Islamorada is located 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 to stay in Islamorada for the best experience?
Upper Matecumbe Key is the heart of the region where you find several stunning Islamorada resorts. In addition other options for where to stay in Islamorada are Plantation Key, Windley Key and Lower Matecumbe Key.
This travel site can exist thanks to compensation from advertising and affiliate links. Find out more here.
Find places to stay in Islamorada
Plantation Key & Windley Key, FL – Islamorada lodging on the northernmost islands
The northernmost options for where to stay in Islamorada are Plantation Key and Windley Key. They welcome visitors to Islamorada in an appreciated fashion.
All over Islamorada you find a peaceful ambience, and the first two keys are certainly no exception. Plantation Key and Windley Key offer the signature Islamorada laid-backness.
From Islamorada hotels on the northernmost islands it’s also easy to explore the rest of Islamorada. No matter where you stay in Islamorada, the Overseas Highway makes it easy to get around.
Still you find more things to do just slightly further south on Upper Matecumbe Key. So Plantation Key and Windley Key is not where in Islamorada you stay if you want to be surrounded by the area’s offerings.
But a very popular Islamorada attraction that you find on Windley Key is the Theater of the Sea. Above all the popular marine park is home to a big number of animals including dolphins, sea lions, turtles and alligators.
In short, Plantation Key and Windley Key are beautiful options for where to stay when visiting Islamorada. Although the islands are slightly away from the area’s hub of activity, it’s easy to get around within Islamorada.
Pick Upper Matecumbe for: Northernmost Islamorada lodging.
Upper Matecumbe Key, FL – Hotels and resorts in Islamorada’s heart
When you come from the mainland, Upper Matecumbe Key is the third main Islamorada island that you get to. Islamorada hotels on Upper Matecumbe Key give you a convenient base for enjoying the area.
The centrally located island is the heart of activity in Islamorada. It’s not at all like Duval Street in Key West. But if you look for an island with some liveliness, Upper Matecumbe is a superb choice.
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 the Islamorada island is home to the popular History of Diving Musuem. There visitors are welcome to learn everything there is to know about the diving history.
As the region’s main island Upper Matecumbe Key is also where you find many of the most popular places to stay in Islamorada. The island is home to everything from luxury Islamorada resorts to more simple Islamorada lodging.
To sum up, Upper Matecumbe Key is the perfect option for where to stay in Islamorada if you look for something that’s both laid-back and stimulating. At the island’s Islamorada places to stay you always have something fun to explore around the corner.
Pick Upper Matecumbe for: Islamorada hotels in 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 Islamorada hotels and resorts.
Recommended Islamorada hotels on Upper Matecumbe Key
Islander Resort – A phenomenal Islamorada resort
Central on Upper Matecumbe Key the beachfront Islander Resort is a very convenient place to stay in Islamorada. Just around the corner from the Islamorada resort you find the island’s restaurants and attractions.
But chances are that you never want to leave the phenomenal Islamorada resort. The place to stay in Islamorada is like its own tropical bubble, with everything you need for a superb stay.
Sands of Islamorada – Islamorada on a budget
Sands of Islamorada sits on the southern end of Upper Matecumbe Key. Right off the Overseas Highway and by the water it’s an Islamorada motel in Old Florida style.
If you look for a luxury, it’s not the best Islamorada place to stay for you. But with comfortable and well decorated rooms the motel is an excellent option for where to stay in Islamorada without breaking the bank.
Lower Matecumbe Key, FL – Islamorada lodging deeper into the chain
Lower Matecumbe Key, just south of Upper Matecumbe Key, is the southernmost of the Islamorada islands. It’s another popular option for where to stay in Islamorada.
Slightly deeper into the Florida Keys it’s an incredibly tranquil island. When you stay at Islamorada hotels or resorts on Lower Matecumbe Key, it’s 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.
But a Lower Matcumbe highlight when you stay in Islamorada is Robbie’s Marina. At the Florida Keys institution you can eat good food, have a refreshing drink or even feed the hungry tarpons at the dock.
All in all, Lower Matecumbe Key is an excellent option for where to stay in Islamorada if you look for something quiet. But if you rather stay on a livelier island you should look towards Islamorada hotels and resorts on Upper Matecumbe Key.
Pick Lower Matecumbe for: A quiet Islamorada stay.
Search for hotels in Islamorada, FL
Use the booking tool below to find the best places to stay in Islamorada. Browse the map for options in various areas, or click on the search button to get all Islamorada hotels listed.
Where to stay in Islamorada FAQ
Here you find the answers to some frequently asked questions about where to stay in Islamorada, FL.
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 in Islamorada if you want the ultimate access to the region’s restaurants, bars, shops and attractions. The island, with many great Islamorada resorts, is the undisputed heart of the area.
Upper Matecumbe Key is where you find more restaurants, bars, shops and things to do. In contrast, Lower Matecumbe Key is significantly quieter. Still the Overseas Highway makes it very easy to travel between the two islands with appreciated Islamorada lodging.
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.