TOP 30 Best Romantic dining in Islamorada, Florida

Square Grouper Islamorada is a charming waterfront restaurant located at 80460 Overseas Highway in Islamorada, Florida. This popular eatery offers a laid-back atmosphere with stunning views of the ocean, making it the perfect spot for a relaxing meal. The menu features a variety of fresh seafood dishes, as well as other delicious options to satisfy any craving. Whether you're looking for a casual lunch or a romantic dinner, Square Grouper Islamorada is sure to impress with its welcoming ambiance and mouthwatering cuisine.

Habanos Oceanfront Dining is a low-key Cuban restaurant located at 73510 Overseas Highway in Islamorada, Florida. This casual beachfront eatery offers classic Cuban dishes such as ham, pork, and Swiss cheese sandwiches on sweet buns, as well as thin-sliced steak sandwiches on Cuban bread with lettuce, tomato, and potato sticks. Their menu also features a variety of pizzas topped with ham, pepperoni, chorizo, bacon, and more. Customers can customize their pizzas with additional toppings for an extra charge. Please note that consuming raw or undercooked meats, poultry, seafood, shellfish, or eggs may increase the risk of foodborne illness. Enjoy a taste of Cuba at Habanos Oceanfront Dining!

Sands of Islamorada Hotel & Resort is a luxurious lodging destination located at 80051 Overseas Highway in Islamorada, Florida. Offering a perfect blend of tropical charm and modern amenities, this resort is the ideal retreat for those seeking a relaxing getaway in the beautiful Florida Keys. Guests can enjoy stunning ocean views, pristine beaches, and top-notch service during their stay. Whether you're looking to relax by the pool, explore the nearby attractions, or indulge in delicious dining options, Sands of Islamorada Hotel & Resort has everything you need for a memorable vacation experience.

Creekside Inn Islamorada is a charming lodging establishment located along the picturesque Old Highway in Islamorada, Florida. Surrounded by lush tropical gardens and just a stone's throw away from the crystal-clear waters of the Florida Keys, this inn offers a tranquil and relaxing retreat for guests looking to escape the hustle and bustle of everyday life. The cozy rooms are tastefully decorated and equipped with modern amenities to ensure a comfortable stay. Guests can enjoy a refreshing dip in the outdoor pool, relax in the hot tub, or take a leisurely stroll along the nearby creek. With its convenient location and laid-back atmosphere, Creekside Inn Islamorada is the perfect choice for a memorable vacation in the Florida Keys.

Sunset Lounge is a cozy and inviting restaurant located at 80460 Overseas Highway in Islamorada, Florida. With stunning views of the sunset over the water, this establishment offers a relaxed atmosphere where guests can enjoy delicious food and drinks. Whether you're looking for a romantic dinner for two or a casual meal with friends, Sunset Lounge is the perfect spot to unwind and savor the flavors of the Florida Keys. Come experience the laid-back charm and mouthwatering cuisine that make Sunset Lounge a must-visit destination in Islamorada.

The Caribbean Resort, located at 117 Carroll Street in Islamorada, Florida, is a charming lodging option that offers a taste of the Caribbean right in the heart of the United States. With its tropical-inspired decor, lush gardens, and stunning ocean views, this resort is the perfect escape for those looking to relax and unwind in a beautiful setting. Whether you're lounging by the pool, enjoying a cocktail at the beachside bar, or exploring the nearby attractions, The Caribbean Resort provides a tranquil and luxurious retreat for guests seeking a slice of paradise.

SHIMA is a charming restaurant located at 88005 Overseas Highway in Islamorada, Florida. Known for its delectable food and inviting atmosphere, SHIMA offers a unique dining experience that combines traditional Japanese cuisine with a touch of local flair. Guests can enjoy a wide variety of fresh sushi, sashimi, and other Japanese dishes made with the finest ingredients. Whether you're looking for a romantic dinner for two or a fun night out with friends, SHIMA is the perfect place to indulge in delicious food and create lasting memories.

The Moorings Village is a charming lodging institution located at 123 Beach Road in Islamorada, Florida, United States. Nestled in a picturesque seaside setting, this luxurious retreat offers guests a tranquil and rejuvenating escape from the hustle and bustle of everyday life. With its beautifully appointed accommodations, lush tropical gardens, and pristine white sandy beaches, The Moorings Village provides the perfect backdrop for a relaxing vacation or romantic getaway. Whether you are seeking a peaceful retreat or an adventurous beach vacation, The Moorings Village offers a unique and unforgettable experience for all who visit.

