Discover the beauty and allure of Islamorada’s legendary beach and fishing destination – the Chesapeake Beach Resort. Lose yourself amidst swaying palm trees, endless ocean vistas, flowering hibiscus, exotic birds, and a lush private lagoon. A 6.5-acre oceanfront property, our Islamorada hotel offers a tranquil sanctuary of sparkling white sands and tropical gardens— the perfect island getaway. Select one of... Read More about Chesapeake Beach Resort

Welcome to our boutique oasis. Our property consists of two guest houses and 16 suites . Our nightly rates include complimentary breakfast, complimentary use of our kayaks, paddle boards, and bicycles as well as complimentary yoga every Wednesday, Saturday and Sunday.

Cozy, comfortable, clean, and convenient, Creekside Inn is the ideal spot to stay for your Florida Keys adventure. Our charming hotel is the perfect base for enjoying the best of the area, including unbeatable water sports, full-service marinas, and spectacular views. Whether you’re docking your boat on property and enjoying some of the world’s best fishing, or stopping through as... Read More about Creekside Inn Islamorada

Welcome to The Caribbean Resort of Islamorada, Florida, home to some of the best fishing and diving in the Florida Keys. Nestled in the heart of the fishing capital of the world, The Caribbean Resort of Islamorada, Florida, has won the hearts of many. While the panoramic ocean views, inviting Caribbean-style homes, endless fishing pier and beach-entry pool keep guests... Read More about The Caribbean Resort

Welcome to Ocean Gardens Islamorada Florida. This unique nautical gallery & boutique feels more like a local attraction than a store. Guests spend hours searching for their perfect treasure here on the site or at the store. Search for Marine antiques including English Channel buoy lights, treasure coins from the 1733 Spanish treasure fleet, shells, coral and one-of-a-kind nautical home... Read More about Ocean Gardens

La Siesta Resort & Villas offers a variety of places to stay, from rooms and suites to beachfront cottages and entire vacation homes for rent. Our Florida Keys resort includes accommodations with charming garden and sweeping ocean views—some are even located right on the beach! Take a look and choose which one is right for you.

Bayside Villas by Islander Resort is your home away from home in the Florida Keys. Our townhome-style beachfront accommodations are the ideal stay for group getaways, family vacations, and extended stays in beautiful Islamorada. Plus, our exceptional on-site amenities including boat slips and bay view pool, ensure that our experiences are second-to-none. We may be nestled in of the world’s... Read More about Islander Bayside Villas

Welcome to a one-of-a-kind place of possibilities. Fifteen waterfront acres of invigorating adventure and idyllic relaxation in the heart of the Florida Keys. A family-friendly place of easygoing enjoyment and simple pleasures, with a variety of bright, island-inspired guestrooms and cottages. And The Cove, an adult-centric resort-within-a-resort, features a tranquil, private beach lagoon.

Nestled in the heart of Islamorada, FL, La Jolla Resort offers the perfect blend of relaxation and luxury for your next getaway. As a premier resort in this tropical paradise, we provide a serene escape for guests looking to unwind and indulge in the beauty of the Florida Keys. Our resort embodies the essence of seaside living with stunning ocean... Read More about La Jolla Resort