Islamorada, FL

Travel Guide

A beach with palm trees and white lounge chairs under a clear blue sky.
A beach with white lounge chairs, a covered pavilion, and palm trees.
A wooden dock extending into calm waters, surrounded by sandy beach and palm trees.
A waterfront with palm trees, a dock, and a small boat.
A colorful shop with various fish decorations, a sign that says "You bring the tequila, I'll bring the bad decisions," and a display of mugs and other items.

This idyllic island community is one of the most luxurious in the Florida Keys and is a great destination for scuba diving and game fishing.

The tropical Islamorada Keys are home to many luxurious resorts, so take your pick and spend your days lazing in the sun, diving through shipwrecks or cruising the Gulf of Mexico for the biggest fish in the sea. In addition to sailing, game fishing, sunning and diving, the community of cosmopolitan residents love their art and gourmet food.

Begin your time on the Islamorada Keys with a stroll down U.S. Route 1, the highway connecting the Keys. Visit boutique retail outlets, galleries and the 1935 Hurricane Memorial.

Islamorada’s sub-tropical climate means that both the air and the water remain warm year-round, making it the ideal breeding and feeding ground for countless species of fish. Whether you want to spend the day on board a luxury charter boat or prefer bobbing on the gentle seas in a small motorboat, the marina of Founders Park is the place to start.

Islamorada offers scuba diving classes for beginners. Afterward, visit the History of Diving Museum to learn all about this adventurous hobby. Organize a scuba diving or snorkeling trip to some of Florida’s most lauded dive sites to see the fish in their natural habitat. Popular spots include the Eagle, a shipwreck just off the coast and the Conch Wall, a gently sloping rock shelf. If you’d rather stay dry, visit the Theater of the Sea to watch dolphins perform at the aquarium.

Pick up tackle and rent rods from one of the angling specialists in town. Islamorada has developed a reputation for being one of the best fishing destinations in North America. Game fish the size of outstretched arms are commonplace, so you won’t even have to exaggerate about your catch of the day.

Islamorada can be reached from downtown Miami in just 90 minutes by car or by boat from the neighboring Keys. Accommodations range from luxury resorts to cozy bungalows near Anne’s Beach, a scenic public stretch of coast.

Where to stay in Islamorada

Find the best Islamorada areas and neighborhoods for the activities you enjoy most. Learn more about Islamorada
Learn more about Islamorada

Matecumbe

If you're spending some time in Matecumbe, Bud n' Mary's Dive Center and Robbie’s of Islamorada are top sights worth seeing.

Lower Matecumbe Beach

Though Lower Matecumbe Beach might not have many top sights, you can venture to the surrounding area to see attractions like Anne's Beach and Sunset Drive Beach.

Venetian Shores

Venetian Shores might not have many top sights, but Rain Barrel Village and Founders Park are two attractions nearby that you can check out.

Seabreeze Trailer Park

If you're looking for some top things to see and do in Seabreeze Trailer Park and surrounding area, you can visit Founders Park and Islamorada County Park.

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is $261 total per night from Oct 21 to Oct 22
$261 total
per night
Oct 21 - Oct 22
Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is $197 total per night from Oct 26 to Oct 27
$197 total
per night
Oct 26 - Oct 27
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
9.4/10 Exceptional! (1,795 reviews)
"Great location"

Reviewed on Oct 16, 2026

Chesapeake Beach Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
The price is $310 total per night from Nov 15 to Nov 16
$310 total
per night
Nov 15 - Nov 16
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
9.4/10 Exceptional! (1,143 reviews)
"Very nice experience and cosy hotel in the Keys, super recommended!"

Reviewed on Oct 16, 2026

Islander Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway Islamorada FL
Book a stay at this beach aparthotel in Islamorada. Enjoy free WiFi, a beach locale, and a marina. Our guests praise the helpful staff and the clean rooms in ...
Breezy Palms Resort
Treasure Harbor

Treasure Harbor

3 out of 5
200 Treasure Harbor Dr Islamorada FL
Stay at this houseboat in Islamorada. Enjoy free WiFi, free parking, and premium bedding. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (179 reviews)
"The boat was very clean and included all the amenities we needed. The air conditioning worked very well. The host was extremely accommodating with our very late check-in and early departure. I would definitely recommend!"

