Living Island Life in Islamorada

The Florida Keys are a chain of 1,700 islands at the southeastern tip of Florida, and include the country's southernmost point. The islands lie along the Florida Straits, dividing the Atlantic Ocean to the east from the Gulf of Mexico to the west. Home to North America's only living coral barrier reef, the Florida Keys are world renown for their scuba diving, snorkeling and sport-fishing.

Islamorada, meaning 'village of islands', is just that; a string of six islands in the Florida Keys. Situated between the saltwater wilderness of Everglades National Park and the sapphire waters of the Florida Strait, Islamorada is truly an island paradise. It is located just ninety minutes south of Miami, and offers endless ways to explore and enjoy the crystal clear waters that surround this chain of islands. 

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Also known as the "Sportfishing Capital of the World", Islamorada is where backcountry sport fishing and saltwater fly fishing were pioneered. The unique topography of Islamorada creates thriving ecosystems for both marine and wildlife, offering exceptional snorkeling, diving, and interactive animal experiences.

Getting There & Around

The easiest way to get to the Keys is by car. The thin stretch of islands don't make much room for airstrips. Key Largo, the largest of the Keys, does have an airport, though with limited use. If you're coming from out of state, you can easily fly into Miami International Airport and rent a car. Islamorada is about an hour and a half drive south, depending on traffic.

Having a car in the Keys is a near necessity as many visitors 'Key hop' rather than stay in one location. The Keys are also part of the Uber network, and most islands have local taxi companies for those who don't want to drive.

Where to Stay

Islamorada has become a popular vacation home market for people throughout the world. From dream houses or seasonal homes, to rental properties or investment opportunities, our top choice for the best of the market is Ocean Sotheby's International Realty (OSIR). Their stellar team of realtors go above and beyond the typical call of duty. While they are backed by the world's top international, luxury real estate brand – Sotheby's International Realty, OSIR has the benefit of having a boutique real estate feel, perfectly suitable to the Islamorada lifestyle. With an array of gorgeous homes to rent or buy, the OSIR team is more than happy to get you settled quickly and seamlessly, so you can start living the island life in Islamorada.

 OSIR Glass House

OSIR Glass House

 OSIR Glass House

OSIR Glass House

 OSIR Glass House

OSIR Glass House

 OSIR Glass House

OSIR Glass House

The ease of working with the team at OSIR was just one of the reasons we chose a private home rental for our Islamorada vacation. "The Glass House” made for the perfect secluded getaway, and was the highlight of our trip. We were specifically looking for a location with more amenities than your typical hotel or resort. With a private beach, saltwater pool, fire pit, game room, full kitchen and grill, ample parking, wrap around balcony, hammocks galore, and floor-to-ceiling windows to watch the sun rise and set from every room, we really couldn't have asked for more. We thoroughly enjoyed morning dips in the oceanfront pool, breezy afternoons on the porch rockers, and lazy nights in the hammocks. Read all about our incredible weekend with OSIR here.

For information on this and other properties with OSIR, call 305-712-8888.

 Views from the Glass House

Views from the Glass House

 Glass House & Private Beach

Glass House & Private Beach

Some hotels we love in the area include:

1. The Moorings Village & Spa

The beachfront property that serves as both the backdrop and residence to the Rayburn house and resort is an actual place you can go and stay on vacation, but this isn't why it's our top resort choice. The Moorings is home to an 18-acre estate in Islamorada and is a virtual tropical oasis. It's tranquil nature and untouched beauty lends to the ideal, low key life most people are looking for on their Florida Keys vacation. Boasting more than 800 coconut palms and 18 private villas tucked into the lushly landscaped estate, you'll fall in love with this historic resort, which dates back to 1936!

2. Cheeca Lodge

Having undergone seven month of major renovations post Hurricane Irma, Cheeca Lodge offers more than just a caribbean style vacation. With partnerships or ownership at four local restaurants, dining options are a breeze. The hotel is also known for its iconic 525' wooden fishing pier, which has also been completely rebuilt. They also offer fishing charters and boat docking, host fishing tournaments, and have an array of waterspouts and aquatic activities to choose from.

