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Top Hotels in Islamorada

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Things to do in Islamorada

Long Key State Park
Hurricane Monument
Theater of the Sea

How much are hotels near Long Key State Park?

If you’re planning on staying at any of momondo’s recommended hotels in the area of Islamorada nearest to Long Key State Park, you should expect to pay around $338/night. This price fluctuates based on time of year. In general, a rate under $338/night is a good deal for momondo users staying near Long Key State Park. Hotels near Long Key State Park are typically 14% more expensive than the average hotel in Islamorada, which is $289.

Hotels near Long Key State Park

How much are hotels near Hurricane Monument?

Below are the 12 user recommended hotels in the area of Islamorada that is closest to Hurricane Monument. The average price near Hurricane Monument is $338/night, with prices varying based on several factors including time of year. Hotels near Hurricane Monument are typically 14% more expensive than the average hotel in Islamorada, which is $289.

Hotels near Hurricane Monument

How much are hotels near Theater of the Sea?

If you’re looking for a hotel in Islamorada near Theater of the Sea then you are in luck. momondo recommends 12 hotels near Theater of the Sea and on average, area hotels cost $338/night. This price may vary based on season. Hotels near Theater of the Sea are typically 14% more expensive than the average hotel in Islamorada, which is $289.

Hotels near Theater of the Sea

When to book a hotel in Islamorada

Check out the information below to find the best deal on a Islamorada hotel room
Low Season
High Season

cheapest month to stay


expected price decrease

most expensive time to stay


expected price increase

$220 - $472
Highest day of week
Cheapest day of week

av. price over the last two weeks

Average price (weeknight)


av. price over the last two weeks

av. price over the last two weeks

Average price (weekend night)


av. price over the last two weeks

Cheapest time to book
The cheapest time to book hotels in Islamorada is: 3 star, 83 days before. 4-5 star, on the same day that your stay begins.
1-2 star
$204 - $228
3 star
$239 - $296
4-5 star
$335 - $459

Islamorada travel tips

Let us help you with the best tips about Islamorada

Which neighborhoods in Islamorada should I stay in if I want access to public transport?

Islamorada has a very limited public transport system, but because it's so small, it's easy to navigate on foot. However, for convenient island hopping, consider renting a car, available through momondo. There are buses that run along the main road from Miami down through the Florida Keys, known as the Overseas Highway. These include the Route 301 Dade-Monroe Express between Miami and Marathon, and the Greyhound bus between Miami and Key West, which stops at Burger King on Upper Matecumbe Key. Some taxis are available, as well as ridesharing services. Some hotels in Islamorada may offer a shuttle service, it is recommending to check with the concierge or at the check-in desk. If you’re feeling energetic and you want to check out the range of hotels in Islamorada, why not rent a bicycle? The neighborhood of Matecumbe, on Upper Matecumbe Key, has the greatest concentration of Islamorada hotels, including the Caribbean Resort, Hadley House Islamorada and the La Siesta Resort & Marina. Another neighborhood is Lower Matecumbe Beach, but this key has fewer Islamorada hotels. Also, since this is the Florida Keys, you may not find too many cheap hotels in Islamorada.

How much does a hotel in Islamorada cost per night?

Use the information below to find quality Islamorada hotel rooms for low prices
2 stars and under
Chesapeake Beach Resort
#1 Most popular

Chesapeake Beach Resort



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La Jolla Resort
Best value

La Jolla Resort



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3 stars
Amara Cay Resort
#1 Most popular

Amara Cay Resort



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Lime Tree Bay Resort
#2 Most popular

Lime Tree Bay Resort



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Fisher Inn Resort & Marina
Best value

Fisher Inn Resort & Marina



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4 stars +
Cheeca Lodge & Spa
Best value

Cheeca Lodge & Spa



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Best prices found by momondo users in the past 24 hours.

