Best Overseas Highway hotels

  • Post last modified:January 26, 2023
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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. So which are the best Overseas Highway hotels to stay at?

In this guide, you find not only the best places to stay along the Overseas Highway. It also includes all the best attractions, and their locations, in relation to those stunning Overseas Highway hotels.

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Guide to Overseas Highway lodging

The Overseas Highway extends for 113 miles 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.

Do you 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 and attraction 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 and attractions?

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

1. Splash in John Pennekamp State Park

  • Mile Marker: 102.5
  • Area: Key Largo

The Florida Keys are famous for its diving and snorkeling, so it’s no surprise that you find an exceptional stop for that already at mile marker 102.5. Are you ready to plunge into the inviting water of the Florida Keys?

Encompassing 70 nautical square miles, John Pennekamp State Park is so big that there always are new corals and more marine wildlife to admire. Underwater, the curious creatures of the sea greet you to their lovely world.

But you don’t have to go below the surface to explore John Pennekamp. Other popular activities in John Pennekamp State Park include kayaking, canoeing and exploring by glass-bottom boat.

Visit: John Pennekamp Coral Reef State Park

2. 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. Situated at mile marker 92.5, welcome to a tropical oasis.

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.

Stay: Atlantic Bay Resort

3. 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. 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, a sunset here is the ultimate way to end the first day of your Keys vacation.

Stay: Coconut Palm Inn

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

4. See dolphins at Theatre of the Sea

  • Mile Marker: 84.5
  • Area: Islamorada

Floating south of mainland Florida’s southern tip, the Florida Keys’ waters are just filled with marine life. The Theater of the Sea, a marine mammal park founded in 1946, hosts and shows many of these species up close.

Lessening the gap between Florida’s animal kingdom and you, the Theatre of the Sea presents an array of animals — many of them who have been rescued and deemed non-releasable by agencies — such as dolphins, sharks, turtles alligators, fish and birds.

Visit: Theatre of the Sea

5. Learn at History of Diving Museum

  • Mile Marker: 83
  • Area: Islamorada

The Florida Keys, boasting warm and crystal-clear waters, is a mecca for divers. To add some background to the diving experience, stop by at the History of Diving Museum.

Preserving and showcasing — with a Florida Keys focus — the History of Diving Museum tells an engaging story spanning from early days of free diving to scuba diving.

Learn the facts every diver should know, be amazed by jaw-dropping diving equipment from the past and hold a silver bar, which actually have been recovered from a shipwreck (it’s heavy), in your hands. As you tour the museum, a scavenger hunt tests your observational power.

Visit: History of Diving Museum

6. Enjoy the Islander Resort

  • Mile Marker: 82.1
  • Area: Islamorada

When navigating Islamorada, you can easily feel overwhelmed by the selection of stunning Overseas Highway 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 in a game of shuffleboard.

Stay: Islander Resort

7. 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 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 its 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.

Stay: Cheeca Lodge & Spa

White entrance gate to Cheeca Lodge Spa & Resort in Islamorada — a top Overseas Highway resort
Welcome to Cheeca Lodge & Spa.

8. Paddle to Indian Key

  • Mile Marker: 78.5
  • Area: Islamorada

No matter how great the Overseas Highway is, it can’t take you to every island in the Florida Keys. One such island, located within sight of the Overseas Highway, is Indian Key.

You certainly wouldn’t think so when you see Indian Key from a distance, but this tiny island became the first county seat for Dade County in 1836. Then it was a hub for the at the time booming shipwrecking business.

If you kayak the half a mile over to Indian Key, you find remnants of buildings from the old shipwrecking community. The history is a fascinating ingredient, but many just come to swim or for the adventure.

Visit: Indian Key State Park

Do you need a kayak? Don’t worry, you can rent kayaks at the nearby Robbie’s Marina.

9. Hang out at Robbie’s

  • Mile Marker: 77.5
  • Area: Islamorada

Robbie’s likes to mention that it has been voted the number one place to visit in the Keys. This is both an Islamorada and Florida Keys hub.

Masses of tarpon, often over 100, wait at Robbie’s dock for food. When a tarpon spot fish in your hand, it prominently rises up from the water to grab it from you.

Although the tarpon feeding is Robbie’s number one show, other reasons to visit are the Hungry Tarpon Restaurant and Thirsty Tarpon Bar. If you want a memory with you home — check out Robbie’s open-air shops.

Visit: Robbie’s

Tip: Beware of pelicans at the feeding. Those birds want that fish too.

