Florida Keys Holidays 2025 & 2026 • Browse Popular Itineraries
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Florida Keys Holidays 2025 & 2026 This sun-drenched archipelago offers a little slice of paradise…

Florida Keys Holidays

If you’re looking for a taste of laid-back island life, then the Keys fit the bill. Journey through palm-fringed islands, cruising over the scenic Overseas Highway – from Key Largo’s coral reef, down to the party town of Key West.

  • Key Largo and the Upper Keys – The pristine beaches, warm waters and spectacular coral reef are ideal for watersports or a beachy escape.
  • Marathon and the Middle Keys – Experience incredible wildlife encounters and take in the breathtaking scenery.
  • Key West and the Lower Keys – The rich culture and buzzing, yet relaxed, atmosphere offer the quintessential Florida Keys experience.

Experience the Florida Keys on its own or combine it with another American destination – your FREEDOM Travel Consultant will be pleased to assist you.

Plan your holiday
Freedom Destinations Travel Specialist

Free Planning Service

Tell us where you want to go and what you would like to do and we will create your perfect holiday – at a price you can afford.

call us on 0333 234 0922

Freedom Destinations Travel Specialist

Free Planning Service

Tell us where you want to go and what you would like to do and we will create your perfect holiday – at a price you can afford.

call us on 0333 234 0922

Florida Keys Holidays

The Florida Keys are a collection of hundreds of islands, stretching 200 kilometres into the Gulf of Mexico. Although it is expansive, the most popular islands include Key Largo, Islamorada, Marathon, Big Pine Key, and famous Key West. The Keys has lots to offer, with dazzling white sand beaches, miles of coral reef, fascinating historical sites, and even a buzzing nightlife.

The most popular way to explore this archipelago is by car, taking a stunning road trip across the iconic Overseas Highway.

How long does it take to drive the Florida Keys?

If you pick up your car from Miami Airport, it is 160 miles to the Lower Keys.

You can make the drive from Miami to Key West in as little as one day, but we recommend opting for slower travel, and soaking up all that the Keys has to offer. Perhaps opt for an 11 Day Fly Drive?

What is the best time of year to visit the Florida Keys?

March to May – Spring in the Florida Keys offers comfortable temperatures (in the high 20°Cs) and prime waters for swimming, snorkelling, diving and fishing.

June to October – The weather is more unpredictable, with high levels of humidity and rainfall, but you can get some great deals on hotels.

November to February – Boasts the Keys’ driest and most mild weather, which ideal for outdoor activities, and you can enjoy a bustling calendar of cultural events.

Things to do in Key Largo and the Upper Keys:

  • John Pennekamp Coral Reef State Park – incredible for snorkelling and scuba diving, or take a kayak tour through the mangroves or a glass-bottom boat tour.
  • Morada Way Arts & Cultural District – explore six blocks of lively galleries, studios, bars and restaurants.
  • Islamorada Sandbar – enjoy pristine sands, panoramic views and an electric atmosphere as the sandbar quickly attracts a boat party.

Things to do in Marathon and the Middle Keys:

  • Bahia Honda State Park – explore white-sand beaches, crystal clear waters and the old rail road bridge, offering incredible views.
  • Turtle Hospital – learn about the hospital’s critical conservation work and even watch the rehabilitated turtles be released.
  • Sombrero Beach – relax on one of the most beautiful beaches in the Keys.

Things to do in Key West and the Lower Keys:

  • Mallory Square sunset celebration – musicians and performers flock to the square each evening for a night of entertainment and festivity.
  • Ernest Hemingway Home and Museum – uncover the past of a literary legend.
  • Dry Tortugas National Park – Fort Jefferson contrasts beautifully against the white sands, turquoise waters and coral reefs.
  • Southernmost Point Buoy – visit the most southerly point of the continental U.S.
  • National Key Deer Refuge – look out for the Lower Keys’ unique species: Key Deer.
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