Islamorada Rentals Are True Tropical Paradises

Islamorada rentals are beautiful destinations located in the Upper Florida Keys. This area is home to breathtaking beaches, Morada Bay, Worldwide Sports, and more. When you decide to spend your vacation in the Florida Keys, Islamorada is certainly an excellent place to stay.

Islamorada Rentals Are Great Ways to Explore the Island


Islamorada is a gorgeous location with numerous attractions and dining options. Travelers often have a great deal of fun exploring the island and each Islamorada condo rental is ideally located for this. Whether you are looking to enjoy freshly prepared local seafood, take a swim on the beach, or soak in the warm Florida sunshine, Islamorada, FL rentals on the beach are the perfect accommodations for your trip.

A Luxurious Islamorada Rental Awaits You


Islamorada house rentals are available in a number of different floor plans. Whether you seek a tiny rental property just perfect for a couple or are looking for a large villa for your entire family or group, you can find just the right Islamorada rental. Properties are all fully furnished, and many offer luxurious amenities such as private lanais, Florida rooms, swimming pools, spas, and more. Many Islamorada, FL rentals are located on resorts that offer a wide array of services and amenities to guests as well.

Islamorada, FL Rentals Offer Many Nearby Attractions


Islamorada rentals are near a number of attractions. Key Largo is only 20 minutes away and features the John Pennekamp Coral Reef Park. Other exciting attractions include the Everglades National Park and the Theater of the Sea dolphin show. Your Islamorada rental offers you easy access to all of the Florida Keys and is located near the mainland. Whether you are looking to see real, live alligators or take in the beauty of the Ocean and the Gulf, Islamorada, FL rentals are great accommodations. There is something available in the Florida Keys for every member of the family, and the properties are located in one of the most breathtakingly beautiful destinations in the world. The Florida Keys is a popular vacation spot, and Islamorada is a great location for people looking to enjoy the attractions yet still relax.

Expand your search for Florida vacation rentals to include Miami vacation rentals and Ft. Lauderdale rentals in South Florida, Destin vacation rentals and Siesta Key rentals on the Gulf Coast, or Orlando vacation home rentals near Disney.

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Islamorada: Houses, Condos & More(257)

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Paradise for Rent in the Florida Keys!! Designer Vacation Home on Deep Water
    3 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 7
$300 - $350
per night

Paradise for Rent in the Florida Keys!! Designer Vacation Home on Deep Water

3 night Minimum Stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
  1. Upper Florida Keys >
  2. Islamorada House
#330045
    (17)
    The Markeysa, the Ultimate Keys Experience - Private Beach
      4 Bedrooms,
    • 4 Bathrooms
      • , Sleeps 10
    $1,200
    per night

    The Markeysa, the Ultimate Keys Experience - Private Beach

    4 night Minimum Stay
    • 4 BR,
    • 4 BA,
    • Sleeps 10
    1. Upper Florida Keys >
    2. Islamorada House
    #40210vb
      (17)
      Cocomo's
        3 Bedrooms,
      • 4 Bathrooms
        • , Sleeps 14
      $857
      per night

      Cocomo's

      • 3 BR,
      • 4 BA,
      • Sleeps 14
      1. Upper Florida Keys >
      2. Islamorada House
      #969325
        (4)
        Oceanfront End Unit, Internet, Pool, Tennis, PANORAMIC OCEAN VIEWS
          2 Bedrooms,
        • 2 Bathrooms
          • , Sleeps 5

        Oceanfront End Unit, Internet, Pool, Tennis, PANORAMIC OCEAN VIEWS

        • 2 BR,
        • 2 BA,
        • Sleeps 5
        1. Upper Florida Keys >
        2. Islamorada Condo
        #151910
          (8)
          Bayfront with Free Dockage and Outstanding View!
            1 Bedrooms, Sleeps 4

          Bayfront with Free Dockage and Outstanding View!

