Places to Stay

The Mansion on the Sea (Southernmost House) is an adults-only historic boutique hotel in Key West offering oceanfront rooms, a heated infinity pool, and complimentary breakfast.

Simonton Court Historic Inn & Cottages is a tranquil adults-only boutique inn in Old Town Key West, offering four outdoor pools, daily continental breakfast, bike rentals, and lush tropical gardens just steps from Duval Street.

Fitch Lodge: Your cozy, bohemian Key West basecamp steps from the Historic Seaport.

Courtyard by Marriott Key Largo — comfortable Key Largo hotel with full-service marina, pool, fitness center and easy access to Florida Keys adventures.

Caribbean House is a charming Bed & Breakfast located in historic Bahama Village, just two blocks from Duval Street.

Hadley House Resort is a laid-back waterfront hotel in Islamorada, offering rooms with kitchenettes, a private beach, an outdoor pool, and complimentary breakfast, all just steps from the Atlantic Ocean.

RentalsInMarathon.com offers stunning vacation homes in the heart of the Florida Keys. Experience breathtaking ocean views, pristine beaches, and vibrant marine life. Perfect for relaxation and adventure, their handpicked rentals provide comfort and...

Ocean Key Resort & Spa in Key West offers luxury accommodations with Gulf views, a rooftop pool, three waterfront dining options, and a full-service spa, all located at the iconic Zero Duval Street.

Casa 325 is a charming boutique guesthouse in the heart of Key West’s Historic Old Town. Tucked just off lively Duval Street, it offers uniquely designed rooms, a pool, and easy access to shops, dining, and attractions.

Experience resort-style fun with the largest pool in the Florida Keys, ocean-view lounging, a speakeasy game room, marina access, and exclusive tennis and pickleball courts—including the Keys’ only indoor pickleball court.

The Southernmost Inn is an adults-only boutique hotel in Old Town Key West.

Cuban vibes meet Key West charm—discover Havana Cabana.Havana Cabana at Key West is a Cuban-inspired hotel featuring the largest pool in Key West, a poolside bar, and a food truck serving Cuban cuisine.