Places to Stay

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.

Pines & Palms Resort — a boutique, ocean-front retreat in Islamorada offering a peaceful Keys-style village with cottages and suites.

Luxury Florida Keys vacation rentals with private pools, beach access, and endless ocean adventures await!

Key Lime Sailing Club & Cottages offers a unique, all-inclusive waterfront retreat in Key Largo, featuring self-contained cottages with unlimited sailboat use, kayaks, snorkeling gear, and more.

Explore KeysCaribbean: Expert hotel management and luxury vacation rentals.

Bud N' Mary's: Florida Keys' oldest, largest fishing fleet with charters, lodging, and epic fishing adventures!

Tarpon Flats Inn & Marina is a boutique waterfront retreat in Key Largo, offering five spacious, air-conditioned rooms with kitchenettes, private beach access, and complimentary kayaks for exploring the surrounding waters.

Discover a historic Key West icon blending vintage flair with modern luxury.

Tropical Inn is an intimate, adults-only boutique inn located on historic Duval Street in Key West.

Scuba Town USA in Islamorada offers an all-in-one dive and vacation experience with lodging, dining, pools, a private beach, and access to multiple dive-related businesses, all set within Three Waters Resort & Marina.

The Garden House is a charming bed & breakfast nestled in Old Town Key West, offering cozy accommodations, a tranquil garden pool, and personalized concierge services—all just steps from Duval Street.

Luxurious Key West all-suite retreat with kitchens, pools, and Duval vibes.

Freewheeler Vacations is the Upper and Middle Keys’ largest and longest-running vacation rental company, offering everything from cozy condos to grand estates, backed by 30+ years of expert service.