The Florida Keys & Key West are a slice of paradise just a short drive from Miami. The Keys, which stretch over 125 miles, offer a secluded waterfront getaway surrounded by natural wonders, with activities like fishing, diving and, of course, fine dining. Pack your weekend bags, drop the top and dive into turquoise waters, exploring the Florida Keys’ and Key West’s most desired getaways.
Where to Stay
Little Palm Island
Aerial view of a Bungalow Suite at Little Palm Island
Photo Courtesy of Little Palm Island
Accessible only by seaplane or private boat, Little Palm Island is a crown jewel of the Florida Keys. Florida’s only three-Michelin Key property, this adults-only, four-acre private island resort features 30 charming beachfront bungalows inspired by the British West Indies, candlelit dinners and spa treatments that beckon a true romantic escape. Expect crushed seashell paths, romance and the utmost tranquility. 28500 Overseas Hwy., Little Torch Key, littlepalmisland.com
Cheeca Lodge & Spa
With just the right amount of Florida flair, Cheeca Lodge offers a resort-forward approach set along the sandy shores. Located on Islamorada, the resort has remained a cornerstone of the community on the island since 1946. Set on 27 acres, the resort boasts 254 guest rooms, a wooden fishing pier, three on-site restaurants, and a spa for unwinding after a day out on the water. 81801 Overseas Highway, Islamorada, cheeca.com
Isla Bella Beach Resort
One of the Keys’ major attractions is the water, and Isla Bella makes it easy: every room and suite boasts expansive oceanfront views. Located on the threshold of Seven Miles Bridge, Isla Bella is framed by lush greenery and one mile of waterfront beach. Guests can enjoy five oceanfront pools, a 4,000-square-foot spa and a quintessential Florida Keys experience on the water. 1 Knights Key Blvd., MM 47, Marathon, islabellabeachresort.com
The Marquesa Hotel
Located in the historic Old Town Key West district, The Marquesa Hotel offers all the charm associated with Key West. The 44-suite hotel exudes classic Keys charm and old-world refinement through its historic architecture and modern tropical design. Relax in the lush garden courtyards surrounding three sparkling pools and dine at Café Marquesa, one of the island’s fine-dining treasures. 600 Fleming St., Key West, Florida Keys, marquesa.com
Ocean Key Resort & Spa
Nestled between Key West Harbor and Mallory Square, where historic Duval Street begins the old town experience, sits Ocean Key Resort & Spa—a luxurious oceanfront property in the heart of Key West, home to the world-famous Sunset Pier. Overlooking the turquoise waters of the Atlantic, the resort embodies the charm, energy and eclectic vibe of Key West. The rooms draw inspiration from tropical living with local art and eclectic design, while the hotel features luxury amenities and the Hot Tin Roof Waterfront Restaurant, known for its exquisite cuisine and stunning sunset views. Zero Duval, Downtown Key West, oceankey.com
Hawks Cay Resort
Photo Courtesy of Hawks Cay Resort
Set on the secluded island of Duck Key, Hawks Cay Resort has been part of the Keys for over 40 years. All 177 rooms and suites are effortlessly suited for the island lifestyle. Mirroring the surrounding seascape, each room feels like a serene sanctuary, framed by views of swaying palms, tropical landscaping and crystal waters. Recently renovated, the hotel unveiled reimagined boat slips for yachts up to 91 feet. Guests can dine at Salt Ash, helmed by Michelin-starred chef Jeremy Ford and relax at the enhanced Calm Water Spa. 61 Hawks Cay Blvd., Duck Key, hawkscay.com
Ombi
A floating hotel, yes, please. Ombi offers a serene, off-grid experience in Key Largo—a trio of upscale private bungalows, set in an overwater villa. Guests are surrounded by water, and each bungalow includes a kayak and a paddleboard. If staying at Ombi, hot meal delivery, sunset cruises, jet skiing and scuba diving are all available upgrades. 101425 Overseas Highway, Key Largo, stayombi.com
Islander Resort
Photo By Kris Tamburello
The Islander Resort in Islamorada sits on 24 oceanside acres
Set in the heart of Islamorada, the property exudes vintage charm. Offering a slice of paradise, the resort spans 24 acres, blending adventure and relaxation. With rooms facing the bay and ocean, travelers will have no shortage of activities to choose from. For adventure seekers, Islander guests can paddleboard along the reef, snorkel the sandbar or take a sunset cruise. For those looking for a more relaxed experience, enjoy private cabanas or morning yoga. 82100 Overseas Highway, Islamorada, islanderfloridakeys.com
La Concha Autograph Collection
Celebrating its 100th anniversary, La Concha remains a showpiece of Key West’s history. Hosting icons such as Ernest Hemingway, Tennessee Williams, President Harry S. Truman and even rumored Al Capone, the hotel preserves 1920s glamour and architecture. The hotel, which recently completed a full renovation, is a pink paradise for an island getaway.430 Duval St., Key West, laconchakeywest.com
Where to Explore
Ernest Hemingway Home and Museum
One of Key West’s most popular destinations, the Hemingway House not only celebrates the American author, but it's also part of history. Registered as a National Historic Landmark, the home and museum are filled with memorabilia, honoring the man who inspired a generation of writers.
Guests can enjoy guided tours every 15 minutes, which include the writing rooms, one of the main attractions. Also on site, many six-toed cats are said to be descendants of Hemingway’s cat. 907 Whitehead St., Key West, hemingwayhome.com
Duval Street
Originally developed as part of Old Town in Key West, Duval Street. has a rich history and remains one of the most iconic streets in the Florida Keys. The premier hub for dining, nightlife and entertainment, Duval Street draws crowds year-round. Whether grabbing a drink, enjoying a piece of pie, sipping coffee or browsing art galleries, Duval Street is historically a must-visit.
Seven Mile Bridge
Not just a drive, the Seven Mile Bridge is a landmark that spans the Florida Keys. The original bridge, built in 1912, helped link the Keys to Key West. A highlight of the scenic Florida highway, the bridge is far more than a scenic drive. Paralleling the current bridge is the original structure, which was damaged by a hurricane and is listed on the National Register of Historic Places, serving as a world-famous fishing pier.
