Places to Stay

Escape to paradise at Chesapeake Beach Resort—luxury oceanfront stays in the Florida Keys.

The Speakeasy Inn is a historic adults-only guesthouse in Old Town Key West, offering tropical-themed suites, a wraparound porch, and a Rum Bar featuring over 350 rums.

Wicker Guesthouse is a charming, adults-only boutique inn in the heart of Old Town Key West.

Discover a curated selection of vacation homes in Marathon, FL, featuring private pools, docks, and waterfront views. Ideal for families and groups seeking a relaxing Keys getaway.

Island Bay Resort is an adults-only boutique escape with tropical cottages, a private beach, and free kayaks & SUPs.

Monte Christo Condominiums is a luxury oceanfront retreat in Key Colony Beach, offering two- and three-bedroom condos with resort-style amenities.

The Laureate Key West is a luxury all-suite hotel offering serene bayfront views, coastal chic decor, and modern amenities.

Charming Old Town Key West villas and B&B suites with pool.

Barefeet Vacation Rentals — premium vacation homes and condos in the Upper Florida Keys, all along Key Largo’s scenic Overseas Highway.

Sunset Key Cottages is a luxury resort situated on a 27-acre private island just 500 yards off Key West, offering upscale one- to four-bedroom cottages with wraparound verandas and panoramic ocean views.

Eco-friendly boutique resort in the Florida Keys with oceanfront dining, water sports, and unique "olde Florida" charm.

The Saint Hotel Key West, Autograph Collection, is an adults-only boutique hotel located at 417 Eaton Street in Old Town Key West.

Key West villas steps from Duval Street, private pool, pet-friendly.

Margaritaville Beach House Key West offers laid-back, island-inspired accommodations steps from Smathers Beach, with a lagoon-style pool and on-site bar & grill.

Heron House Hotels offers two charming, adults-only properties—Heron House and Heron House Court—featuring lush gardens, an outdoor pool, rooftop sundeck, and complimentary continental breakfast.