Florida Keys Holidays
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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.
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
USA
Fly Drive Holiday
11 days / 10 nights
11 days / 10 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.
Luxury Florida
USA
Fly Drive Holiday
16 days / 15 nights
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. Soak up the natural flair for sophistication while staying at some of Florida’s most luxurious hotels and let the delights of the Sunshine State whisk you away.
Wild Florida
USA
Fly Drive Holiday
18 days / 17 nights
18 days / 17 nights
Discover Florida’s natural wonders and encounter its enchanting wildlife on this unique adventure. Spot ‘gators in the wilderness of the Everglades, manatees basking in crystal waters and dolphins dancing in the waves as you explore both highlights and hidden gems of the Sunshine State.
Unique & Boutique Florida
USA
Fly Drive Holiday
18 days / 17 nights
18 days / 17 nights
From glamorous tree-lined boulevards to quirky seaside towns, unspoiled islands and little known pockets of history, Florida is full of surprises. Let the delights of the Sunshine State whisk you away while you enjoy the hospitality of its most charismatic hotels.
Wildlife & Waterbabies
USA
Family Holiday
14 days / 13 nights
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. Be guided by the sea breeze, grab your swim gear and relax into island time.
Miami & the Florida Keys
USA
Honeymoon
12 days / 11 nights
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. Coast above warm waters and magical coral reefs, hopping from island to island as you cruise along the spectacular Overseas Highway.
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.
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
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
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
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 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
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
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.
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
The Keys
This charming resort reflects island living with its laidback pace and bags of charm.
Havana Cabana, Key West
The Keys
This stylish hotel is set amidst tropical gardens and just a few minutes from bustling downtown Key West.
Oceans Edge Resort & Marina, Key West
The Keys
Perched on tranquil Stock Island, just a short drive from Key West’s old town, this delightful hotel offers the best of both worlds.
Amara Cay Resort, Islamorada
The Keys
Boasting an enviable waterfront location, this laidback hotel is a wonderful spot from which to explore.
Hawks Cay Resort, Duck Key
The Keys
Set amongst 60 acres in the heart of the Keys, this excellent resort offers a wide selection of activities from dolphin encounters to diving courses.
Reefhouse Resort & Marina
The Keys
Surrounded by tropical gardens and overlooking beautiful Key Largo Bay, this chic resort is the picture-perfect setting to slow down and bask in the laidback charm of the 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.
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
Attraction Ticket
- Experience old town Key West on the famous trolleys
- Hop-on hop-off at any of the 13 stops
Key West Food and Culture Tour
2.5 hours
- Sample mouth watering Key lime pie
- Explore the Keys lesser known areas
- Learn about Key West rich and diverse culture
Tales from the Trail
Top tips and travel inspiration from the Trailfinders team
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