          • 1 BR,
          • Sleeps 4
          1. Upper Florida Keys >
          2. Islamorada Condo
          #252520
            (6)
            Islamorada Waterfront-Great Dockage! Wonderful Views! WiFi & More!
              3 Bedrooms, Sleeps 8

            Islamorada Waterfront-Great Dockage! Wonderful Views! WiFi & More!

            • 3 BR,
            • Sleeps 8
            1. Upper Florida Keys >
            2. Islamorada House
            #223571
              (5)
              Islamorada Oceanfront Vacation Rental Home
                4 Bedrooms,
              • 3 Bathrooms
                • , Sleeps 10

              Islamorada Oceanfront Vacation Rental Home

              • 4 BR,
              • 3 BA,
              • Sleeps 10
              1. Upper Florida Keys >
              2. Islamorada House
              #114644vb
                1 Review
                Your Florida Keys Getaway.....
                  4 Bedrooms,
                • 4 Bathrooms
                  • , Sleeps 8

                Your Florida Keys Getaway.....

                • 4 BR,
                • 4 BA,
                • Sleeps 8
                1. Upper Florida Keys >
                2. Islamorada Estate
                #453867vb
                  Islamorada Oceanfront Estate 2 Lush Acres with Dockage Private
                    4 Bedrooms,
                  • 4 Bathrooms, 
                  • 1 Half Bath
                    • , Sleeps 12

                  Islamorada Oceanfront Estate 2 Lush Acres with Dockage Private

                  • 4 BR,
                  • 4 BA,
                  • 1 HF BA,
                  • Sleeps 12
                  1. Upper Florida Keys >
                  2. Islamorada House
                  #73619vb
                    1 Review
                    Ocean Front - Catch Bonefish &Tarpon from our 450-foot fishing pier.
                      4 Bedrooms,
                    • 3 Bathrooms
                      • , Sleeps 8

                    Ocean Front - Catch Bonefish &Tarpon from our 450-foot fishing pier.

                    • 4 BR,
                    • 3 BA,
                    • Sleeps 8
                    1. Upper Florida Keys >
                    2. Islamorada Lodge
                    #294142
                      Angler's Reef Coastal Conch Style Vacation Home in Islamorada, Fl.
                        2 Bedrooms,
                      • 2 Bathrooms, 
                      • 1 Half Bath
                        • , Sleeps 6
                      $195 - $285
                      per night

                      Angler's Reef Coastal Conch Style Vacation Home in Islamorada, Fl.

                      2 - 4 night Minimum Stay
                      • 2 BR,
                      • 2 BA,
                      • 1 HF BA,
                      • Sleeps 6
                      1. Upper Florida Keys >
                      2. Islamorada House
                      #944148
                        (14)
                        27 steps to Paradise Bay
                          2 Bedrooms,
                        • 1 Bathroom, 
                        • 1 Half Bath
                          • , Sleeps 6
                        $135 - $168
                        per night

                        27 steps to Paradise Bay

                        Book it Now!
                        6 night Minimum Stay
                        • 2 BR,
                        • 1 BA,
                        • 1 HF BA,
                        • Sleeps 6
                        1. Upper Florida Keys >
                        2. Islamorada Condo
                        #3488586
                          1 Review
                          Best Islamorada Vacation Rental
                            3 Bedrooms, Sleeps 6
                          $272
                          per night

                          Best Islamorada Vacation Rental

                          5 - 7 night Minimum Stay
                          • 3 BR,
                          • Sleeps 6
                          1. Upper Florida Keys >
                          2. Islamorada House
                          #153876
                            (26)
                            Mitchell's Keys Villa - Private, Secluded House on the Bay
                              2 Bedrooms, Sleeps 4

                            Mitchell's Keys Villa - Private, Secluded House on the Bay

                            • 2 BR,
                            • Sleeps 4
                            1. Upper Florida Keys >
                            2. Islamorada House
                            #236873
                              (60)
                              Magnificent Ocean View from Private Roof Top Sundeck!
                                2 Bedrooms,
                              • 2 Bathrooms, 
                              • 1 Half Bath
                                • , Sleeps 6

                              Magnificent Ocean View from Private Roof Top Sundeck!

