Best Cuban & Caribbean Restaurants in Key West

Did you know Key West, Florida, is closer to Cuba than it is to the mainland of the United States? Since the islands are just 90 miles apart, it should be no surprise that we have an intertwined history and heritage. One of the most evident connections today is our island cuisine, which is heavily influenced by the unique flavors of Cuba, the Bahamas and many other island neighbors. Many of our best restaurants offer Caribbean influenced and Cuban cuisine.  Let our Rent Key West Vacations team of local experts help you find the best Caribbean and Cuban restaurants in Key West!  Here are just a few of our favorites to wet your appetite:

El Meson de Pepe

El Meson de Pepe has served authentic Cuban food in Key West’s Mallory Square for over 30 years! They have a beautiful Patio Bar where you can enjoy a refreshing cocktail while listening to live salsa music as the sun goes down over the adjacent, nightly Sunset Celebration. They offer fantastic combination plates where you can sample three of their most popular dishes in one order. For over 30 years, Chef Pepe Diaz and his family have been dedicated to pristine quality, authentic Cuban Cuisine, and the preservation of Cuban Conch Heritage in Key West. Buen Provecho!

El Siboney Restaurant

El Siboney in historic Old Town has been recognized as one of Key West’s best Cuban restaurants since 1984. The family owned and operated establishment offers traditional Cuban home cooking & housemade sangria in a casual, family-friendly setting.  Their most popular dishes include roast pork sliced, topped with onions and served with a choice of rice, sweet plantains and Cuban bread. Other favorites include the Siboney steak, a Cuban mix sandwich  and Paella Valenciana.

Kaya Island Eats

Their name says it all; fresh island inspired dishes.  Enjoy their signature Tuna Nachos Pokee or the Incredible Jamaican Jerk Chicken Wings with Goat Cheese Jerk Sauce & Green Onion to start.   The Legendary Rasta Pasta with Macadamia Nut Jerk Pesto is amazing on its own, but you  can add chicken, shrimp, veggies and/ or portobello mushrooms.  They also offer Carne Asada Steak Tacos and other beef and pork dishes.

Frita’s Cuban Burger Cafe Key West

Photo Credit: Nick Doll

This Quaint, quirky Cuban kitchen with outdoor seating is doling out way more than just authentic Frita Burgers!  The Frita is a heavenly burger with origins in 1930’s Cuba. The burgers are a mouthwatering blend of beef and pork burger seasoned with Spanish spices and topped with a special sauce and crispy fried julienne potatoes, all sandwiched on a Cuban bun. They also serve classic Cuban cuisine and homemade pastries and locally crafted ice cream!  Local Secret:  Some of Key West’s best musicians pop in later in the evening to jam on the patio!

Blue Heaven Floridean-Caribbean Cuisine

This Iconic landmark offers Floridean-Caribbean cuisine & key lime pie in a funky outdoor setting with live music.  It is quirky and fun, but the food is taken very seriously.  One taste of the blueberry pancakes, carrot and curry soup, miso-marinated eggplant salad or the scallops provencal will prove that fact to be true.  Check out our friends: Broadway Diva Teri White and the Broadway Pitboss & Music Man Larry Baeder when they perform.  They are two of Broadway’s Best who have made Key West their home!

Key West Cottages, Condos & Vacation Home Rentals

After enjoying delicious food at Caribbean inspired & Cuban restaurants in Key West, return to your vacation home on the island. Rent Key West Vacations offers properties with everything you need, including fully equipped kitchens, linens, and laundry facilities. We also offer Key West vacation rentals with private pools, ocean views, and easy access to the beach. Escape to Key West today!

Your Guide to Key West Museums

Key West, Florida, attracts beach lovers, water & eco adventurers, foodies & nightlife enthusiasts, and seekers of spectacular sunsets. Visitors can also discover a confluence of history, art, and culture at our museums. Stay with Rent Key West Vacations and enjoy easy access to Key West’s museums.

