Where to Stay in the Florida Keys: Key Largo vs. Islamorada vs. Marathon vs. Key West

Dreaming of a Florida Keys getaway but not sure where to stay? The island chain offers distinct experiences depending on which part you choose—from laid-back nature adventures to lively nightlife and everything in between. If you're torn between Key Largo, Islamorada, Marathon, or Key West, here’s a breakdown of what makes each Key unique—and why staying in the Middle Keys might just be the best of all worlds.

Key Largo: The Diving Capital of the World

Located at the top of the Florida Keys, Key Largo is the first island you’ll hit when driving from Miami. It’s best known for its incredible underwater experiences. John Pennekamp Coral Reef State Park is a must-visit for snorkeling, diving, and glass-bottom boat tours. It’s also a haven for eco-tourism with plenty of mangroves, kayak trails, and marine sanctuaries.

• Best for: Scuba diving, snorkeling, and nature-focused travelers

• Vibe: Relaxed, eco-conscious, and a little rustic

Islamorada: The Fishing Capital of the World

Just south of Key Largo lies Islamorada, often called the “Sportfishing Capital of the World.” With offshore fishing charters, the Islamorada Sandbar, and Alligator Reef, it’s the perfect playground for anglers, boaters, and snorkelers. Islamorada also offers upscale dining, art galleries, and a growing craft beer scene, blending adventure with a touch of luxury.

• Best for: Fishing, boating, boutique dining

• Vibe: Upscale island charm with a sporty twist

Marathon: The Heart of the Keys

Sitting right in the middle of the Florida Keys, Marathon offers a balance of natural beauty, family-friendly attractions, and easy access to both the Upper and Lower Keys, perfect for day trips. It’s home to Sombrero Beach, Crane Point Hammock, and the Turtle Hospital, making it ideal for those who want a relaxing vacation with access to outdoor activities.

• Best for: Families, boaters, and travelers seeking a central location

• Vibe: Quiet, low-key, and community-oriented

Key West: Culture, Nightlife, and Historic Charm

At the southernmost tip of the Keys, Key West offers an entirely different flavor. Known for its sunset celebrations at Mallory Square, Duval Street nightlife, and historical landmarks like Ernest Hemingway’s House and Fort Zachary Taylor, it’s a lively town full of color and character.

• Best for: Nightlife, history, LGBTQ+ travelers, and culture lovers

• Vibe: Eclectic, energetic, and a bit quirky—in the best way

Why the Middle Keys is the Best Home Base

If you want to explore all that the Florida Keys have to offer without committing to just one vibe, staying in the Middle Keys gives you the perfect jumping-off point. Grassy Flats Resort & Beach Club, located in Marathon, puts you within easy reach of everything—from the reefs of Key Largo to the sunset parties of Key West—all while offering a peaceful retreat to recharge.

You can spend the morning snorkeling off Islamorada, the afternoon beachcombing in Key West, and be back in time for sunset cocktails at the resort. Plus, staying mid-Keys cuts down on long drives and lets you spend more time doing what you came for—relaxing, exploring, and making memories.

Each island in the Florida Keys has its own personality. Whether you’re chasing coral reefs in Key Largo, casting a line in Islamorada, soaking up the sun in Marathon, or dancing the night away in Key West, there’s no wrong choice—only the right starting point.