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Aerial view of the Seven Mile Bridge that leads to the famous Florida Keys, stretching out into the distance across the aqua blue ocean in Florida, USA

Florida Keys Holidays


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Florida Keys holidays offer the chance to discover over 100 sunshine drenched islands, strung far out into the warm blue waters of the Gulf of Mexico.

Easily accessible from Miami, and connected by the scenic Overseas Highway, hop between Key Largo, Marathon and Key West – and other islands – to discover world class diving, fascinating wildlife and a unique, laidback atmosphere.

Trailfinders offers a range of Florida Keys holidays and our expert travel consultants are a mine of information about what to do here, often with first-hand travel experience. Whether you want to cruise along the Overseas Highway on your Florida honeymoon, soak up the relaxed ambiance of the Florida Keys after a busy few days exploring Orlando’s theme parks or combine with an all-encompassing Florida fly drive holiday – they are the perfect people to ask.
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OUR HOLIDAYS TO THE FLORIDA KEYS

Nobody offers more ways to explore the Florida Keys than Trailfinders.

Here's a snapshot of some of our most popular Florida Keys holidays. If you don’t see what you’re looking for, click on the link below them to see our complete range of holidays and tours in the destination.

If you'd like to see how you could fit the Florida Keys into a wider exploration of the United States, take a look at our USA Holidays pages.
Highway to Hemingway
Highway to Hemingway
Fly Drive Holiday
12 days / 11 nights

Coast above the warm waters and magical coral reefs of the Florida Keys, hopping from island to island as you relax, unwind and cruise along the spectacular Overseas Highway.

Guide Price: €2,849 £2,499 pp

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Unique & Boutique Florida
Unique & Boutique Florida
Fly Drive Holiday
19 days / 18 nights

From glamorous tree-lined boulevards to quirky seaside towns, unspoiled islands and little known pockets of history, Florida is full of surprises.

Guide Price: €4,899 £4,299 pp

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Luxury Florida
Luxury Florida
Fly Drive Holiday
16 days / 15 nights

Sitting waterside, toes dipped in crystal clear waters, it’s easy to see how Florida’s relaxed tempo is just the tonic for a fast-paced life.

Guide Price: €4,099 £3,499 pp

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Wild Florida
Wild Florida
Fly Drive Holiday
18 days / 17 nights

Discover Florida’s natural wonders and encounter its enchanting wildlife on this unique adventure.

Guide Price: €2,679 £2,225 pp

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Wildlife & Waterbabies
Wildlife & Waterbabies
Family Holiday
14 days / 13 nights

From sunrise fishing trips to sunset snorkelling, the Florida Keys are perfect for families looking for a bit more action with a hint of barefoot luxury.

Guide Price: €1,535 £1,289 pp

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Miami & the Florida Keys
Miami & the Florida Keys
Honeymoon
12 days / 11 nights

Revel in the dynamic Latin vibe of Miami before swapping high-tempo city life for the calm, turquoise blue waters and romance of the Florida Keys.

Guide Price: €2,169 £1,845 pp

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WHERE TO GO IN THE FLORIDA KEYS

Each of the Florida Keys boasts its own attractions and appeal: from lively Key West known for its fun filled street entertainment and spectacular sunsets to the self-proclaimed dive capital of the world – Key Largo. Or maybe you’d like to spend time relaxing on the beautiful laid back islands of Marathon and Duck Key?

Take a look at the destination guide below the Florida Keys map for more details on each holiday destination. Alternatively, if you are looking for some inspiration for your Florida Keys holiday, give us a call and speak to one of our expert travel consultants.
Key West
Key West
Located at the southernmost point in the USA, Key West has a lively and fun atmosphere with legendary sunset celebrations at Mallory Square featuring sword swallowers, street dancers and sundowners; a fantastic place for snorkelling and diving.
Marathon & Duck Key
Marathon & Duck Key
The island communities of Marathon and Duck Key are a collection of small islands in the mid-point of the Keys boasting excellent fishing, kayaking and paddle boarding and fascinating places such as the Dolphin Research Centre and Turtle Hospital.
Islamorada
Islamorada
Nestled between Duck Key and Key Largo, Islamorada’s village of islands offers excellent deep sea fishing and shallow reefs, perfect for divers and snorkelers alike.
Key Largo
Key Largo
Key Largo is situated 60 miles south of Miami and is the self-proclaimed dive capital of the world – home to marine sanctuaries and state parks, including the 510ft USS Spiegel Grove (a huge artificial reef), the surrounding waters are teeming with colourful marine life.
Overseas Highway
Overseas Highway
Stretching down to the southernmost tip of Highway 1, this incredible route connects lively Miami with its laidback, yet vibrant cousin, Key West via beautiful stepping stones of limestone islands.
Marine Parks
Marine Parks
The various marine parks situated throughout the Keys are a must for those with a passion for water sports and marine life.

OUR RECOMMENDED HOTELS IN THE FLORIDA KEYS

We feature a great range of accommodation in the Florida Keys, with something to suit all budgets. Maybe you’re looking for a chic oceanside resort on a laidback island or a stylish resort just a few minutes from bustling downtown Key West.

What you won’t find here are thousands of Florida Keys hotels to wade through. We have done the hard work for you and selected the best places to stay and our travel consultants are on hand to help you plan your Florida Keys holiday, often with first-hand experience.
Ocean Key Resort & Spa
Ocean Key Resort & Spa
4 star

The Keys

This lovely resort reflects island living with its laidback pace and bags of charm.
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Havana Cabana, Key West
Havana Cabana, Key West
3 plus star

The Keys

This stylish hotel is set amidst tropical gardens and just a few minutes from bustling downtown Key West.
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Hilton Key West Resort & Marina
Hilton Key West Resort & Marina
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Perched on tranquil Stock Island, just a short drive from Key West’s old town, this delightful hotel offers the best of both worlds.
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Isla Bella Resort, Marathon
Isla Bella Resort, Marathon
4 star

The Keys

Set between glistening ocean, sandy beach and swaying palms, this chic yet relaxed oceanside resort is a real gem in the heart of the Keys.
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Hawks Cay Resort, Duck Key
Hawks Cay Resort, Duck Key
4 star

The Keys

Set amongst 60 acres of tropical surroundings on the small, secluded island, Duck Key, this excellent resort is the perfect getaway for the whole family.
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Bakers Cay Resort, Key Largo
Bakers Cay Resort, Key Largo
3 star

The Keys

Surrounded by tropical forest, this beachside resort offers an easily accessible, yet secluded stay.
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View all our hotels in Florida Keys

WHAT TO DO IN THE FLORIDA KEYS

As well as some awe-inspiring sights, the Florida Keys are also home to unforgettable experiences. These provide a unique insight that sightseeing alone simply can’t replace.

One day you might be sailing out into the turquoise waters in search of bottlenose dolphins and the next learning about Key West’s past and present on an open air trolley stopping of to enjoy vibrant Mallory Square and Flagler’s Railroad Museum.

Our collection of unmissable experiences will really help bring your Florida Keys holiday to life.
Key West Old Town Trolley Tour
Key West Old Town Trolley Tour
Attraction Ticket
Departs: Key West

With so much to learn about Key West’s past and present, jump on this open air trolley for a ...

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Key West Food and Culture Tour
Key West Food and Culture Tour
2½ hours
Departs: Key West

Step away from beaten track and experience the real Key West with its diverse culture and cuisine. ...

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