3. Ocean House Resort

For an adults-only experience, Ocean House offers a private island oasis for travelers to the Florida Keys with beachfront massages, recreation, & warm weather. 

4. Casa Morada

For another adult-friendly resort (children over 16 years of age are welcome), Casa Morada is a great upscale option. With sixteen suites that are privately owned, the hotel offers a private, peaceful, and serene atmosphere. The highlight of the resort is Casa Morada's spectacular private island, which is accessed by a dramatic footbridge and features a fresh water pool, secluded cabana and the Sunset Gazebo bar with stunning views of the Gulf of Mexico.

What to Do
 Glass House Private Beach

Glass House Private Beach

 Picture Perfect Hammock at the Glass House

Picture Perfect Hammock at the Glass House

There is so much to do in Islamorada both day and night! The Keys are well known for being unique in offering spectacular sunrises and sunsets, so a beach walk at either time is an absolute must do. It's also home to an array of beautiful wildlife, like manatees, Florida Key Deer, coral reefs, tropical birds and fish, and so much more. The Atlantic Ocean and Florida Bay also offer parasailing, wind-surfing, paddle boarding, kayaking, and boat racing. For a more relaxing visit, enjoy a beachfront cocktail, sunset cruise, or explore the unique local shops and galleries.

 Boat Day with OSIR

Boat Day with OSIR

Fishing: Known as the Sport-Fishing Capital of the World, Islamorada is where saltwater fly fishing and backcountry sport fishing were pioneered, and offers the world’s highest density of professional offshore charter boats with tournament-grade captains. It’s unique location between Florida Bay (the “backcountry”) and the Atlantic Ocean (the “front side”), provides an unrivaled diversity of fishing opportunities. The Gulf Stream brings seasonal visitors like sailfish and marlin, kingfish and wahoo, dolphin (mahi-mahi) and tuna close enough to shore to be targeted by small-boat anglers, while tarpon and bonefish are among inshore species coveted by light tackle anglers. 

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Snorkeling: The Florida Keys are well known for their beautiful shallow coral reefs, and Islamorada snorkeling is some of the best in the Keys. The reefs range in depths from four to twenty feet, which makes snorkeling a breeze. Whether you are a beginner or an advanced snorkeler, you will definitely enjoy the spectacular scenery below. Tropical fish congregate by the thousands amidst colorful coral heads, sea rays, and fauna in the crystal clear sapphire and emerald waters of Islamorada. Bring your underwater camera and capture the vast underwater sea life and spectacular views.

 Boat Day with OSIR

Boat Day with OSIR

Boat Charters: Islamorada offers several exhilarating sightseeing charters including eco-tours, snorkeling, historic island tours, Everglades tours, sunset cruises and more. Private charters can be customized to explore the emerald seas surrounding the Keys. Delve into the serene coral reefs and vibrant marine life surrounding local landmarks including Indian Key, Lignumvitae Key, Alligator Reef Lighthouse, Cheeca Reef, and Everglades National Park. Or opt for a unique bar hopping boat cruise to tour the local waterfront watering holes.

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Robbie's Marina: Home of the world renowned tarpon feeding, Robbie's offers a unique opportunity to hand feed massive tarpon, surrounded by friendly pelican. Enjoy their famous loaded Trailer Trash Bloody Mary on the waterfront deck overlooking the tarp feeding frenzy. Then stroll through their outdoor market, featuring local artists, shops, and handcrafted souvenir. Robbie's Marina also offers a variety of waterspout activities on property. 