                              • 2 BR,
                              • 2 BA,
                              • 1 HF BA,
                              • Sleeps 6
                              1. Upper Florida Keys >
                              2. Islamorada Townhome
                              #153551
                                (18)
                                Luxurious Home at Anglers Reef Oceanfront Resort with Boat Dock
                                  2 Bedrooms,
                                • 2 Bathrooms, 
                                • 1 Half Bath
                                  • , Sleeps 5

                                Luxurious Home at Anglers Reef Oceanfront Resort with Boat Dock

                                • 2 BR,
                                • 2 BA,
                                • 1 HF BA,
                                • Sleeps 5
                                1. Upper Florida Keys >
                                2. Islamorada House
                                #426200vb
                                  (11)
                                  Tropically Furnished Condo with Ocean Views
                                    2 Bedrooms,
                                  • 2 Bathrooms
                                    • , Sleeps 6
                                  $750 - $1,050
                                  per week

                                  Tropically Furnished Condo with Ocean Views

                                  7 night Minimum Stay
                                  • 2 BR,
                                  • 2 BA,
                                  • Sleeps 6
                                  1. Upper Florida Keys >
                                  2. Islamorada Condo
                                  #301565
                                    (11)
                                    Waterfront Paradise with Private Beach
                                      3 Bedrooms,
                                    • 2 Bathrooms
                                      • , Sleeps 10

                                    Waterfront Paradise with Private Beach

                                    • 3 BR,
                                    • 2 BA,
                                    • Sleeps 10
                                    1. Upper Florida Keys >
                                    2. Islamorada House
                                    #323488
                                      (10)
                                      Ocean Front Heated Pool w/Stunning ocean views,Tiki Hut Bar, 90' of Dockage
                                        3 Bedrooms,
                                      • 3 Bathrooms
                                        • , Sleeps 8

                                      Ocean Front Heated Pool w/Stunning ocean views,Tiki Hut Bar, 90' of Dockage

                                      • 3 BR,
                                      • 3 BA,
                                      • Sleeps 8
                                      1. Upper Florida Keys >
                                      2. Islamorada House
                                      #423195vb
                                        (10)
                                        Spectacular 3 Story Pool Home On Deep Dockage Minutes Ocean& Bay Tavernier Creek
                                          4 Bedrooms,
                                        • 3 Bathrooms
                                          • , Sleeps 8
                                        $700
                                        per night

                                        Spectacular 3 Story Pool Home On Deep Dockage Minutes Ocean& Bay Tavernier Creek

                                        1 - 14 night Minimum Stay
                                        • 4 BR,
                                        • 3 BA,
                                        • Sleeps 8
                                        1. Upper Florida Keys >
                                        2. Islamorada House
                                        #3014301
                                          Waterfront Rental at Florida Keys Resort!
                                            1 Bedrooms,
                                          • 1 Bathroom
                                            • , Sleeps 4
                                          $209 - $259
                                          per night

                                          Waterfront Rental at Florida Keys Resort!

                                          2 night Minimum Stay
                                          • 1 BR,
                                          • 1 BA,
                                          • Sleeps 4
                                          1. Upper Florida Keys >
                                          2. Islamorada Cottage
                                          #3491207
                                            2 Reviews
                                            Ocean Harbour- It Has It All for Your Keys Adventure MONTLY RENTAL
                                              3 Bedrooms,
                                            • 2 Bathrooms, 
                                            • 1 Half Bath
                                              • , Sleeps 8
                                            $7,000
                                            per month

                                            Ocean Harbour- It Has It All for Your Keys Adventure MONTLY RENTAL

                                            28 night Minimum Stay
                                            • 3 BR,
                                            • 2 BA,
                                            • 1 HF BA,
                                            • Sleeps 8
                                            1. Upper Florida Keys >
                                            2. Islamorada Condo
                                            #3478902
                                              A Beauty on Two Converging Crystal Clear Canals
                                                4 Bedrooms, Sleeps 12

