Islamorada, FL

Travel Guide

Islamorada
Islamorada
Islamorada
Islamorada
Islamorada

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

Matecumbe

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.

Matecumbe
Colorful Island Palm Tree Sunset

Venetian Shores

Venetian Shores might not have many top sights, but Windley Key Fossil Reef Geological State Park and Islamorada County Park are two attractions nearby that you can check out.

Venetian Shores
Anne’s beach is on Lower Matecumbe Key

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.

Lower Matecumbe Beach
Coastline of Islamorada, panoramic view at dusk

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.

Seabreeze Trailer Park
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is NT$6,257 per night from May 10 to May 11
NT$6,257
NT$8,812 total
May 10 - May 11
includes taxes & fees
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. ...
9.2/10 Wonderful! (1,704 reviews)
Super clean, we stayed in a 1 bdrm villa, ocean view. Recently updtd. Staff, anyone we ran into were so nice. April 18 - 25th, no crowds whatsoever there during our stay of 7 nights.

Reviewed on 2026/4/25

Chesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is NT$9,422 per night from May 3 to May 4
NT$9,422
NT$12,905 total
May 3 - May 4
includes taxes & fees
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 ...
9.2/10 Wonderful! (1,314 reviews)
Everything

Reviewed on 2026/4/24

Cheeca Lodge & Spa
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
The price is NT$8,314 per night from May 3 to May 4
NT$8,314
NT$11,481 total
May 3 - May 4
includes taxes & fees
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. ...
9.2/10 Wonderful! (1,004 reviews)
Perfect for a few days! In such a good location to be able to explore a lot of places outside of the resort property and tucked away from the main road.

Reviewed on 2026/4/24

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.
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! (150 reviews)
Place was as described. Only thing i would recommend is a little more attention to detail during turnover cleaning as we found nail clippings and foot splatter on the wall. We loved the setting after our long days being able to be on the water, had manatees swim by us a couple times. Still recommend ...

Reviewed on 2026/4/16

Treasure Harbor
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 ...
8.8/10 Excellent! (664 reviews)
Room was very clean and the bed was fantastically comfortable! Furniture was a bit out dated and not as comfortable as I would have liked. Pool was fantastic as well!

Reviewed on 2026/4/26

Breezy Palms Resort
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy Islamorada FL
Book a stay at this beach villa in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada ...
9.8/10 Exceptional! (74 reviews)
What a wonderful venue for our last 2 nights in the Keys. This place is a hidden gem. The entire staff, especially Edith, the bartender, were fantastic.

Reviewed on 2026/4/14

The Islands of Islamorada
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.

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