Tides Beachside Bar & Grill is a charming waterfront restaurant located in Islamorada, Florida. Situated at 82100 Overseas Highway, this establishment offers a relaxed and casual dining experience with stunning views of the ocean. Guests can enjoy a delicious menu featuring fresh seafood, grilled meats, and refreshing cocktails. Whether you're looking for a romantic dinner by the water or a fun lunch with friends, Tides Beachside Bar & Grill is the perfect spot to unwind and savor the flavors of Florida.

Islander Resort is a luxurious lodging facility located at 82100 Overseas Highway in the beautiful town of Islamorada, Florida. Situated in the heart of the Florida Keys, this resort offers guests a serene and picturesque retreat with stunning ocean views and pristine beaches. The resort features spacious and well-appointed rooms, a range of amenities including a pool, spa, and on-site dining options. Perfect for a romantic getaway, family vacation, or corporate retreat, Islander Resort provides a peaceful and relaxing atmosphere for guests to unwind and enjoy the tropical paradise of the Florida Keys.

Oceanside Safari Restaurant & Lounge is a vibrant and lively establishment located at 73814 Overseas Highway in the beautiful coastal town of Islamorada, Florida. This unique institution offers a mix of delicious food, refreshing drinks, and a relaxed atmosphere perfect for unwinding and enjoying the ocean views. Whether you're craving a tasty meal or looking to sip on a cocktail while watching the sunset, Oceanside Safari is the perfect spot for locals and tourists alike. With its welcoming staff and inviting ambiance, this bar and restaurant is a must-visit destination for anyone looking to experience the true essence of Florida's coastal charm.

Morada Bay is a charming waterfront restaurant located at 81600 Overseas Highway in Islamorada, Florida. This institution offers a unique dining experience with stunning views of the bay and a laid-back atmosphere. Guests can enjoy delicious food and cocktails while soaking in the beautiful surroundings. Whether you're looking for a romantic dinner, a casual lunch with friends, or a special event venue, Morada Bay has something for everyone. Come and experience the flavors of Florida at this must-visit restaurant in the United States.

Lazy Days is an award-winning restaurant located in Islamorada, Florida, offering the freshest seafood in town. Enjoy oceanfront dining with exquisite Keys-style dishes such as seafood pastas, vegetarian options, sandwiches, certified Angus steaks, and chicken at reasonable prices. The restaurant has been voted "Best Restaurant Overall", "Best Waterfront Dining", "Best Seafood Restaurant", "Best Lunch", and "Best Wait Staff" in the Upper Keys People's Choice Awards. With spectacular views from tables nestled in the sand, an outside upstairs patio overlooking the Atlantic, and a cozy Keys-style atmosphere indoors, Lazy Days offers a unique dining experience. The full-service bar serves a variety of drinks, including craft beers, wines, and specialty cocktails. Don't forget to visit the Lazy Days Seafood Market for the freshest seafood in town and stop by the gift shop for custom t-shirts, hats, and more.

Pierre's Restaurant is a unique and elegant establishment located at 81600 Overseas Highway in Islamorada, Florida. The exterior of the two-story building is reminiscent of old colonial residences in West Africa, while the interior showcases a blend of different cultures from around the world. The restaurant boasts a sparkling white facade facing the Florida Bay, offering stunning views of sunsets. The Green Flash Lounge on the ground floor features a beautiful mahogany bar, leather sofas, beige banquettes, and rattan chairs. The dark planked wood floors, Indian arcade, and Moroccan, Indian, and African artifacts add to the ambiance of the dining room and lounge.

SandBar is a lively and vibrant institution located at 83413 Overseas Highway in Islamorada, Florida. This beachfront bar and restaurant offers a relaxed and casual atmosphere where guests can enjoy delicious food, refreshing drinks, and stunning views of the ocean. With a diverse menu featuring fresh seafood, mouth-watering burgers, and tasty appetizers, SandBar is the perfect spot to unwind and enjoy a meal with friends and family. Whether you're looking to grab a quick bite or spend a leisurely afternoon soaking up the sun, SandBar is the ideal destination for a memorable dining experience in the heart of the Florida Keys.