                                              A Beauty on Two Converging Crystal Clear Canals

                                              • 4 BR,
                                              • Sleeps 12
                                              1. Upper Florida Keys >
                                              2. Islamorada House
                                              #223159vb
                                                Luxury! Bayside - 3 BR - Paradise in the Keys with Boat Slip
                                                  3 Bedrooms,
                                                • 2 Bathrooms, 
                                                • 1 Half Bath
                                                  • , Sleeps 8

                                                Luxury! Bayside - 3 BR - Paradise in the Keys with Boat Slip

                                                • 3 BR,
                                                • 2 BA,
                                                • 1 HF BA,
                                                • Sleeps 8
                                                1. Upper Florida Keys >
                                                2. Islamorada Townhome
                                                #108057vb
                                                  Dream Home in the Keys with Heated Pool Legal Weekly Rental
                                                    5 Bedrooms, Sleeps 12

                                                  Dream Home in the Keys with Heated Pool Legal Weekly Rental

                                                  • 5 BR,
                                                  • Sleeps 12
                                                  1. Upper Florida Keys >
                                                  2. Islamorada House
                                                  #12740vb
                                                    (8)
                                                    Peaceful Bay front with pool, jacuzzi and outdoor sports. Relax by the pool!
                                                      3 Bedrooms,
                                                    • 3 Bathrooms
                                                      • , Sleeps 8

                                                    Peaceful Bay front with pool, jacuzzi and outdoor sports. Relax by the pool!

                                                    • 3 BR,
                                                    • 3 BA,
                                                    • Sleeps 8
                                                    1. Upper Florida Keys >
                                                    2. Islamorada Estate
                                                    #383318
                                                      Florida Keys Islamorada Deep Water Dockage Best Value in Keys
                                                        3 Bedrooms,
                                                      • 2 Bathrooms
                                                        • , Sleeps 7
                                                      $250 - $400
                                                      per night

                                                      Florida Keys Islamorada Deep Water Dockage Best Value in Keys

                                                      3 night Minimum Stay
                                                      • 3 BR,
                                                      • 2 BA,
                                                      • Sleeps 7
                                                      1. Upper Florida Keys >
                                                      2. Islamorada Townhome
                                                      #221210
                                                        (9)
                                                        Keys home in Anglers Reef with ocean view, dock, comm. pool & beach
                                                          2 Bedrooms,
                                                        • 2 Bathrooms, 
                                                        • 1 Half Bath
                                                          • , Sleeps 6
                                                        $1,800 - $2,100
                                                        per week

                                                        Keys home in Anglers Reef with ocean view, dock, comm. pool & beach

                                                        7 night Minimum Stay
                                                        • 2 BR,
                                                        • 2 BA,
                                                        • 1 HF BA,
                                                        • Sleeps 6
                                                        1. Upper Florida Keys >
                                                        2. Islamorada House
                                                        #3000700
                                                          (7)
                                                          The We Key House
                                                            2 Bedrooms,
                                                          • 1 Bathroom
                                                            • , Sleeps 5
                                                          $170 - $190
                                                          per night

                                                          The We Key House

                                                          6 night Minimum Stay
                                                          • 2 BR,
                                                          • 1 BA,
                                                          • Sleeps 5
                                                          1. Upper Florida Keys >
                                                          2. Islamorada Cottage
                                                          #3486149
                                                            2 Reviews
                                                            Beautiful New Waterfront Home In Port Antigua
                                                              3 Bedrooms,
                                                            • 3 Bathrooms
                                                              • , Sleeps 8

                                                            Beautiful New Waterfront Home In Port Antigua

                                                            • 3 BR,
                                                            • 3 BA,
                                                            • Sleeps 8
                                                            1. Upper Florida Keys >
                                                            2. Islamorada House
                                                            #178832
                                                              (3)
                                                              • 1 - 30 of 257
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