Places to Stay

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

Discover unforgettable Florida Keys vacations with cozy condos to oceanfront estates!

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.

Looe Key Reef Resort offers beachfront accommodations, daily scuba and snorkeling trips, a full-service dive shop, and a Tiki Bar with live entertainment in the Florida Keys.

Florida Keys' largest oceanfront RV site, book now.

Pier House Resort & Spa is a historic oceanfront retreat in Old Town Key West, featuring a private white sand beach, full-service spa, three dining venues, and the iconic Chart Room Bar

Southwinds Motel is a budget-friendly, adults-only hotel in Old Town Key West, offering two outdoor pools, complimentary continental breakfast, and convenient access to Duval Street and the Atlantic Ocean.

Island City House Hotel blends historic charm with lush gardens, pool, and three unique guesthouse styles in Old Town Key West. Perfect for families, wedding groups, or history lovers.

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.

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

Charming Key West oasis with private baths, heated pool, and prime location.

Rainbow Bend Resort is a family-friendly, oceanfront retreat in Marathon, Florida, offering a private beach, saltwater pool, and hot tub with ocean views.

Casa Marina Key West is a historic oceanfront resort featuring elegant accommodations, beachfront amenities, and classic island charm.