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.

Florida Keys Hotels

Our recommendations for the best places to stay in Florida Keys

Cheeca Lodge & Spa Islamorada

Perfect for families and couples

Ocean Key Resort and Spa

Number one for eating and drinking, and sunsets and sightseeing, this chic resort’s location righ...

The Reach, A Waldorf Astoria Resort

Comfortable luxury with a private beach

Postcard Inn Beach Resort & Marina

It’s Mid-century motel meets boathouse chic at Postcard Inn. A full-service marina, private beach...

Bakers Cay Key Largo - Curio Collection by Hilton

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

Playa Largo Resort & Spa, Autograph by Marriott

Breathtaking Florida Bay views pair with fabulous dining options and watersports galore at this e...

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 Perry Hotel Key West

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

Holidays in Florida Keys

Hotel

Florida Keys
5 Star

Cheeca Lodge & Spa Islamorada

Perfect for families and couples

Hotel

Florida Keys
4 Star

Ocean Key Resort and Spa

Number one for eating and drinking, and sunsets and sightseeing, this chic resort’s location right by Mallory Square and at the end of Duval Street is first class. It boasts a swoon-worthy seafront vista, vibrant tropical décor and an entertainment-packed pier.

Hotel

Florida Keys
4 Star

The Reach, A Waldorf Astoria Resort

Comfortable luxury with a private beach

Hotel

Florida Keys
3 Star

Postcard Inn Beach Resort & Marina

It’s Mid-century motel meets boathouse chic at Postcard Inn. A full-service marina, private beach, two pools and fun drinking and dining options make this a great stop on the Overseas Highway.

Hotel

Florida Keys
4 Star

Bakers Cay Key Largo - Curio Collection by Hilton

The tranquil 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.

Hotel

Florida Keys
4 Star

Playa Largo Resort & Spa, Autograph by Marriott

Breathtaking Florida Bay views pair with fabulous dining options and watersports galore at this elegant and contemporary beachfront resort.

Hotel

Florida Keys
4 Star

Hyatt Centric Key West Resort & Spa

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

Hotel

Florida Keys
4 Star

The Perry Hotel Key West

This award-winning hotel’s peaceful home on Stock Island keeps it removed from the rowdiest Key West crowds, and the exclusive marina-front setting and marine décor feels very on-brand for the Florida Keys.

Key West Old Town Trolley Tour

In Florida Keys

The island of Key West is full of fun and exciting things to do and see. From the Southernmost Point to the quaint streets of Old Town, this tour takes you to all the major areas and attractions, with unlimited re-boarding. See Key West's first tourist attraction, the Key West Aquarium, which was also the world's first open air aquarium. Cross the street and you'll find yourself back in the 1800s at the Key West Shipwreck Treasure Museum, learning about how Key West became one of the richest cities in the US. 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. Stop by the Ernest Hemingway House Museum where he's rumoured to have written A Farewell to Arms - and don't forget to look for the 6 or 7-toed cats! Marvel at the beautiful species of butterflies in the Key West Butterfly and Nature Conservatory, and wander next door to the Southernmost House Mansion and Museum, known fcal gardens. Cool off with a drink at the famous Sloppy Joe's Bar or Jimmy Buffet's Margaritaville in the Old Town area. But don't leave Key West until you've watched the sunset from Mallory Square.

Florida Keys Weather

Best time to go

Mar - Jun, Oct - Dec

January

21°c

41 mm

February

22°c

33 mm

March

23°c

30 mm

April

24°c

42 mm

May

26°c

63 mm

June

28°c

109 mm

July

28°c

70 mm

August

28°c

112 mm

September

28°c

145 mm

October

27°c

121 mm

November

24°c

39 mm

December

23°c

38 mm

Florida Keys Weather by Month

Sorry, your hotel is no longer available

Please check alternatives

Where do you want to go?

When

Choose dates

{{store.searchDuration}} nights, {{formattedDate}}

Who

From

Class

Occasion

{{item.title}} {{item.body}}
{{item.title}} {{item.body}}

Choose a departure date

Duration

{{store.searchDuration}} nights

Enter rooms & guests

Adults Aged 18 or above

Children Aged 0-17 years

Select child age{{store.passengers[0].childAges.length > 1 ? "s" : ""}}:

Child {{i+1}} Age Age on date of return

+ Add another room

{{airport.text}}

{{flightClass.text}}

{{occasion.text}}

Checking prices & availability

{{term}}, {{formattedDate}} for {{searchDuration}} nights

All ({{destinations.length + products.length + offers.length + inspiration.length}})
Destinations ({{destinations.length}})
Holidays ({{products.length}})
Offers ({{offers.length}})
Inspiration ({{inspiration.length}})