Discover Key West Art, Architecture & History

Explore Key West Maritime Museums

Key West, located between the Gulf of Mexico and the Atlantic Ocean, has a rich maritime history which can be discovered at one of these museums:

Learn About Famous Key Westers

Key West has attracted presidents, artists, and authors. Visit their historic homes:

  • The Hemingway Home & Museum: is filled with photos, books, and antiques. Greet the six-toed cats and view the swimming pool, which was an extraordinarily rare construction feat and luxury in 1930s Key West.
  • Truman’s Little White House: is Florida’s only Presidential Museum and was known as the Winter White House from 1946-‘52.  Constructed in 1890 as naval officers’ housing, it features artwork, photographs, antiques, and artifacts.
  • Tennessee Williams Museum: offers a collection of the great American playwright’s original works, photos, and memorabilia.   
  • Meet Robert the Doll at Fort East Martello Museum: Once you have paid homage to Key West’s most renowned “haunted” resident, you are entitled to blame all of your vacation shenanigans on Robert!  The museum offers art, history, and an expansive view of Key West and the ocean from the fort’s tower.

Stay in Our Key West Vacation Rentals

Discover history, art & architecture, and famous residents at one of Key West’s museums. Whether you want to stay in the heart of the old town historic district or near the beach, we have a property that is perfect for you and close to everything Key West has to offer!

Family Vacation: Things to Do in Key West with Kids

It’s time to pack your family’s bags and head to the southernmost point in the United States for an epic Florida Keys getaway. Key West is a vibrant island paradise offering picturesque beaches, endless watersports, historic sites, fascinating museums, and plenty of activities for our youngest visitors. Discover the best things to do in Key West with kids, from snorkeling with marine life in our turquoise waters to walking among hundreds of colorful butterflies. When you are ready to book your trip, you can rest assured that Rent Key West Vacations has the perfect vacation rental for your family! Read on to learn more about our favorite experiences for families on and around the island of Key West.

Beaches & Water Activities for Families in Key West

Key West is a unique location where the Atlantic Ocean and the Gulf of Mexico meet, which means there are unlimited ways to have fun on the water. Popular watersports include scuba diving, snorkeling, parasailing, fishing, jet-skiing, and paddling. Rent your equipment from local companies like Sunset Watersports and Fury Key West Watersports. And if you are looking for the best beach to take the family to, we recommend:

The Top Things to Do in Key West with Kids

After you have spent time exploring the water, shake off your sea legs and discover endless things to do in Key West with kids:

  • Key West Aquarium: Get up close and personal with Key West’s native marine life at the aquarium. Head to the touch tank to interact with marine life like sea urchins and conchs. There are also exhibits with sharks, sea turtles, and jellyfish where you can watch daily feedings, sign up for tours, and learn about conservation.
  • Key West Butterfly and Nature Conservatory: This attraction allows visitors to stroll through a state-of-the-art enclosed tropical garden as 60 varieties of beautiful butterflies flutter around you.
  • Conch Tour Train: Sign up for a “train” ride around Old Town Key West and see the best landmarks in town. The tour is led by a local guide who will take you on a journey through time with stories of local legends and fun history.
  • Key West Shipwreck Museum: This is a one-of-a-kind Key West experience that will take you back to 1856 when the Isaac Allerton shipwrecked along the Florida Keys reef. The experience combines actors, films, and authentic artifacts to tell the tale of the shipwreck.
  • Dry Tortugas: Although technically not on Key West, this National Park is worth the extra boat trip or seaplane excursion. The park is home to historic Fort Jefferson and some of the best snorkeling in North America.
  • Don’t leave Key West without taking a family photo at the Southernmost Point buoy!

Spacious Key West Vacation Homes for Families

Escape to our tropical paradise and discover all the fun things to do in Key West with kids. Rent Key West Vacations offers everything you need to plan a successful family getaway with our collection of over 65 vacation rentals and convenient concierge services. Whether you want to stay in the heart of the historic district or near the beach, we have the perfect Key West vacation home for every family!