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Nestled by the waves, this chill oceanfront resort features nautical rooms, lush gardens, tons of dining options, and a lively poolside vibe.

Ziggie & Mad Dog’s is a lively steakhouse in Islamorada, celebrated for its fresh seafood, prime cuts, and a chill vibe that keeps them buzzing every night.

Nestled in polished island-style vibes, this upscale seafood spot offers fresh fish and New American delights, perfect for date nights or brunches.

A lively marina hotspot in the Keys, featuring tarpon feeding, kayak rentals, and a fun restaurant that serves up delicious eats and drinks.

Nestled on a lush 18-acre former coconut plantation, this tranquil beachfront resort boasts serene cottages, a heated pool, and attentive service amidst tropical beauty.

Tropical oceanfront resort with a private beach & heated pool, plus a rum bar and a restaurant. This upscale oceanfront resort is 2 miles from Indian Key Historic State Park, and 5 miles from aquatic shows at the Theater of the Sea marine park. The chic, island-themed rooms feature Wi-Fi, flat-screen TVs and coffeemakers; many have balconies with ocean views. Suites add sitting areas and kitchenettes. There's an Italian restaurant, and a poolside rum bar serves lunch and dinner. The private beach has hammocks and loungers, and the heated outdoor pool overlooks the ocean. A resort fee covers Wi-Fi, parking and a shuttle service.

Nestled on Florida Bay, this tranquil Caribbean-inspired gem boasts spacious suites, a private island, and endless outdoor fun, making it an ideal retreat.

Nestled in the heart of Islamorada, Florida Keys Brewing offers a vibrant beer garden, live music, and delicious tacos, making it the ultimate chill spot in the Keys.

Flaunting ocean views and a casual vibe, Oceanside Safari Restaurant offers a fresh menu, warm service, and a charming atmosphere perfect for a Keys getaway.

Nestled on the beach, this romantic Colonial-style gem serves up exquisite world cuisine with stunning sunset views, perfect for any special occasion.