Eat And Sleep Your Way through The Florida Keys

Sunny, tropical, cheerful and relaxed- that is the island vibe of the Florida Keys.

A short drive from nearby Miami and surrounded by water, the Keys are the perfect place for any seafood gluttons who want to eat their way through the island and spend their nights lounging with drinks in hand on a porch surrounded by palm trees. The islands are dotted with a combination of charming inns and B&Bs as well as familiar hotel chains but each place is as unique as each of the islands of the Keys. Prepare to slow down to nearly a standstill and adopt the Island time that can turn the Florida Keys into an annual pilgrimage for many!

Chelsea House Hotel

Located in the Old Town area of Key West, the Chelsea House comprises two estate properties built in the Victorian and Queen Anne styles. Tropical gardens and large palm trees shade this adorable hotel where you can enjoy an outdoor pool and free continental breakfast. You’re just two blocks from the laid-back but bustling Duval Street, home to some fantastic restaurants and bars.

Chelsea House Pool & Gardens Hotel

Key West
7.7 Good (296 reviews)

Hyatt Place at Faro Blanco Resort & Yacht Club

Captains, prepare to drop anchor at the landmark Marathon Island’s Faro Blanco Resort & Yacht Club. The bayside village boasts a 125 room Hyatt Place hotel with easy docking facilities for those coming by boat. The historic facility is truly an all-encompassing Keys experience with a vibe of laid-back luxury.

Casa Morada

Want to enjoy a slice of seclusion? The beautiful, all white, 16 suite Casa Morada is surrounded by a lush tropical landscape and enjoys its own private islands, with a pool and gazebo bar which is accessed by a drawbridge. Suites, decorated with Mexican antiques and modern accents, have spectacular views of either the landscaped gardens or the Florida Bay. Join a morning yoga class by the sea or unwind underwater with a scuba diving session.

Casa Morada

Top rated
9.4 Excellent (668 reviews)

Tranquility Bay Beach House Resort

Overlooking the sparkling waters of the Gulf of Mexico, Tranquility Bay Beach House Resort brings the shine of the water straight to your door. Relax on your porch and look out onto the water or cool down inside the beach houses which have two or three bedrooms and plenty of space to stretch out. Outside you’ll be able to stretch as well, with a two and a half acre white sand beach, a rare gem on these islands but opportunities for fishing, diving and snorkeling. If you prefer to stay out of the salt water there’s also three onsite swimming pools and 12 acres of manicured tropical gardens.

Tranquility Bay Resort

Top rated
Fort Myers Beach
8.8 Excellent (2393 reviews)

Casa Marina

The Keys might not be known for its beaches, but Casa Marina, one of the island’s oldest running hotels, has the Key’s biggest private beach on top of two incredible swimming pools and a luxurious surrounding landscape. You’re a short walk from the jovial yet chill nightlife and shopping of Duval Street. The building, listed on the National Register for Historic Places, is a secluded gem that has long attracted celebrities and historical figures to its hallowed halls.

Casa Marina Key West, Curio Collection by Hilton

Key West
6.9(11359 reviews)

Where To Eat

A veritable melting pot of cultures including Bahamians, Cubans, New Englanders and other internationals have contributed to the delicious Florida Keys‘ cuisine. An abundance of seafood shapes the base for most meals: pink shrimp, the mollusk conch, stone crabs, mahi-mahi and yellowtail snapper make up the regional delicacies and figure prominently on locals menus. For dessert, Key lime pie is still a staple, both for locals and visitors. Dining here is as easy-going as the locals and is sure to be an inviting affair at any restaurant you visit.

Blue Heaven

Tucked away among lush tropical scenery is locally-loved Blue Heaven. This offbeat restaurant is home to several chickens, cats, tropical trees, live music most nights and a free spirited kitchen vibe with staples that have people always returning for more. Enjoy some Caribbean BBQ shrimp, deglazed with Red Stripe beer for an alfresco dinner or come for lunch and have the Loaded Black Bean Bowl with Corn Bread. The menu is a tantalizing mix of Mediterranean, Caribbean and new-American and the laid-back island atmosphere means you’ll enjoy your food as much as you would eating it from the comfort of your couch. Their Key lime pie is worthy of a sampling as well!

Conch Republic Seafood Company

When you’re surrounded by the sea, it’s only natural that the specialty here would be seafood-heavy. The islands are perhaps best known for the delightful and delicious Conch, which figures prominently on the menus of many restaurants. Get a taste at Conch Republic Seafood Company which has retained its history as a shrimp processing plant with giant tanks containing the fruits that the sea bears. The produce here is fresh — straight off the boat dock and the seafood will basically melt in your mouth.

El Siboney Restaurant

You can’t get this close to Cuba without trying out some authentic Cuban food. El Siboney serves up traditional home-cooked style Cuban meals to those willing to venture off the beaten path of Duval street — those who do are rewarded: oxtail with rice and plantains, classic Cuban sandwiches, conch chowders and be sure to get absolutely everything with an extra side of plantains.

Ma’s Fish Camp

There is a lot of beef regarding the best slice of Key lime pie on the Keys. This beloved dessert has hit the international stage with many variations:whipped cream or meringue topping? And for the crust, graham cracker or pastry? The color is yellow on the Keys, and the best one comes courtesy of Ma’s. Find this sweet restaurant at Mile Marker 81.5 on Islamorada and you won’t be disappointed by their award-wining version of the dessert: Graham cracker crust, tangy filling and topped with a delightful meringue.

Half Shell Raw Bar

If you’re looking to spice things up with the Florida Key’s best natural aphrodisiac, head to Half Shell Raw Bar. This is the classic raw bar experience and an obligatory must do for anyone who enjoys fresh seafood. The restaurant has been around since 1973 and is the site of local oyster shucking competitions — so you know they’re taking it seriously. Grab a seat on the picnic tables for the best ocean view and while oysters may have your main draw, their stuffed seafood entrees are a winner as well.

Cafe Marquesa

For a date-night meal that will blow you away, make a reservation at Café Marquesa. The interior is small but elegant, especially for the Islands and the attention to detail in the food is outstanding. The seafood on the menu is slightly shaped by the season, but there is plenty of eat for those who prefer turf to surf: Grilled Black Angus Filet Mignon or even a Vegetarian Feast if you’re feeling something lighter. One thing is for sure: it will be a memorable meal for any foodie.