Islamorada Travel Guide

Tourist 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. Organise 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 Theatre 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. Accommodation range from luxury resorts to cosy bungalows near Anne’s Beach, a scenic public stretch of coast.

Our guide on where to stay in Islamorada

Find the best Islamorada areas 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

While Lower Matecumbe Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Anne's Beach and Sunset Drive Beach.

Venetian Shores

Though Venetian Shores may not have many top sights, you can venture to the surrounding area to see attractions like Founders Park and Windley Key Fossil Reef Geological State Park.

Seabreeze Trailer Park

While there might not be top attractions in Seabreeze Trailer Park, you can explore the larger area and discover places like 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 NZ$405 per night from 29 Sept to 30 Sept
NZ$405
29 Sept - 30 Sept
includes taxes & fees
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 in their ...
9.2/10 Wonderful! (1,456 reviews)
"The staff was very accommodating and nice. The room however needed an upgrade. The bed squeaked every time someone moved and the beds were curved in the middle. For the price, I was expecting so much more! You pay for the amenities at the resort, not the room."

Reviewed on 25 Sept 2026

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is NZ$378 per night from 29 Sept to 30 Sept
NZ$378
29 Sept - 30 Sept
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...
9.2/10 Wonderful! (1,783 reviews)
"I liked the breakfast. One pool was being worked on and the pool workers helped themselves to the free breakfast. Some of them stood in the coffee and drink area and ate their free breakfast. The tree trimmers took up some of relaxing areas and they were noisy. The cleaning staff and the front desk ..."

Reviewed on 25 Sept 2026

Chesapeake Beach Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

4 out of 5
84001 Overseas Hwy Islamorada FL
The price is NZ$541 per night from 15 Oct to 16 Oct
NZ$541
15 Oct - 16 Oct
includes taxes & fees
Stay at this beach resort in Islamorada. Enjoy free Wi-Fi, 3 outdoor pools and 4 restaurants. Our guests praise the helpful staff and the clean rooms in their ...
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio 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
Stay at this beach aparthotel in Islamorada. Enjoy free Wi-Fi, a beach locale and a marina. Our guests praise the helpful staff and the clean rooms in their ...
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 Wi-Fi, free parking and premium bedding. Our guests praise the helpful staff in their reviews. Popular attractions ...
9/10 Wonderful! (175 reviews)
"Amazing location and well equipped. Loved the local vibe, didn't see a manatee but plenty of green iguanas. Property was comfortable with great AC."

Reviewed on 9 Sept 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 Wi-Fi, free parking and a marina. Popular attractions Anne's Beach and Sunset Drive Beach are located nearby.
8.8/10 Excellent! (14 reviews)
"The fact we were never told the restaurant and bar were closed and the property was undergoing yearly renovations was just a lousy way to conduct business. We had to take Ubers all day just to get breakfast and lunch. If we were told we would have never booked. Spent a ton in rides since there is ..."

Reviewed on 21 Sept 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.

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