La Jolla Resort is an iconic lodging institution located at 82216 Overseas Highway in Islamorada, Florida, United States. Known for its "Old Florida" charm, the resort offers a front-row seat for stunning sunsets over the Florida Keys. Situated in the heart of the Purple Isle, guests are just moments away from all the island has to offer. Complimentary activities such as kayaking, biking, and fishing are available for the whole family to enjoy. The resort's multi-bedroom bayfront lodges offer modern luxury in a laid-back setting, perfect for families or groups. With Islamorada's unique beauty and wide-ranging attractions, La Jolla Resort is the perfect destination for a memorable Florida Keys getaway.

Islander Bayside Villas is a charming lodging institution situated at 81450 Overseas Highway in the picturesque town of Islamorada, Florida. Nestled along the beautiful bayside, this tranquil retreat offers guests a peaceful and relaxing atmosphere with stunning views of the water. The villas are tastefully decorated and equipped with modern amenities to ensure a comfortable stay for visitors. Whether you are looking for a romantic getaway, a family vacation, or a solo retreat, Islander Bayside Villas provides the perfect escape in the heart of the Florida Keys.

Located at 81801 Overseas Highway in Islamorada, Florida, Atlantic's Edge Restaurant is a culinary destination that offers a meal with a view. Overlooking the stunning Atlantic Ocean, this flagship seafood restaurant showcases the flavors of the Keys with a modern twist on island-inspired cuisine. Whether you choose indoor or outdoor dining, you can enjoy panoramic views while savoring dishes infused with local, fresh ingredients native to the Florida Keys. From breakfast to dinner, Atlantic's Edge serves up a diverse menu featuring everything from poached jumbo Gulf shrimp to Cuban-inspired dishes like guajillo braised short rib tacos. Indulge in decadent desserts like the chocolate sable tart or the rich key lime custard. Pair your meal with a refreshing cocktail from their extensive drink menu, including classics like mojitos and margaritas. With a relaxed yet elegant atmosphere, Atlantic's Edge Restaurant offers a unique dining experience that celebrates the flavors and cultural influences of the Caribbean and Atlantic islands.

Marker 88 is a popular bar and restaurant located at 88000 Overseas Highway in Islamorada, Florida. Known for its delicious food and refreshing drinks, Marker 88 offers a unique dining experience with stunning views of the ocean. In addition to their mouth-watering dishes, Marker 88 also has a boutique where guests can purchase souvenirs such as t-shirts, hats, craft sodas, and their famous key lime pie. Forgot to pick up a souvenir during your visit? Don't worry, you can shop online and have it shipped to you. Make your trip to the Florida Keys unforgettable with a visit to Marker 88.

Located at 80241 Overseas Highway in Islamorada, Florida, La Siesta Resort & Villas offers a tropical island style getaway with spacious guest rooms, beachside cottages, and private vacation homes. Experience authentic Keys life with island-inspired flavors and legendary cocktails while enjoying stunning sea views. The resort features lush private beaches, pools with ocean views, and fishing charters for the catch of your dreams. Accommodations include suites, cottages, and villas with idyllic Islamorada views and unique resort amenities. Special offers include discounts for Florida and Georgia residents, military personnel, and tax season rewards. Enjoy dining at Wild & Lime and nearby restaurants, as well as unforgettable experiences for special occasions. Plan your dream destination wedding or arrive at the Florida Keys marina for a seamless vacation experience. Explore all that La Siesta Resort & Villas has to offer and make memories to last a lifetime.

Located at 83409 Overseas Highway in Islamorada, Florida, the Chesapeake Beach Resort is a stunning seaside lodging destination that exceeds all expectations. As the Sport Fishing Capital of the World, Islamorada offers a relaxed atmosphere and year-round activities for guests to enjoy. Each room at the resort features comfortable beds and a tranquil ambiance, with the option to choose a Garden View room with a private balcony or upgrade to a suite or villa for added luxury. Surrounded by crystal blue waters and white sandy beaches, the resort offers a picturesque setting for a relaxing and breathtaking vacation.

Breezy Palms Resort is a charming lodging destination located in the beautiful Islamorada, Florida. Situated at 80015 U.S. 1, this tropical oasis offers guests a relaxing and unforgettable experience in the heart of the Florida Keys. With cozy accommodations, stunning ocean views, and a range of amenities including a pool, beach access, and on-site dining options, Breezy Palms Resort is the perfect choice for those looking to unwind and soak up the sun in paradise. Whether you're seeking a romantic getaway, a family vacation, or a solo retreat, this resort has everything you need for a memorable stay. Book your stay at Breezy Palms Resort and escape to a slice of paradise in Islamorada.