Reviewed on Oct 15, 2026

Treasure Harbor
Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay

3 out of 5
73801 Overseas Hwy Islamorada FL
Stay at this condo in Islamorada. Enjoy free WiFi, free parking, and a marina. Popular attractions Anne's Beach and Sunset Drive Beach are located nearby.
9/10 Wonderful! (17 reviews)
"Very clean efficiency with a full fridge, stove and oven. Grills by the water to cook your own catch or from the market down the road. Large pool, well maintained."

Reviewed on Oct 15, 2026

Caloosa Cove Resort by CoolVacay
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Islamorada attractions

Things to do

Frequently asked questions

Is Islamorada worth visiting?
Islamorada is worth visiting for its beautiful outdoor attractions, including Lignumvitae Key Botanical State Park and Anne's Beach. Travelers can also explore the distinct Matecumbe area and enjoy a variety of dining options, with fresh seafood and North American cuisine readily available.
When is the best time to visit Islamorada?
The best time to visit Islamorada is from February through April, when the weather is typically pleasant for enjoying the destination. For travelers seeking fewer crowds and better value, the quieter months of October through December are a good option, offering a more relaxed experience.
Where are the best neighborhoods to explore in Islamorada?
The best neighborhoods to explore in Islamorada depend on what you want to see:

  • Matecumbe offers access to beaches like White Marlin Beach, Coral Cove, and Toll Gate Shores.

What is Islamorada known for?
Islamorada is known for its natural attractions like Lignumvitae Key Botanical State Park and Anne's Beach. Travelers can also explore Robbie's of Islamorada for unique experiences. The area, including neighborhoods such as Matecumbe, also offers a vibrant seafood food culture.
What is a good itinerary length for Islamorada?
A good itinerary length for Islamorada is two to three days to enjoy Anne's Beach, visit Robbie's of Islamorada, and take a Waverunner Tour. For a longer trip of four to five days, you can explore Lignumvitae Key Botanical State Park, enjoy a Sunset Eco-Cruise, and discover the Matecumbe area. See Islamorada Activities.
What are the top things to do in and around Islamorada?
Islamorada offers beautiful natural spots and exciting water adventures for travelers:

  • Explore Lignumvitae Key Botanical State Park.
  • Relax at Anne's Beach.
  • Visit Robbie's of Islamorada.
  • Take a Waverunner tour to see Mangrove Tunnels, islands, and a sandbar.
  • Enjoy a private ecotour and snorkeling boat tour.

How do I plan a trip to Islamorada?
To plan your trip to Islamorada, book flights and hotels in advance. Consider staying in Matecumbe to be near White Marlin Beach. Book activities like a Waverunner Tour or Sunset Eco-Cruise, and explore attractions such as Anne's Beach and Robbie's of Islamorada. Plan outdoor activities for early morning or late afternoon. A rental car will help you get around.
What cuisines can you find in Islamorada?
In Islamorada you can find Cuban cuisine, with dishes like Ropa Vieja, Cuban sandwiches, and plantains. Travelers can also enjoy fresh seafood, North American favorites, and European options including Mediterranean and Italian dishes, as well as other Latin American flavors.
Can I book a refundable hotel in Islamorada?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Islamorada by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Islamorada with Expedia?
Expedia makes it easier to plan your Islamorada trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Islamorada?
The best choice depends on your travel style. Hotels in Islamorada can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Islamorada trip on Expedia?
Once you've booked your Islamorada trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Islamorada trip?
Expedia offers customer support before, during, and after your Islamorada trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Islamorada?
If it's your first trip to Islamorada, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Islamorada hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Islamorada hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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