Square Grouper Bar & Grill
22658 Overseas Hwy, Cudjoe Key, FL 33042

Discover the best restaurants in Cudjoe Key and the Lower Florida Keys, where fresh seafood, island-inspired cuisine, and laid-back waterfront dining define the local experience. Whether you’re looking for a casual breakfast café, authentic Cuban flavors, a sunset tiki bar, or a chef-driven dinner spot, Cudjoe Key offers easy access to some of the most beloved eateries between Marathon and Key West. This curated dining guide highlights top-rated restaurants near Cudjoe Key, making it easy to explore local favorites, hidden gems, and must-visit spots just minutes from your stay.
Visitors staying in Cudjoe Key are perfectly positioned to explore some of the most iconic dining spots in Key West and Stock Island, all within an easy drive down the Overseas Highway. From fresh-caught seafood and waterfront happy hours to Cuban comfort food, tapas, and legendary island brunch, this curated guide highlights standout restaurants near Cudjoe Key, complete with addresses, click-to-call phone numbers, and directions to help you plan the perfect Keys meal.
Seafood • American • Waterfront
22658 Overseas Hwy, Cudjoe Key, FL 33042
Cocktails • Lounge • Late Night
22658 Overseas Hwy (Upstairs), Cudjoe Key, FL 33042
Seafood • American • Patio
22642 Overseas Hwy, Cudjoe Key, FL 33042
Breakfast • Coffee • Brunch
22960 Overseas Hwy, Cudjoe Key, FL 33042
Cuban • Latin • Cafe
22960 Overseas Hwy, Cudjoe Key, FL 33042
Steak • Seafood • Wood-Fired
22952 Overseas Hwy, Cudjoe Key, FL 33042
Seafood • Island Fare • Tiki
22604 Overseas Hwy, Summerland Key, FL 33042
American • Grill • Casual
24381 Overseas Hwy, Summerland Key, FL 33042
American • Bar • Family-Friendly
27205 Overseas Hwy, Ramrod Key, FL 33042
Tiki Bar • Seafood • Casual
27340 Overseas Hwy, Ramrod Key, FL 33042
Sandwiches • Cuban • Quick Bite
27009 Overseas Hwy, Ramrod Key, FL 33042
Seafood • Waterfront • Live Music
183 Barry Ave, Little Torch Key, FL 33042
Pizza • Burgers • Iconic Keys Pub
30813 Watson Blvd, Big Pine Key, FL 33043
Deli • Grab & Go • Convenience
22940 Overseas Hwy, Cudjoe Key, FL 33042
Pizza • Casual • Takeout
22960 Overseas Hwy, Cudjoe Key, FL 33042
Tacos • Mexican-Inspired • Quick Bite
24437 Overseas Hwy, Summerland Key, FL 33042
Coffee • Breakfast • Sandwiches
1211 Simonton St, Key West, FL 33040
Seafood • Food Truck • Local Favorite
Rotating Location, Key West, FL
Staying in Cudjoe Key? These Key West and Stock Island favorites are an easy drive for brunch, sunset dining, fresh seafood, Cuban classics, tapas, and iconic island vibes.
Brunch • Caribbean • Iconic Key West
729 Thomas St, Key West, FL 33040
Oceanfront • Upscale • Sunset Dining
700 Waddell Ave, Key West, FL 33040
Seafood • Raw Bar • Harborfront
700 Front St, Key West, FL 33040
Seafood • Fine Dining • Key West Bight
700 Front St, Key West, FL 33040
Cuban • Local Favorite • Comfort Food
900 Catherine St, Key West, FL 33040
Breakfast • Steaks • Historic Key West
806 Caroline St, Key West, FL 33040
Caribbean • Island Fusion • Duval St
628 Duval St, Key West, FL 33040
Street Eats • Tacos • Late Night
409 Caroline St, Key West, FL 33040
Oysters • Seafood • Happy Hour
231 Margaret St, Key West, FL 33040
Oceanfront • Casual • Wood-Fired
1400 Duval St, Key West, FL 33040
Lunch • Cocktails • Lively Atmosphere
951 Caroline St, Key West, FL 33040
Waterfront • Seafood • Local Hangout
6810 Front St, Stock Island, FL 33040
Pizza • Italian • Easy Drive
5620 MacDonald Ave, Key West, FL 33040