Vacation Rentals with Hot Tub in Islamorada

Close

Enter dates for more accurate prices

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

Filtering by: Jacuzzi or hot tub

150 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

    $213

    Responds fast!
    avg. 3 hours 54 minutes

    Price per night from

    $213

    (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

      $1,139

      Price per night from

      $1,139

      (6) Very Good 

        14

        THE PERFECT GETAWAY

        Florida Keys / Islamorada

        Islamorada house

        4 10 7 nights min

        • 4 bedrooms
        • sleeps 10
        • 7 nights min
        • Beach / lakeside relaxation
        • Child Friendly
        • Air conditioning
        “The owner was understanding and worked with us” I was scheduled to rent from Dec 29th to Jan 4th and expected 7 friends to join me. For multiple personal reasons four of the seven had to back out and it is not the place you want to be without the full
        …see more

        Price per night from

        $407

        Price per night from

        $407

        (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

          $1,415

          Price per night from

          $1,415

          (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

              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

              $427

              Price per night from

              $427

                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

                $1,167

                Responds fast!
                avg. 37 minutes

                Price per night from

                $1,167

                  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

                  (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

                    (4) Excellent 

                      29

                      82754 Overseas Highway

                      Florida Keys / Islamorada

                      Islamorada house

                      5 10 7 nights min

                      • 5 bedrooms
                      • sleeps 10
                      • 7 nights min
                      • Child Friendly

                      Price per night from

                      $892

                      Price per night from

                      $892

                      (5) Excellent 

                        21

                        SANCTUARY IN PARADISE

                        Florida Keys / Islamorada

                        Islamorada house

                        4 10 7 nights min

                        • 4 bedrooms
                        • sleeps 10
                        • 7 nights min
                        • Beach / lakeside relaxation
                        • Child Friendly
                        • Air conditioning
                        “What Florida dreams are made of” Growing up in South Florida and the Keys but now moved farm away, I wanted to show my husband and young children the Florida I remembered as a child. This my friends was more than my dreams could have asked for! We wer
                        …see more

                        Price per night from

                        $498

                        Price per night from

                        $498

                        (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

                          (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

                            (1) Excellent 

                              46

                              Paradise Beach Sandy Oceanfront

                              Florida Keys / Islamorada

                              Islamorada house

                              4 10 7 nights min

                              • 4 bedrooms
                              • sleeps 10
                              • 7 nights min
                              • Child Friendly
                              • Pet Friendly

                              Price per night from

                              $687

                              Responds fast!
                              avg. 1 hour 58 minutes

                              Price per night from

                              $687

                              (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

                                $307

                                Responds fast!
                                avg. 1 hour 7 minutes

                                Price per night from

                                $307

                                  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

                                    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

                                    (2) Excellent 

                                      25

                                      BEACON REEF 222

                                      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

                                      $146

                                      Price per night from

                                      $146

                                      (5) Excellent 

                                        20

                                        Luxury 3 BR condo, boatslip, easy accces to ocean

                                        Florida Keys / Islamorada

                                        Islamorada condo

                                        3 8 7 nights min

                                        • 3 bedrooms
                                        • sleeps 8
                                        • 7 nights min
                                        • Beach / lakeside relaxation
                                        • Swimming pool
                                        • Child Friendly

                                        Price per night from

                                        $284

                                        Responds fast!
                                        avg. 3 hours 18 minutes

                                        Price per night from

                                        $284

                                        (1) Excellent 

                                          25

                                          BEACON REEF 501

                                          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

                                          (1) Excellent 

                                            24

                                            PALMS 417

                                            Florida Keys / Islamorada

                                            Islamorada apartment

                                            1 4 min stay varies

                                            • 1 bedroom
                                            • sleeps 4
                                            • min stay varies
                                            • Swimming pool
                                            • Ask about children
                                            “Paradise on the ocean” We rented Palm 417 for the month of March 2014. The condo has been very nicely updated and although not direct ocean front view; it does have partial view of the ocean side and a good view of the bay side with amazing sunsets. P
                                            …see more

