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Explore Islamorada from Your Luxury Lodging

Luxury rental homes are available in Islamorada, Florida, with up to five bedrooms that will accommodate a dozen people in comfort and style. Many of these residences are oceanfront, and you can even find one that includes your own private fishing pier and swimming pool. Linens are provided, and each dwelling includes a washer and dryer. The homes are beautifully furnished and come with completely outfitted kitchens.

Eco-tours

Tour companies in Islamorada offer a variety of walking and boating tours. An eco-tour will give you a chance to see the gorgeous natural scenery of the Florida Keys up close. The Indian Key walking tour combines land and sea, with a twenty-minute kayak ride to the beautiful and unspoiled island of Indian Key. The tour includes a narrated description of the rich history of this unique island.

Water Sports

There are a lot of options when it comes to water sports in Islamorada. Jets ski and boat rentals are available, and there are plenty of guided boat tours. Fishing, diving and snorkeling gear can be rented, along with transportation to locations like Alligator Reef, a marine sanctuary filled with sea life. Reservations are recommended to make sure that the equipment you need will be available.

Sport Fishing

Islamorada has the largest sport fishing fleet in the Florida Keys. Fishing tournaments are held there every year, with bonefish and sailfish being the main objects of pursuit. Fishing excursions are offered for visitors, and some restaurants will even cook your catch for a small fee.

Dining and Nightlife

Local Restaurants

No matter what kind of food you prefer, you can find it at one of the many popular restaurants on Islamorada. Naturally, seafood is the specialty, but restaurants like the M.E.A.T. Eatery and Taproom also offer delicious burgers and steaks along with pulled pork. Chef Michael's offers upscale dining for lunch or dinner, and their ceviche is one of the house specialties. The menu also offers delicious crab soup and lobster tempura.

Local Music Scene

The nightlife on Islamorada is low-key and laid-back, with a tropical vibe. Florida Keys Brewing Company and Islamorada Fishing Club are two of the popular spots for kicking back with a craft brew or a frozen drink. Lazy Days Restaurant and Sharkey's Pub and Galley offer live, local music in the evening.

Weather

Islamorada is sunny and warm just about year-round. Temperatures in the winter range from the mid-sixties to the high seventies, and the thermometer rarely tops ninety degrees in the summer. Spring and fall are the best times to visit because it's warm enough to lie on the beach but not too hot to enjoy outdoor activities. From the beginning of October to the end of May, there are very few rainy days.

How to Get There

To reach Islamorada by plane, it's best to fly into the Miami or Ft. Lauderdale airport. Once you arrive, there are several car and van rental companies to choose from. Shuttles also operate from the airport to Islamorada and other locations in the Florida Keys. Some of them provide luxuries like mini-bars, and all of them are air-conditioned.

If you are driving, take Exit 4 from the Florida Turnpike. This will connect you to Route U.S. 1, a highway that extends all the way through the Keys. But be careful, because speed limits are enforced in the area. Greyhound Bus also provides a shuttle to the Keys, and this is a picturesque way to see the sights along the way.

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Islamorada: Houses, Condos & More (900+)

  • 1 - 50 of 900+
Additional fees apply. Taxes may be added.
    NEW!
    • 2 BR
    • 2 BA
    • 1 HF BA
    • Sleeps 6
    1 Review
      Exceptional! 5.0/5
      (28 reviews)
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      • 1 BR
      • 1 BA
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      28
        • 3 BR
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          Wonderful! 4.8/5
          (16 reviews)
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            NEW!
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              • Sleeps 6
              11
                Wonderful! 4.9/5
                (46 reviews)
                $73
                avg/night
                • Studio
                • 1 BA
                • Sleeps 2
                46
                  Wonderful! 4.8/5
                  (41 reviews)
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                  • 2 BR
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                  41
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                    30
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                      5
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                        15
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                            36
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                              31
                                Wonderful! 4.9/5
                                (26 reviews)
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                                  Exceptional! 5.0/5
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                                      Exceptional! 5.0/5
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                                            Excellent! 4.4/5
                                            (5 reviews)
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                                                NEW!
                                                • 2 BR
                                                • 2 BA
                                                • 1 HF BA
                                                • Sleeps 6
                                                  Wonderful! 4.9/5
                                                  (12 reviews)
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                                                  • 1 BA
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                                                  12
                                                    Wonderful! 4.9/5
                                                    (28 reviews)
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                                                      Wonderful! 4.9/5
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                                                                    Exceptional! 5.0/5
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                                                                    5
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                                                                        Exceptional! 5.0/5
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                                                                              2 Reviews
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                                                                                7
                                                                                  Excellent! 4.7/5
                                                                                  (23 reviews)
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                                                                                  • 4 BR
                                                                                  • 3 BA
                                                                                  • Sleeps 12
                                                                                  23
                                                                                    Exceptional! 5.0/5
                                                                                    (19 reviews)
                                                                                    View details for price
                                                                                    • 4 BR
                                                                                    • 5 BA
                                                                                    • Sleeps 10
                                                                                    19
                                                                                      Exceptional! 5.0/5
                                                                                      (5 reviews)
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                                                                                        15
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • 1 HF BA
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                                                                                          9
                                                                                            Wonderful! 4.8/5
                                                                                            (20 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 6
                                                                                            20
                                                                                              • 3 BR
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                                                                                              1 Review
                                                                                                • 3 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 8
                                                                                                1 Review
                                                                                                  Wonderful! 4.8/5
                                                                                                  (9 reviews)
                                                                                                  avg/night
                                                                                                  • 1 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 4
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                                                                                                    8
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                                                                                                      • 1 - 50 of 900+
                                                                                                       

                                                                                                      Recent Islamorada Reviews

                                                                                                      Great Stay!

                                                                                                      5 of 5
                                                                                                      We had a great stay in the Angler's Reef. Lisa is a wonderful host and helped immediately, whenever we contacted her. Lisa's house is directly located in the 2nd row, which makes it very close to swimming pool and beach, but at the same time quite as distanced from the street. The house is very nicely decorated and spotless. Beds are wonderful comfortable. We liked it so much, we even extended our stay. Definitely a recommendation, if you want to stay in the Keys.
                                                                                                      • Submitted: Sep 13, 2016
                                                                                                      • Stayed: Aug 2016

                                                                                                      Great location on the ocean side of Islamorada!

                                                                                                      5 of 5
                                                                                                      The house is close to the water so you get the ocean breeze. The available dock is very close to the house so easy to load diving equipment and fishing gear. The house is clean and has a good flow. The showers are strong. The front deck is perfect to sit and read in the shade after spending the day on the ocean The back deck has ocean view and perfect for a glass of wine before diner. Will be back...
                                                                                                      • Submitted: Sep 7, 2016
                                                                                                      • Stayed: Aug 2016

                                                                                                      Wonderful rental!!!

                                                                                                      5 of 5
                                                                                                      Gracious hosts in David and Ginette. Great condo. Nice quiet location. Beautifully decorated. Very comfortable. Would love to visit again in the future!! No complaints
                                                                                                      • Submitted: Aug 13, 2016
                                                                                                      • Stayed: Jul 2016