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.

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 NT$6,034 per night from Oct 13 to Oct 14
NT$6,034
NT$9,123 total
Oct 13 - Oct 14
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 ...
Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is NT$4,822 per night from Oct 14 to Oct 15
NT$4,822
NT$7,221 total
Oct 14 - Oct 15
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! (1,796 reviews)
"Un lugar muy tranquilo y una vista hermosa. Excelente para relajarse, meditar y descansar."

Reviewed on 2026/10/10

Chesapeake Beach Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
The price is NT$8,333 per night from Oct 18 to Oct 19
NT$8,333
NT$11,709 total
Oct 18 - Oct 19
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. ...
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 ...
9/10 Wonderful! (765 reviews)
"This fun little place was a great stopover on our way to Key West. This is not a new property, but it has been redone so well. We stayed in a bungalow and were really struck by how well it had been renovated. Great vibe and decor."

Reviewed on 2026/10/11

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! (178 reviews)
"They bent over backwards for us, we enjoyed the stay. Everyone should try it."

Reviewed on 2026/10/10

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.
8.8/10 Excellent! (15 reviews)
"Caloosa Cove is well located for exploring both Islamorada as well as the lower keys. The room was clean and spacious and had a very usable kitchen. The balcony in the room offered unobstructed views of the ocean and pool area. The pool was large and also had a great view of the ocean. The only criticism ..."

Reviewed on 2026/10/10

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

Cities near Islamorada