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 Founders Park and Windley Key Fossil Reef Geological State 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$6,265 per night from May 28 to May 29
NT$6,265
NT$8,823 total
May 28 - May 29
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! (1,732 reviews)
"We love this hotel. The breakfast was great and the amenities were excellent and the staff was friendly polite and knowledgeable. They were great. We are from Texas and whenever we come back this way we definitely will stay here. We tell everybody about this hotel."

Reviewed on 2026/5/24

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$7,541 per night from May 31 to Jun 1
NT$7,541
NT$10,792 total
May 31 - Jun 1
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)
"amenities were great, clean hotel, lots of fun."

Reviewed on 2026/5/24

Cheeca Lodge & Spa
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
The price is NT$7,531 per night from May 31 to Jun 1
NT$7,531
NT$10,603 total
May 31 - Jun 1
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. ...
9.4/10 Exceptional! (1,017 reviews)
"Absolutely beautiful property, clean and well maintained. Staff was super friendly and there was lots of complimentary activities for the whole family. 10/10 we will absolutely be back."

Reviewed on 2026/5/24

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.
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! (682 reviews)
"Good"

Reviewed on 2026/5/24

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 ...
9.6/10 Exceptional! (76 reviews)
"I am not usually about leaving reviews however this property definitely needs it. Heard a lot about being pampered when I was checked in and that they will bring you anything and to let them know what our needs were. Property does not have any coffee shop or restaurant. We were told we could come ..."

Reviewed on 2026/5/18

The Islands of Islamorada
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.
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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