Where to stay in Islamorada, FL

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  • Post last modified:February 11, 2024
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Along the Overseas Highway in the Florida Keys, halfway from Miami to Key West, the Islamorada islands offer a tropical setting and the laid-back vibe you need to fully unwind. But where should you stay for the best experience?

Upper Matecumbe Key is the heart of the region, where you find several stunning resorts. In addition, other options for where to stay in Islamorada are Plantation Key, Windley Key and Lower Matecumbe Key.

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Plantation Key & Windley Key

The northernmost options for where to stay in Islamorada are Plantation Key and Windley Key. They welcome visitors to Islamorada in an appreciated fashion, offering that signature Florida Keys laidbackness.

A popular attraction on Windley Key is the Theater of the Sea. This popular marine park is home to a big number of animals including dolphins, sea lions, turtles and alligators.

You find many more Islamorada things to do just slightly further south on Upper Matecumbe Key. And courtesy of the Overseas Highway, it’s effortless to hop between Islamorada’s beautiful islands.

Pick Upper Matecumbe for: A northern base.

Blue boat, swaying palm tree, white sand and clear water — treasured features at Islamorada hotels
The peaceful Islamorada.

Upper Matecumbe Key

From the mainland, Upper Matecumbe Key is the third main Islamorada island. While it’s not at all like Duval Street in Key West (maybe thankfully), this centrally located island is the heart of activity in Islamorada.

On Upper Matecumbe, you find a good selection of restaurants, bars and shops. In addition, the island also has a small brewery scene and a surprising amount of galleries.

For an educational experience, visit the fascinating History of Diving Musuem where engaging stories are told with the help of historic equipment.

Pick Upper Matecumbe for: A livelier area.

Favorite location. It’s easy to see why Upper Matecumbe Key is such a popular option for where to stay when visiting Islamorada. The island offers everything you need for a superb stay in the Keys, including great hotels and resorts.

Islander Resort

Central on Upper Matecumbe Key, the beachfront Islander Resort is a very convenient place to stay. Just around the corner from the resort, you find many of the island’s restaurants and attractions.

But chances are that you never want to leave from here. The Islander Resort is like its own tropical bubble, with everything you need for a superb stay.

Sands of Islamorada

The basic Sands of Islamorada sits on the southern end of Upper Matecumbe Key. Right off the Overseas Highway and by the water, it’s a motel in Old Florida style. With comfy and nicely decorated rooms, you have found an excellent option for where to stay in Islamorada without breaking the bank.

Lower Matecumbe Key

Lower Matecumbe Key, just south of Upper Matecumbe Key, is the southernmost of the Islamorada islands. Slightly deeper into the Florida Keys, it’s an incredibly tranquil island, making it easier than ever to unwind.

There also are a few places to eat and have a drink on the island. However, the density of restaurants and things to do is much lower than on the neighboring Upper Matecumbe Key.

Still, a Lower Matcumbe highlight is legendary Robbie’s Marina. At the Florida Keys institution, you can eat good food, have a refreshing drink and even feed the hungry tarpons that gather at the dock.

Pick Lower Matecumbe for: Serenity.

Golden sunset in Islamorada
Sunset in Islamorada.

Where to stay in Islamorada FAQ

Where should I stay when visiting Islamorada?

No matter where you stay in Islamorada, you find a stunning environment and a peaceful ambience. However, Upper Matecumbe Key is the best place to stay if you want the ultimate access to the region’s restaurants, bars, shops and attractions. The island, with many great resorts, is the undisputed heart of the area.

Is Upper Matecumbe Key or Lower Matecumbe Key better?

Upper Matecumbe Key is where you find more restaurants, bars, shops and things to do. In contrast, Lower Matecumbe Key is significantly quieter. Don’t stress the choice too much: The Overseas Highway makes it very easy to travel between them.

Does Islamorada have a downtown?

The central area on Upper Matecumbe, near the Islander Resort, is sometimes referred to as Islamorada’s downtown. There you within walking distance find some of the island’s establishments, including restaurants and bars. But there’s nothing like the downtown area of Key West anywhere else in the Florida Keys.

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