                                            Price per night from

                                            $70

                                            Price per night from

                                            $70

                                              20

                                              San Roc - Private 150 Ft Oceanfront 2.5 Acre Millionaire Row Estate, Pool, Spa,

                                              Florida Keys / Islamorada

                                              Islamorada house

                                              4 8 7 nights min

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

                                              Price per night from

                                              $786

                                              Responds fast!
                                              avg. 1 hour 58 minutes

                                              Price per night from

                                              $786

                                                14

                                                BEAUTIFUL BAY HARBOUR CONDO W/ BOAT DOCK! OFFSEASON RATES FOR OCT AND NOV!

                                                Florida Keys / Islamorada

                                                Islamorada condo

                                                3 8 7 nights min

                                                • 3 bedrooms
                                                • sleeps 8
                                                • 7 nights min
                                                • Beach / lakeside relaxation
                                                • Nearest beach 0 mi
                                                • Swimming pool

                                                Price per night from

                                                $407

                                                Price per night from

                                                $407

                                                  21

                                                  Elegant Bay Harbour Condo with 50 Foot Boat Slip

                                                  Florida Keys / Islamorada

                                                  Islamorada apartment

                                                  3 6 7 nights min

                                                  • 3 bedrooms
                                                  • sleeps 6
                                                  • 7 nights min
                                                  • Beach / lakeside relaxation
                                                  • Nearest beach 0.8 mi
                                                  • Swimming pool

                                                  Price per night from

                                                  $489

                                                  Price per night from

                                                  $489

                                                  (1) Excellent 

                                                    15

                                                    Fabulous 6 Bedrooms /4 Bathrooms Tropical Waterfront Pool Home!

                                                    Florida Keys / Islamorada

                                                    Islamorada house

                                                    3 12 28 nights min

                                                    • 3 bedrooms
                                                    • sleeps 12
                                                    • 28 nights min
                                                    • Nearest beach 1 mi
                                                    • Swimming pool
                                                    • Child Friendly

                                                    Price per night from

                                                    $268

                                                    Responds fast!
                                                    avg. 1 hour 44 minutes

                                                    Price per night from

                                                    $268

                                                      19

                                                      Paradise Found - Sandy Beach, Beachside Bar, Great Views, And Dock

                                                      Florida Keys / Islamorada

                                                      Islamorada villa

                                                      3 6 30 nights min

                                                      • 3 bedrooms
                                                      • sleeps 6
                                                      • 30 nights min
                                                      • Child Friendly
                                                      • Air conditioning
                                                      • Private garden

                                                      Price per night from

                                                      $401

                                                      Price per night from

                                                      $401

                                                        25

                                                        PALMS 407

                                                        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

                                                        (1) Very Good 

                                                          24

                                                          PALMS 301

                                                          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

                                                          $76

                                                          Price per night from

                                                          $76

                                                            29

                                                            AZALEA WARTERFRONT

                                                            Florida Keys / Islamorada

                                                            Islamorada house

                                                            3 6 60 nights min

                                                            • 3 bedrooms
                                                            • sleeps 6
                                                            • 60 nights min
                                                            • Suitable for children age 5+
                                                            • Air conditioning
                                                            • Private garden

                                                            Price per night from

                                                            $171

                                                            Price per night from

                                                            $171

                                                              21

                                                              PALMS 404

                                                              Florida Keys / Islamorada

                                                              Islamorada condo

                                                              2 6 30 nights min

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

                                                              Price per night from

                                                              $77

                                                              Price per night from

                                                              $77

                                                              (1) Excellent 

                                                                15

                                                                Islamorada cottage on deep water canal

                                                                Florida Keys / Islamorada

                                                                Islamorada house

                                                                2 6 30 nights min

                                                                • 2 bedrooms
                                                                • sleeps 6
                                                                • 30 nights min
                                                                • Child Friendly
                                                                • Air conditioning
                                                                • Private garden

