Places to Stay

Historic charm meets vibrant Key West life steps from Hemingway House and the iconic lighthouse.

Hawks Cay Resort is a luxury resort on Duck Key offering five pools, a saltwater lagoon, a full-service marina, and a spa.

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.

The Banyan Resort is a charming, historic all-suite resort nestled in the heart of Old Town Key West

Luxury waterfront vacation rentals in Marathon & Key Colony Beach, FL. Private pools, docks, and dog-friendly accommodations. Sleeps 8–10.

Dolphin Vacations offers a curated selection of vacation rentals in Key West and Marathon, FL, including historic homes and modern condos. Properties like Casa Rosa provide private pools and prime locations near Duval Street.

Breezy Palms Resort offers a family-friendly, oceanfront experience with accommodations including poolside apartments, two-bedroom units, beach cottages, oceanfront apartments, and bungalows.

Key Largo Inn offers budget-friendly, Caribbean-style accommodations with a pool, full bar, and dive shop, centrally located in Key Largo.

H2O Suites is an adults-only luxury hotel in Key West, offering 22 contemporary suites with private plunge pools, Italian marble bathrooms, and rooftop pool access, just steps from Duval Street.

Private tropical paradise on Key West’s quiet Atlantic side with charming beachside suites.

Southernmost Beach Resort & Guesthouses is an oceanfront Key West escape featuring multiple heated pools, beachfront dining, a full-service spa, and lush tropical gardens just steps from Duval Street.

Charming boutique hotel in historic Key West with spacious rooms and pool.

Conch Key Cottages offers charming waterfront accommodations on Conch Key in the Florida Keys. Guests can enjoy private cottages with boat slips, ideal for fishing and exploring nearby attractions.

Florida Keys Brewing Co. is the Upper Keys’ first microbrewery, serving award-winning craft beers in a vibrant beer garden and taproom located in Islamorada’s Morada Way Arts District—perfect for beer lovers and locals alike. Also offers a vacation rental.

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.