Hostels and cheap hotels in Islamorada

These hotels and hostels usually make for a cheap way to stay in Islamorada

Get the best value hotel in Islamorada

These hotels have the best prices for their ratings

Where to stay in Islamorada

What neighborhoods in Islamorada should I stay in based on why I’m traveling?

Upper and Lower Matecumbe Keys are great options for the widest range of hotels in Islamorada. Casa Morada on Upper Matecumbe Key, with its private man-made island, is ideal for newlyweds or couples looking to add some romance to their trip or put the spark back in their marriage. If you’re on holiday to decompress, Caloosa Cove Resort & Marina, close to Anne’s Beach on Lower Matecumbe Key, is an option for people wanting to relax, unwind and get away from it all.

Learn about attractions and sights in Islamorada

What are the most popular attractions in Islamorada?

Theater of the Sea on Windley Key, just north of Upper Matecumbe Key, offers live dolphin, sea lion and parrot shows, as well as interactions with sea turtles, sharks, alligators and rays. Animals here are carefully cared for and trained, and money earned is raised for animal rescue and rehabilitation, in order to preserve the marine life ecosystems of the Florida Keys. Anne’s Beach on Lower Matecumbe Key is a scenic beach with a shallow swimming area that also has picnic tables, a boardwalk and bathroom facilities. This area is known as the sportfishing capital of the world, so when looking to book hotels in Islamorada, keep that in mind. Try Bud N’ Mary’s Marina on Upper Matecumbe Key, near the Islamorada Boat Ramp.

Which neighborhoods in Islamorada have a large selection of bars and restaurants?

Both Upper Matecumbe Key and Lower Matecumbe Key have a number of establishments. The Overseas Highway is where most eateries are to be found. Highly recommended are Lazy Days Restaurant and Wahoo’s Bar and Grill Restaurant, both on the Overseas Highway. Wahoo’s is on the northern side of Upper Matecumbe Key on the way to Windley Key, while Lazy Days is on the southern side on the way to Lower Matecumbe Key. Habanos Oceanfront Dining, right near Anne’s Beach on Lower Matecumbe Key, offers casual Cuban fare. Lorelei Restaurant & Cabana Bar, near the Islamorada Fishing Club on Upper Matecumbe Key, also comes highly recommended for casual seafood. It is on Madeira Rd, close to the Greyhound bus stop (which is at Burger King, if you feel like some fast food). Unless you have rented a car for travel between the keys, you might want to eat close to your hotel in Islamorada so you can walk to your meals.

What popular events take place in Islamorada?

The annual Island Fest, presented by the Islamorada Chamber of Commerce, usually takes place in the spring and includes arts and crafts, gourmet cuisine, vintage cars and live music. It happens at Founders Park near the Plantation Yacht Harbor Marina on Plantation Key. It’s just off the Overseas Highway (US Route 1), so if you’re on a bus between Key West and Miami, jump off here.

Islamorada travel information

How long do people stay in Islamorada?

3 nights is the typical length of stay for people visiting Islamorada.

How much does a hotel cost in Islamorada?

The price of a hotel in Islamorada depends on several factors such as star rating, location and demand. Generally speaking, the average cost of a hotel is around $283 per night.

When is the best time to book a hotel in Islamorada?

Room prices for hotels in Islamorada can be as much as 36% lower in the month of September. So this is a great time to book and save money.

Which day is cheapest to stay in Islamorada?

Tuesday is the cheapest day for hotel rooms in Islamorada. Friday is the most expensive day.

How much does a hostel in Islamorada cost?

On average, a hostel in Islamorada will be priced around $220. This price will be per person, per night and was obtained using hostel and 2 star or below hotels. In comparison, this will be $63 lower than your typical Islamorada hotel.

Based on the weather in Islamorada, what attractions are popular during December?

Temperatures in Islamorada are typically around 71.6 °F during December and the chance of rain is low, which makes December the perfect time to spend some time outside at popular area attractions like Las Olas Beach, Siesta Beach, and Venice Beach.