                                                                Price per night from

                                                                $171

                                                                Price per night from

                                                                $171

                                                                  24

                                                                  Oceanfront Islamorada Condo with Huge T-Dock

                                                                  Florida Keys / Islamorada

                                                                  Islamorada condo

                                                                  2 4 30 nights min

                                                                  • 2 bedrooms
                                                                  • sleeps 4
                                                                  • 30 nights min
                                                                  • Child Friendly
                                                                  • Air conditioning

                                                                  Price per night from

                                                                  $151

                                                                  Price per night from

                                                                  $151

                                                                    4

                                                                    Oceanfront 2/2 Condo in Beacon Reef - Free boat dock

                                                                    Florida Keys / Islamorada

                                                                    Islamorada condo

                                                                    2 4 28 nights min

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

                                                                    Price per night from

                                                                    $287

                                                                    Price per night from

                                                                    $287

                                                                      25

                                                                      Luxurious Ocean View Condo w/Heated Pool & Jacuzzi

                                                                      Florida Keys / Islamorada

                                                                      Islamorada apartment

                                                                      2 4 min stay varies

                                                                      • 2 bedrooms
                                                                      • sleeps 4
                                                                      • min stay varies
                                                                      • Swimming pool
                                                                      • Child Friendly
                                                                      • Pet Friendly

                                                                      Price per night from

                                                                      $230

                                                                      Responds fast!
                                                                      avg. 58 minutes

                                                                      Price per night from

                                                                      $230

                                                                      (8) Excellent 

                                                                        22

                                                                        The PERFECT Escape with pool & jacuzzi

                                                                        Florida Keys / Islamorada

                                                                        Islamorada house

                                                                        4 8 7 nights min

                                                                        • 4 bedrooms
                                                                        • sleeps 8
                                                                        • 7 nights min
                                                                        • Beach / lakeside relaxation
                                                                        • Nearest beach 3 mi
                                                                        • Swimming pool

                                                                        Price per night from

                                                                        $427

                                                                        Price per night from

                                                                        $427

                                                                        (4) Very Good 

                                                                          41

                                                                          3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.

                                                                          Florida Keys / Islamorada

                                                                          Islamorada apartment

                                                                          3 6 28 nights min

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

                                                                          Price per night from

                                                                          $269

                                                                          Price per night from

                                                                          $269

                                                                          Great rentals within 20 miles that match your search

                                                                          Distance approx 5.76 km from Islamorada Show on Map

                                                                          (7) Very Good 

                                                                            36

                                                                            Licensed Manager W/10 Rentals Available - 2/2 Suite - OCEANFRONT BEACH RESORT!

                                                                            Florida Keys / Key Largo

                                                                            Key Largo apartment

                                                                            2 6 min stay varies

                                                                            • 2 bedrooms
                                                                            • sleeps 6
                                                                            • min stay varies
                                                                            • Beach / lakeside relaxation
                                                                            • Swimming pool
                                                                            • Child Friendly
                                                                            “A great location for accomplishing our interests while visiting” This rental was a perfect set up for two people - also very clean, convenient and seeing the egret's nest outside the patio was special. The beach chairs in the closet need attention as
                                                                            …see more

                                                                            Price per night from

                                                                            $153

                                                                            Price per night from

                                                                            $153

                                                                            Distance approx 13.34 km from Islamorada

                                                                            (8) Very Good 

                                                                              15

                                                                              Escape to Paradise

                                                                              Florida Keys / Key Largo

                                                                              Key Largo house

                                                                              4 8 30 nights min

                                                                              • 4 bedrooms
                                                                              • sleeps 8
                                                                              • 30 nights min
                                                                              • Beach / lakeside relaxation
                                                                              • Child Friendly
                                                                              • Air conditioning
                                                                              “Fabulous!!” We booked this beautiful house for our first week in the Keys. We had a group of adults and kids who went down for the week and we took our boat. This beautiful house had plenty of space for all of us and a ton of outside space to enjoy. T
                                                                              …see more

                                                                              Price per night from

                                                                              $245

                                                                              Price per night from

                                                                              $245