo

                                                                            1 4 28 nights min

                                                                            • 1 bedroom
                                                                            • sleeps 4
                                                                            • 28 nights min
                                                                            • Nearest beach 0 mi
                                                                            • Swimming pool
                                                                            • Child Friendly

                                                                            Price per night from

                                                                            $159

                                                                            Responds fast!
                                                                            avg. 17 minutes

                                                                            Price per night from

                                                                            $159

                                                                              48

                                                                              50 Schooner Bay

                                                                              Florida Keys / Islamorada

                                                                              Islamorada house

                                                                              4 8 7 nights min

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

                                                                              Price per night from

                                                                              $735

                                                                              Price per night from

                                                                              $735