Best Overseas Highway hotels

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Unfolding like a hallucination, the Overseas Highway is a 113-mile long dream through the Florida Keys. The tropical views are hard to miss, yet it’s a drive that takes time to be fully appreciated. But where to stay along the Overseas Highway for the best experience?

There are 5 main areas along the way: Key Largo, Islamorada, Marathon, Lower Keys and Key West. Although each area is unique, they all offer that Caribbean-feeling, palm tree-dotted, sun-drenched setting like made for recharging vacations.

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Make acquaintance with the Overseas Highway

The Overseas Highway extends for 113 miles (182 km) from mainland Florida to Key West. It takes you through Key Largo, Islamorada, Marathon and Lower Keys before you — at the end of the road — arrive in Key West.

Along every stretch of the Overseas Highway you find appealing hotels. Framed by crystal clear waters and with a Caribbean vibe present, it’s hard not to like what you see.

Want a teaser? Then have a look at the mouth-watering Islander Resort and Cheeca Lodge & Spa right away.

To make this guide to the best Overseas Highway hotels as easy as possible for you to follow, every place to stay is marked with a mile marker. They start high and conclude with Mile Marker Zero in Key West.

Well, that’s it folks. Are you ready to have a look at the best Overseas Highway hotels?

Swimming pool framed by palm trees at Cheeca Lodge & Spa, Islamorada
Cheeca Lodge & Spa — a top place to stay along the Overseas Highway.

1. Embrace the Atlantic Bay Resort

  • Mile Marker: 92.5
  • Area: Key Largo

Upon arriving in Florida Keys, possibly after an afternoon at John Pennekamp, Atlantic Bay Resort makes up a first great Overseas Highway hotel. Welcome to a tropical oasis situated at mile marker 92.5.

Featuring a private beach and lovely pool area, Atlantic Bay Resort is just the right spot for lazy days. But if you want to be active, take advantage of additional amenities including kayaks and paddleboards.

2. Bed down at Coconut Palm Inn

  • Mile Marker: 92
  • Area: Key Largo

Not far from the Atlantic Bay Resort, the waterfront of Coconut Palm Inn enchants visitors. And, what’s there not to like about 450 soft feet (137 m) of exclusive beachfront?

Lounge on the sand or by the gorgeous pool as the sun sinks lower and lower over the Florida Bay. Facing west, Coconut Palm Inn is the place to be around sunset — don’t miss it!

Overseas Highway sign in Florida Keys
Key Largo is the first area along the Overseas Highway.

3. Enjoy the Islander Resort

  • Mile Marker: 82.1
  • Area: Islamorada

When navigating Islamorada, you can easily feel overwhelmed by the selection of stunning hotels. Here, halfway between Miami and Key West, they line up one after another.

Still the Islander Resort, offering the definition of a carefree escape, manages to stand out a bit extra.

First soak up the sun in style on the resort’s lovely beach. Then, before the Florida Keys sun gets the better of you, have a drink by the pool or challenge your company (or any fellow guest) in a game of shuffleboard.

4. Check in at Cheeca Lodge & Spa

  • Mile Marker: 82
  • Area: Islamorada

Literally a stone’s throw down the road from the Islander Resort, you find Cheeca Lodge & Spa. With an impressive 525 feet (160 m) long fishing pier elegantly shooting out into the Atlantic Ocean, this Overseas Highway hotel creates some headache.

Should you stay at the palm-dotted property to enjoy the eye-popping Caribbean setting? Or should you make full use of the photogenic pier and head out on an adventure on the water? Oh boy, life is really tough sometimes.

White entrance gate to Cheeca Lodge Spa & Resort in Islamorada
Welcome to Cheeca Lodge & Spa.

5. Find a home at Seascape Resort & Marina

  • Mile Marker: 50
  • Area: Marathon

The heart of the Florida Keys, Marathon is positioned halfway between Key Largo and Key West. Here, convenient both for day trips and a relaxed spot for a getaway, Seascape Resort & Marina is a hidden Overseas Highway hotel.

Step into a home away from home — one overlooking the ocean, with a private beach and miniature marina. Seascape Resort & Marina may seem upscale, but it isn’t. Still it has everything you love about the Keys.

6. Unwind at Parmer’s Resort

  • Mile Marker: 28.5
  • Area: Lower Keys

If you’re after activity or an exclusive Overseas Highway hotel, keep reading. The Lower Keys region between Marathon and Key West is quiet, and the Parmer’s resort is a low-key place to stay.

Yet, if you want something off the beaten path and don’t require luxury, Parmer’s Resort may be the perfect match. Spread out over five tranquil acres on Little Torch Key, this is old-school lodging at its best.

7. Recharge at Almond Tree Inn

  • Mile Marker: 0
  • Area: Key West

So where should you stay at the end of the Overseas Highway? How can you best crown the conclusion of such a unique American drive?

For adults, don’t look past Almond Tree Inn. It offers the luxury of a resort yet operates with a passion that you often only find at bed and breakfasts.

Lounge by the swimming pool before you retreat to enjoy the comfy beds — of course with quality bedding. The next morning, wake up recharged and enjoy a complimentary continental breakfast of the highest order.

Final words about the best Overseas Highway hotels

The Florida Keys is an area like no other in the world, and the Overseas Highway showcases an abundance of stunning resorts and quirky attractions. With so much splendor, it’s not always easy to decide how to approach.

But use this guide, and you’ve got the best places to stay along the Overseas Highway sorted out — in north to south order. Now when you know exactly where to bed down, enjoy the unique drive that the Overseas Highway is.

"Spa Island" sign across the backdrop of palm trees and a pool at Cheeca Lodge & Spa in Florida Keys
Treat yourself with a spa treatment at Cheeca Lodge & Spa.

Best Overseas Highway hotels FAQ

Where should I stay when driving the Overseas Highway?

Key Largo, Islamorada, Marathon, Lower Keys and Key West are all beautiful options for where to stay when driving the Overseas Highway. If time allows, try more than one hotel along the way. But if you just have time for one stay, be strategic and break the drive up with an overnighter in either Islamorada, see the Islander Resort and Cheeca Lodge, or Marathon, home to Seascape Resort.

How many overnight stops do you need for the Overseas Highway?

For the best experience, the Overseas Highway should be driven over multiple days. Therefore stay at least one night, but preferably more, as you work your way south towards Key West. At road’s end, all the things to do in Key West motivate a longer stay.

Which are the best Overseas Highway hotels for nightlife?

You find the Florida Keys’ biggest nightlife scene — by a margin — in Key West’s Old Town. Here you can hit both a wide range of watering holes, such as the legendary Sloppy Joe’s, and nightclubs. In comparison, although there are laid-back bars scattered across the Keys, every other Overseas Highway area is quiet.

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