10. 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 might seem upscale, but it isn’t. Still it has everything you love about the Keys.

Stay: Seascape Resort & Marina

11. Relax on Sombrero Beach

  • Mile Marker: 50
  • Area: Marathon

It doesn’t have to be complicated: Swaying palm-trees, crystal-clear water and soft sand takes an Overseas Highway stop a long way. Like a Florida Keys dream, Sombrero Beach in Marathon shows that brilliantly.

So unfold a towel, sit down and let Sombrero Beach do its magic — while a gentle breeze blows through your hair. When you’re ready, get some sand between your toes and plunge into the inviting water.

Visit: Sombrero Beach

12. Marvel at Florida Keys Turtle Hospital

  • Mile Marker: 48.5
  • Area: Marathon

The Florida Keys region is inhabited by five turtle species. To learn about and get to know those shell-protected reptiles, there’s no better spot than the Florida Keys Turtle Hospital.

First watch an educational presentation about turtles. Then tour the facilities where injured turtles recover — with the ambition to return to their natural habitat. Top if all off with feeding of permanent residents.

Do you need more motivation? The money you spend here goes towards future rehabilitation of turtles.

Visit: Turtle Hospital

For the cause: Check out the Turtle Hospital’s gift shop.

The turtle hospital in Marathon
Be amazed at Marathon’s Turtle Hospital.

13. Photograph Bahia Honda Beach

  • Mile Marker: 37
  • Area: Lower Keys

Although there are several pretty beaches in the Keys, Bahia Honda Beach overshadows all other when it comes to picturesqueness. Overlooking the historic Bahia Honda Rail Bridge, its views are second to none.

Get that mandatory picture for Instagram — likes will flow. Then plunge into the warm blue water and soak up the iconic Florida Keys view from another perspective.

Visit: Bahia Honda Beach

14. Spot deer at National Key Deer Refuge

  • Mile Marker: 30.5
  • Area: Lower Keys

“Cute”, “tiny” and “where is it” are common reactions in the National Key Deer Refuge. Here the adorable key deer, North America’s smallest white-tailed deer subspecies, lives.

These animals, unique to the Lower Keys, are really small. Bucks reach 30 inches (76 cm) and does 26 inches (66 cm) at the shoulders.

For the best experience, get out of your car and hike the trails in the refuge. To increase the chances of wildlife encounters even further, visit early or late in the day when the key deer is as most active.

Visit: National Key Deer Refuge

15. Unwind at Parmer’s Resort

  • Mile Marker: 28.5
  • Area: Lower Keys

If you’re after activity or an upscale 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 might be the perfect match. Spread out over five tranquil acres on Little Torch Key, this is old-school Overseas Highway lodging at its best.

Stay: Parmer’s Resort

16. Enter Hemingway’s world

  • Mile Marker: 0
  • Area: Key West

At road’s end, after 113 miles of stunning Overseas Highway hotels and sights, the show continues in Key West. It’s hard not to fall for the southernmost island city, and one who certainly did so was Ernest Hemingway.

Hemingway, celebrated American writer, spent several of his most productive years in Key West. While he lived in Key West in the 1930s, he among other novels wrote Green Hills of Africa and Death in the Afternoon.

Today, you can visit Hemingway’s old home and workplace on Whitehead Street in Key West. Come to see how he lived, hear entertaining stories about his life and cuddle with descendants of his cats, many of which have six toes.

Ernest Hemingway Key West bed and cat
Step into Hemingway’s Key West home.

17. Celebrate 5 PM on Duval Street

  • Mile Marker: 0
  • Area: Key West

Few places, if any, live by the widely used “It’s 5 PM somewhere” motto like Key West. Duval Street, the main drag in Key West, is a hub where something fun always is going on.

Explore sights, such as the Butterfly Garden, browse shops, full of quirky trinkets, have a refreshing beverage, Key West is almost always hot, and then have another one — It’s 5 PM somewhere.

18. 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 drive?

For adults, don’t look past Almond Tree Inn. It’s an inn that offers the luxury of a resort yet is operated with a love 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.

Stay: Almond Tree Inn

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 both the best places to stay and the best sights along the Overseas Highway sorted out — in north to south order. All that remains, now when you know exactly where to stop, is for you is to enjoy the unique drive that the Overseas Highway is.

Best Overseas Highway hotels FAQ

Here you find the answers to some frequently asked questions about where to stay along the Overseas Highway.

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 Overseas Highway 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 find 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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