Hungry Tarpon Restaurant is a vibrant waterfront bar and restaurant located at 77522 Overseas Highway in Islamorada, Florida. This institution offers a delicious escape with a menu featuring the ocean's bounty, including signature dishes like Tuna Sliders, Mahi Reuben, and Pan Seared Salmon. Guests can enjoy their meals while watching the sun rise and feeding the Tarpon in the distance. In addition to mouthwatering seafood options, Hungry Tarpon Restaurant also offers a variety of cocktails, including the famous Trailer Trash Bloody Mary. The menu includes a range of options from breakfast items like glazed donut French toast to seafood dishes like blackened shrimp tacos and lobster mac and cheese.

Dockside Raw Bar & Grill is a charming waterfront restaurant located in the picturesque town of Islamorada, Florida. Situated at 90311 Old Highway, this institution is a popular destination for locals and tourists alike. Known for its fresh seafood and laid-back atmosphere, Dockside Raw Bar & Grill offers a variety of delicious dishes, from oysters on the half shell to grilled fish tacos. Guests can enjoy their meal while taking in stunning views of the marina and sipping on handcrafted cocktails. Whether you're looking for a casual lunch or a romantic dinner by the water, Dockside Raw Bar & Grill is the perfect spot to satisfy your cravings.

Coastal Vacation Rentals of the Florida Keys is a premier real estate and travel agency located at 82889 Overseas Highway in Islamorada, Florida, United States. We specialize in luxury vacation homes that exceed your expectations and cater to all your needs. Our extensive inventory includes weekly and monthly rentals, condos, villas, estates, corporate retreats, oceanfront and bayfront properties. Our personalized service sets us apart, ensuring that your vacation is a success no matter where you choose to stay in the Florida Keys. From breathtaking views to top-notch amenities, we have everything you need for a memorable getaway. Whether you're looking for a romantic escape or a family adventure, we have something for everyone.

Solfinis Sunset Cruise is a premier travel agency located at 84001 Overseas Highway in Islamorada, Florida. Specializing in unforgettable sunset cruises, we offer a luxurious and relaxing experience on the beautiful waters of the Florida Keys. Our expert staff will ensure that every detail of your cruise is perfect, from the stunning views to the delicious cocktails served on board. Whether you're looking for a romantic evening with your loved one or a fun outing with friends, Solfinis Sunset Cruise is the perfect choice for a memorable experience on the water. Book your cruise today and prepare for an unforgettable journey into the sunset.

Sea The Keys Island Adventures is a premier travel agency located in the beautiful coastal town of Islamorada, Florida. Specializing in unique and unforgettable island adventures, our team of experienced professionals is dedicated to providing top-notch service and creating unforgettable experiences for our clients. Whether you're looking to explore the stunning underwater world of the Florida Keys, embark on a thrilling fishing excursion, or simply relax on a pristine beach, Sea The Keys Island Adventures has something for everyone. Let us help you plan the perfect island getaway and make memories that will last a lifetime.

Saylor Cafe is a charming and cozy eatery located at 79851 Overseas Highway in Islamorada, Florida. This quaint cafe offers a delightful dining experience with a menu featuring a variety of delicious food options. From freshly brewed coffee to mouthwatering pastries and hearty sandwiches, Saylor Cafe has something for everyone. Whether you're looking for a quick bite to eat or a relaxing meal with friends and family, this cafe is the perfect spot to enjoy a tasty meal in a welcoming atmosphere. Visit Saylor Cafe today and treat yourself to a delightful culinary experience in the heart of Islamorada.

The Maison is a charming and elegant institution located at 80639 Old Highway in Islamorada, Florida. With a prime location in the heart of the Florida Keys, this institution offers a luxurious and tranquil escape for guests looking to relax and unwind. The Maison boasts stunning views of the ocean and is just a short distance from some of the area's best attractions, including world-class fishing, snorkeling, and dining options. Whether you're seeking a romantic getaway, a family vacation, or a solo retreat, The Maison provides a welcoming and sophisticated atmosphere for all guests to enjoy.

The Beach Cafe & Bar is a charming seaside establishment located at 81600 Overseas Highway in Islamorada, Florida. With its laid-back atmosphere and stunning ocean views, it is the perfect spot to relax and enjoy a delicious meal or refreshing drink. Whether you're looking for a casual lunch with friends or a romantic dinner by the water, The Beach Cafe & Bar has something for everyone. Come experience the beauty of the Florida Keys while savoring tasty dishes and cocktails at this waterfront gem.