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Florida Keys Holidays

Holidays to Florida Keys are seaside kicks and tropical vibes on pretty coral islands, with nearly everything you want to do on water right at your feet

There’s that exciting peek of wild dolphins swimming alongside your catamaran, shallow-water snorkelling above the coral reef and glass-bottom boat tours looking out on to marine life below. Whether you’re landing by seaplane to settle down in your thatched bungalow, sipping a rum punch on a private beach or a seasoned angler heading to a salt-water lagoon, Florida Keys holidays are all about a classic island escape.

There’s lots of easy breezy fun to be had for kids out on the ocean and plenty of ice-cream stops and in-resort activities along the way. For a splash of romance, think sunset piers and Champagne evening cruises. Spend days counting coconut palms at the tiny key of Islamorada while enjoying peel-and-eat shrimp lunches and catch-of-the day candlelit dinners, and fish by moonlight on the Gulf Stream where even intrepid beginners will come back with a snapper or two.

There’s a kitschy, eccentric side to Key West but also lots of Caribbean-style charm. Sit down for a pint at famed resident Ernest Hemingway’s favourite Sloppy Joes haunt, get out on the water above the USA’s only living coral barrier reef and then slink off grid to a tiny speck of golden beach on Little Palm Island.

We’re ready to whisk you away to Florida's beautiful Keys and offer a carefully curated and trusted collection of the best travel options when it comes to visiting some of the most beautiful islands in the world.

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Florida Keys Hotels

Our recommendations for the best places to stay in Florida Keys

Ocean Key Resort and Spa

Number one for eating and drinking, sunsets and sightseeing.

Bakers Cay Key Largo - Curio Collection by Hilton

Baker's Cay Resort is set on a small, private beach on a quiet stretch of famous Key Largo, makin...

Cheeca Lodge & Spa Islamorada

Nestled in 27-acres of landscaped gardens, Cheeca Lodge and Spa offers a taste of the Caribbean i...

Isla Bella Beach Resort, Marathon

Nestled amidst 24 acres of tropical gardens, this tranquil oasis brings an extra dose of luxury t...

Playa Largo Resort & Spa, Autograph by Marriott

Breathtaking Florida Bay views pair with fabulous dining options and watersports galore at the he...

The Perry Hotel Key West

This award-winning hotel’s peaceful home on Stock Island keeps it removed from the rowdiest Key W...

Hyatt Centric Key West Resort & Spa

Right on the pulse of Key West’s colourful historic district, an area chock-full of sights, shops...

The Reach, A Waldorf Astoria Resort

Old Town charm meets refined luxury at this elegant hotel.

Holidays in Florida Keys

  • Florida Keys
  • 4 Star

Number one for eating and drinking, sunsets and sightseeing.
  • Florida Keys
  • 4 Star

Baker's Cay Resort is set on a small, private beach on a quiet stretch of famous Key Largo, making it an ideal stopover on your journey along the spectacular Overseas Highway.
  • Florida Keys
  • 5 Star

Nestled in 27-acres of landscaped gardens, Cheeca Lodge and Spa offers a taste of the Caribbean in the Florida Keys.
  • Florida Keys

Nestled amidst 24 acres of tropical gardens, this tranquil oasis brings an extra dose of luxury to the Sunshine State.
  • Florida Keys
  • 4 Star

Breathtaking Florida Bay views pair with fabulous dining options and watersports galore at the heart of Key Largo.
  • Florida Keys
  • 4 Star

This award-winning hotel’s peaceful home on Stock Island keeps it removed from the rowdiest Key West crowds.
  • Florida Keys
  • 4 Star

Right on the pulse of Key West’s colourful historic district, an area chock-full of sights, shops and general good times, this resort is a haven for poolside lounging, watersports and taking in epic sunsets with a cocktail in hand.
  • Florida Keys
  • 4 Star

Old Town charm meets refined luxury at this elegant hotel.

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Tour
  • North and Central America

Best of Florida Road Trip

Start with a whirlwind time in Orlando, then leave the frivolities behind as you search out Florida’s finest East Coast beaches and the endlessly fascinating Everglades before arriving in Miami. Sip Cuban coffee and mojitos and soak up the beach scene of this scintillating city before driving one of the world’s most famous routes — the 42 bridges that make up the incredible Overseas Highway all the way to the USA’s most southerly point at Key West.

Tour
  • North and Central America

Key West Road Trip

This road trip blends scenic drives with downtime in tropical surroundings. The views you’ll get from the Overseas Highway are spectacular. And when you arrive in the Florida Keys, you can turn off the engine and tune into laid-back vibes and sultry sunsets.

Tour
  • North and Central America

Tropical Horizons

Miami’s South Beach and Art Deco eye candy is just the beginning of this diverse and decadent city. After getting to know your favourite spots, take a memorable trip across the Overseas Highway – a road and bridges linking the Florida Keys. Eventually, you’ll reach Key West at the southernmost point of the USA. This little Key may be small compared to Miami, but it’s bubbling with personality, nightlife, and tropical beauty.

Key West Old Town Trolley Tour

The island of Key West is full of fun and exciting things to do and see. Explore Key West in the most authentic way aboard an Old Town Trolley that circles the entire island. From the Southernmost Point to the quaint streets of Old Town, this tour has 12 different stops for you to explore all the major areas and attractions, with unlimited re-boarding along the 90-minute route.

See Key West's first tourist attraction, the Key West Aquarium, which was also the world's first open air aquarium. Moving on to Harry Truman’s Little White House which is the state of Florida’s only presidential suite with a rich history spanning back to 1912. The Oldest House Museum is also nearby; it's one of the many beautifully restored homes that are open to the public in Key West dating back to 1829. Stop four covers the famous Duvel Street which has historic significance with St Paul’s Church and the San Carlos Theater. However, it’s probably most famous for being home to nighttime hotspots like Sloppy Joe’s Bar and Jimmy Buffet's Margaritaville. Alight at stop five and see the Ernest Hemingway House Museum where he's rumoured to have written A Farewell to Arms - and don't forget to look for the six- or seven-toed cats! The next few stops provide some contrast; check out the Civil War-era East Martello Fort and Museum and relax on the white sand of Smather’s Beach. Saving the best till last with Stop 10 being at the monument that marks the southernmost point in the US, just 90 miles from Cuba. The tour doesn’t have to end there – you could head back to the Old Town to cool off with a drink and savour Key West with its shops, cafés and galleries. Make sure to stay in Mallory Square for an unmissable sunset.

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Florida Keys Weather

Mar - Jun, Oct - Dec

January
41 mm
February
33 mm
March
30 mm
April
42 mm
May
63 mm
June
109 mm
July
70 mm
August
112 mm
September
145 mm
October
121 mm
November
39 mm
December
38 mm




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