 {Photo: Theater of the Seas}

{Photo: Theater of the Seas}

Theater of the Sea: Family owned and operated since 1946, Theater of the Sea is one of the oldest marine mammal facilities in the world. Their lagoons and lush, tropical gardens are home to Atlantic bottlenose dolphins, California sea lions, sea turtles, tropical and game fish, sharks, stingrays, alligators, marine invertebrates, and birds. Interactive programs include daily dolphin and sea lion shows, fish and reptile tours, bottomless boat rides, sea turtle and alligator encounters, and most impressively, swimming with dolphins, sea lions, rays, and sharks! Their 30 minute dolphin swims include trained behaviors (like dorsal tows, kisses, and hugs) as well as swimming and snorkeling with dolphins. This is guaranteed to be an experience of a lifetime.

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Florida Keys Brewing Company: Florida Keys Brewing Company is the Upper Keys first microbrewery, located in the Morada Way Arts and Cultural District. This whimsical and psychedelic spot offers a great selection of favorite beers, as well as a rotating list of seasonal and barrel aged beers. Enjoy a flight of beers in their picturesque beer garden, sprawled with bougainvillea, vibrant lawn furniture, and garden games, including life-size jenga. The brewery also offers tours and tastings of their staple brews, including Iguana Bait, a honey hibiscus kolsch made with local Keys honey and hibiscus.

Where to Eat
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Ziggie and Mad Dog's: Keys elegance at it's finest, this upscale stalwart is known for its steaks, chops & local seafood, and is an Islamorada fine-dining staple. Refined dishes and exceptional service in a rustic setting, Ziggie and Mad Dog's has perfected their world class cuisine and extensive cocktail list. Try the Delmonico Ribeye or fresh catch of the day Oscar style, accompanied by the truffle lobster mac n' cheese and pistachio creamed spinach to share (or not). Absolute perfection.

Cafe Moka: Don't be fooled by this quaint breezy island cafe, Cafe Moka serves up the freshest flakey pastries alongside fresh brewed espresso, making it the ideal spot to start (or end) your day. The French homemade pastries are absolutely heavenly. We recommend the salmon and cream cheese croissant and gooey melted cheese bread. They also make drool-worthy sandwiches and flatbreads like Prosciutto Brie and Goat Cheese and Honey. Yes please!

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Morada Bay: Come by car or boat to this beachfront dining experience serving up Caribbean-style American eats and views for days. Settled on the pristine white sand beach, the picturesque restaurant boasts vibrant Keys colors alongside the Turquoise ocean water. A seafood focused menu offers fresh dishes, including Tuna Tataki, Conch Salad, and Cashew Crusted Salmon. Be sure to save room for dessert, because Fried Oreos with Amaretto Cream Dipping Sauce!

Kaiyo Grill & Sushi: Kaiyo Grill & Sushi is Islamorada’s first Asian fusion and sushi restaurant, and one of the Florida Key’s preeminent culinary experiences. Beckoning locals and travelers alike, Kaiyo Grill & Sushi is lauded for the freshest sushi in the Keys, featuring Yellowfin Tuna, Sea Urchin, and classic Thai Green Curry. Their diverse menu rivals any big city eatery. We recommend the Islamorada Roll and Tuna Squared with a bottle of sake for the table. Feeling adventurous? Try their dessert sushi for a whimsical sweet treat.

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Green Turtle Inn Restaurant: A local favorite for seafood inspired dishes couples modern fare with an authentic Keys-casual vibe. An Islamorada institute since 1947, The Green Turtle Inn serves up some of the best bites in the Keys. Innovative brunch specials include Snapper and Eggs, Tilefish Omelet, Crabcake Benedicts, and their infamous "Bacon Wrapped Love". Also featured on "Diners, Drive-Ins and Dives", this is a Florida Keys must-try spot. Tip: come early on the weekends, as the wait can be as hefty as their portions!

 

Whether you're an adventure junkie or just need some rest and relaxation, this island oasis offers something for everyone. Postcard perfect scenery, vast array of activities, and fresh seafood on every corner, you are guaranteed to live island life to it's fullest in lovely Islamorada. To read more about our incredible weekend in the Florida Keys, click here!