WELCOME TO ISLAMORADA

Nestled in the heart of the Upper Florida Keys, The Village of Islands stretches gracefully between Mile Markers 90 and 72 — just one hour south of Miami. This exclusive enclave offers an impressive collection of refined vacation homes and private retreats, perfectly positioned for those seeking the ultimate Keys escape.

Comprising four breathtaking islands spanning 18 miles, Islamorada encompasses approximately 3,900 acres of pristine land and turquoise waters. Revered as the Sport Fishing Capital of the World, this prestigious destination attracts discerning travelers and serious anglers alike.

Here, world-class game fishing awaits — from the tranquil backcountry waters of the Gulf of Mexico to the legendary deep blue seas just beyond the powerful currents of the Gulf Stream. This fast-moving natural channel runs closer to shore in the Upper Keys, offering unparalleled access to some of the finest sport fishing and sailing experiences found anywhere in the world.

THE NEIGHBORS

Vacationers, elite second-home owners and year-round residents with an obsession for the sea

Islamorada is a cherished destination for vacationers, discerning second-home owners, and year-round residents who share a deep passion for the sea.

With a permanent population of just over 6,600, this exclusive island village exudes timeless charm and refined elegance. Soft pastel-colored buildings, graceful palm trees, and vibrant cascades of pink bougainvillea create an atmosphere of effortless sophistication and natural beauty.

By charter, the Village of Islamorada extends from the western end of the Channel Two Bridge (near Mile Marker 72.5) to the western end of the Tavernier Creek Bridge (near Mile Marker 90.8). This prestigious enclave encompasses the islands of Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key, and Tea Table Key — all gracefully connected by the iconic Overseas Highway.

WHAT TO EXPECT

Serious water enthusiasts with boats of all sizes and shapes

Bathed in endless sunshine, Islamorada offers a sophisticated blend of exhilarating water sports in crystal-clear turquoise waters, charming locally-owned restaurants, elegant shops, distinguished art galleries, and boutique micro-breweries scattered throughout the island.

Dining reaches new heights with exquisite establishments such as Chef Michael’s, Ziggie & Mad Dogs, Kaiyo Grill & Sushi Bar, and the acclaimed Pierre’s. Whale Harbor Restaurant remains a perennial favorite, renowned for its legendary all-you-can-eat seafood buffet and expansive outdoor rooftop bar overlooking the ocean and the lively boat-filled sandbar. Live entertainment gracefully echoes across the island chain from day into night.

The iconic Islamorada Sandbar, one of the most celebrated in the Florida Keys, lies just offshore in front of the stylish Postcard Inn, formerly the legendary Holiday Isle Resort. During the summer months, an impressive array of yachts and fine vessels gather in the pristine shallow waters along the edge of the Whale Harbor Channel, creating an exclusive and vibrant waterside scene.

Islamorada is blessed with abundant community parks and lush green spaces. At the heart of the island chain sits Founders Park at Mile Marker 87 — a premier bayside sanctuary where families enjoy ball fields, a modern aquatic center, and a serene sandy beach. The village also proudly owns Plantation Yacht Harbor Marina, offering 83 wet slips along with fuel and pump-out services for discerning boaters.

THE LIFESTYLE

A carefree attitude in a idyllic setting removed from the hustle and bustle of life

Islamorada is an enchanting island village adorned with pristine offshore sandbars, charming pastel-colored outdoor cafés, a celebrated foodie scene, and vibrant live entertainment that flows from day into night.

The village calendar shines with prestigious annual events, including world-class fishing tournaments, the acclaimed Uncorked Islamorada Food & Wine Festival, the Annual Nautical Expo, the monthly Third Thursday Art Walk in the Morada Way Arts and Cultural District near Cheeca Lodge, Outdoor Pops in the Park, Art Under the Oaks, Saltwater Sportsman National Fishing Seminars, and the elegant Full Moon Parties at the sophisticated Morada Bay Beach Café.

Notably, the critically acclaimed three-season Netflix thriller series Bloodline was filmed on location in Islamorada at the exclusive Moorings Village and the picturesque Morada Bay.

UNEXPECTED APPEAL

The azure colors of the water everywhere and number of connecting island bridges

Photographers from around the world are drawn to Islamorada to capture its breathtaking natural beauty and unparalleled scenic splendor.

The environment of the Florida Keys is unlike anywhere else in the United States. Encompassing over 2,900 square nautical miles, the Florida Keys National Marine Sanctuary stands as a pristine sanctuary, protecting some of the most magnificent coastal waters in the world. Here, visitors discover thriving underwater coral reef restoration farms, graceful connecting bridges arching over sparkling aquamarine waterways, and elegant marinas filled with luxurious yachts and high-end sportfishing vessels.

It is in Islamorada that America’s most iconic and beautiful scenic drive — the legendary journey south to Key West — truly begins.

THE MARKET

A varied mix of oceanfront condominiums, two-and-three story stilt homes and oceanfront estates

Islamorada unfolds across three distinguished enclaves — Upper Matecumbe, Lower Matecumbe, and Plantation Key — comprising approximately 5,700 residences within this coveted archipelago sanctuary.

The real estate landscape here is as varied as it is extraordinary. Entry-level dry lot estates begin in the $700s, while deepwater canal properties command prices from $1.4 million — each offering effortless access to some of the world's most prized sportfishing and sailing waters. Oceanfront homes with private boat dockage are presented from $3.5 million, and for the most discerning buyer, the crown jewels of Islamorada's legendary Millionaires' Row — sweeping oceanfront estates of unrivaled grandeur — are offered at prices exceeding $42 million.

For those seeking a foothold in this exclusive enclave as an income-producing asset, Islamorada maintains a refined 28-day minimum vacation rental policy, preserving the community's distinguished character. A select portfolio of legacy properties, however, holds coveted 7-day rental licenses grandfathered prior to the policy change — a rare and increasingly valuable distinction.

YOU’LL FALL IN LOVE WITH

Pastel-colored cottages, decadent resorts, curvy palm trees and fiery sunsets

From the first light of morning, an irresistible energy stirs — a quiet urgency to embrace every golden moment this paradise has to offer. Gentle Atlantic breezes drift through swaying palms and weathered tiki huts, carrying with them the unhurried rhythm of island life at its most refined.

Lush tropical foliage cascades in every direction, alive with the flutter of exotic birdlife and punctuated by brilliant bursts of fuchsia bougainvillea — nature's own masterpiece, painted fresh each day. Here, beauty is not an amenity; it is simply the landscape.

Islamorada possesses a rare and undeniable magnetism — the kind that quietly rewrites your definition of home, and makes the thought of leaving feel, quite simply, unimaginable.