Aerial view of a palm-covered island in the turquoise water of the Florida Keys
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9 nights · Miami, United States → Key West, United States · Car

Miami and The Florida Keys

The Overseas Highway runs to Key West, past pastel-hued houses and Islamorada’s marine adventures – nine nights from Miami’s Art Deco streets to the Keys’ famous sunsets.

From£1,256pp
Duration9 days
StyleSelf-guided
Best suited toDrivers who want the road to be the holiday
Find out more
An independent Stradora pick. Details from the operator's published information, last checked 28 Oct 2026. Stradora DiscoveryChosen independently by our editors because we think it's worth the drive. We're not partnered with this operator: dates, prices and booking are handled by them, and we last checked their published details on 28 Oct 2026.
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9 nights through United States

Nine nights from Miami down the Keys, self-guided, along the Overseas Highway, with the flights included.

The Overseas Highway is the trip. It runs a hundred and thirteen miles out into the sea on more than forty bridges, built on the bed of Flagler’s railway after a hurricane destroyed it in 1935, with water on both sides for most of the way.

Miami opens it for three nights, with Ocean Drive and the Art Deco district in South Beach, the Cuban coffee houses of Little Havana and the Design District. Key Largo follows for two, where the diving and snorkelling start and the first undersea park in the United States sits offshore. Islamorada comes next for two, with Marathon and the Seven Mile Bridge beyond it, then Key West for two at the end: pastel timber houses, a literary history out of proportion to its size, and a nightly ritual of watching the sun go down from Mallory Square.

Return flights to Miami, a checked bag each way, nine days of fully inclusive car hire in a four-door automatic from Miami airport and nine nights’ room-only accommodation at the named hotels are included; fuel, meals, attraction admissions and resort fees of 326 euros, payable locally, are not. The price shown is per person sharing. December to April is the season, since the summer is humid and the hurricane season runs from June to November. Ten days arranged with four bases and short drives between them is a holiday rather than a road trip, and the resort fees are the detail to budget for rather than discover on arrival.

Style
Self-guided
Duration
A week or so (7-10 nights)
Region
North America
Vehicle provision
Vehicle provided
Departures
September
Starts/ends
Miami, United States → Key West, United States
Accommodation
Hotels
Suitable cars
Drivers who want the road to be the holiday
Vehicle
Car
Price basis
Per person (sharing)
Run by
Independent specialist operator

What's included

  • Return flights to Miami
  • 1 checked bag per person roundtrip
  • 9 days fully inclusive car hire (4-door automatic A/C)
  • Miami International Airport pick-up and drop-off
  • 9 nights' room-only accommodation at named hotels.

Not included

  • Fuel
  • meals
  • total resort fees of EUR326 (paid locally)
  • attraction admission.

Ready to drive it?

9 days, from £1,256pp

Independent Stradora pick
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