10 Best Places to Eat in Key West for the Ultimate Staycation

Key West is famous for its laid-back island vibe, turquoise waters, and vibrant local culture. But for those planning a staycation in this tropical paradise, the food scene is an experience all its own. Whether you’re a local looking for new dining spots or a visitor staying longer than expected, here’s a roundup of the 10 best places to eat in Key West that will turn your staycation into a culinary adventure.

1. Blue Heaven

Located in the heart of Old Town, Blue Heaven is a quintessential Key West experience. Famous for its lush outdoor seating and live roosters wandering through the garden, this spot is perfect for brunch lovers. From their mouthwatering lobster Benedict to the iconic key lime pie, Blue Heaven offers an eclectic menu that showcases the island’s fresh ingredients.

2. El Siboney

For those craving authentic Cuban flavors, El Siboney is a must-visit. Tucked away in a quiet part of town, this unassuming eatery serves up hearty portions of traditional Cuban fare, like ropa vieja and arroz con pollo. Locals rave about the authentic vibe and home-style cooking, making it an excellent spot to enjoy a relaxed dinner during your staycation.

3. Eaton Street Seafood Market & Restaurant

If fresh seafood is on your mind, Eaton Street Seafood Market delivers. Grab a seat at their casual outdoor patio and feast on local favorites like conch fritters, shrimp po’boys, and grilled lobster tails. For those cooking at home, this market also sells the day’s catch, so you can bring the taste of Key West right to your kitchen.

4. Santiago’s Bodega

A cozy tapas restaurant, Santiago’s Bodega offers a unique experience for staycationers wanting to share bites with friends or family. Their small plates, like bacon-wrapped dates and lamb patties, paired with a robust wine list, create a charming and intimate dining atmosphere. It’s the ideal spot for a long, leisurely meal to escape the everyday hustle.

5. Garbo’s Grill

This food truck may be small, but it packs a big flavor punch. Garbo’s Grill serves creative fusion dishes, including Korean BBQ tacos and ahi tuna burritos. With its funky, laid-back vibe and outdoor seating, it’s a favorite among locals for a quick yet unforgettable meal. Grab your food to-go and enjoy a picnic at the nearby Smathers Beach for the ultimate Key West staycation experience.

6. The Lobster Shack Key West

Key West is synonymous with lobster, and The Lobster Shack celebrates this crustacean in style. Known for its lobster rolls, this charming shack serves both cold and warm varieties, allowing you to choose your favorite. The setting is casual, but the food is top-tier, perfect for a laid-back afternoon meal after exploring the town.

7. Cafe Sole

A local favorite for more than 20 years, Cafe Sole combines French cuisine with the best local seafood. Their signature dish, hogfish snapper, is a must-try. The intimate atmosphere and stellar service make this spot ideal for a romantic dinner or a quiet evening to unwind on your staycation.

8. Latitudes

For a truly unforgettable dining experience, take a short ferry ride to Sunset Key and enjoy dinner at Latitudes. The restaurant offers upscale dining with breathtaking ocean views, making it one of the most scenic dining spots in Key West. Whether you’re indulging in fresh seafood or sipping on cocktails while the sun sets, this is a dining experience worth splurging on during your staycation.

9. Matt’s Stock Island Kitchen & Bar

Located just outside the main drag of Key West on Stock Island, Matt’s Stock Island Kitchen & Bar is a hidden gem that offers a relaxed, waterfront dining experience. Their menu focuses on comfort food with a local twist, from shrimp and grits to their famous fried chicken. It’s a great spot to enjoy a lazy weekend brunch while soaking up the Florida sun.

10. A&B Lobster House

A&B Lobster House is a Key West institution for fine dining. Overlooking the marina, it’s a great spot for a romantic dinner or a celebratory meal. Their extensive menu includes classic seafood dishes, such as lobster thermidor and shrimp scampi. If you’re a fan of refined seafood and elegant dining, this is the perfect place to wrap up your Key West staycation in style.

Staycation Dining Tips

Whether you’re savoring fresh seafood by the beach or trying Cuban delicacies in the heart of Old Town, these ten spots will enhance your staycation by providing a diverse range of flavors. Here are a few tips to make your dining experience even better:

• Book reservations in advance: Many Key West restaurants are popular, especially during peak times. Make sure to reserve a table early for places like Latitudes or A&B Lobster House.
• Check out local happy hours: Many restaurants offer excellent happy hour specials, where you can sample local drinks and small plates at a lower cost.
• Explore food trucks: Don’t underestimate the power of a good food truck in Key West. Places like Garbo’s Grill offer some of the best food on the island with a casual, fun atmosphere.

From the best seafood joints to cozy hidden gems, these ten restaurants will elevate your Key West staycation, making it a deliciously memorable experience. Book your Key West staycation rental with Whimstay today!

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