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Bakers Cay Resort Key Largo Curio Collection by H, Key Largo

Where to stay guide

Where to stay in the Florida Keys: the best islands and hotels

Updated 7 October 2026 · 4 areas · 16 hotels picked

Pictured: Bakers Cay Resort Key Largo Curio Collection by H

The Florida Keys are a road trip disguised as a beach holiday. One highway, the Overseas Highway, hops from island to island for more than a hundred miles, with the Atlantic on one side, the Gulf of Mexico on the other and a pelican on most lamp posts. The water is the point here: reef, mangrove and flats in a dozen shades of blue-green, rather than long sandy beaches.

Each stretch has its own temperament, so choose by mood. Key Largo, nearest Miami, is for divers and snorkellers. Islamorada is for fishing and quiet luxury. Marathon, halfway down, is the family all-rounder by the Seven Mile Bridge. And Key West, at the very end of the road, is the party: a tiny, handsome old town that takes sunset more seriously than almost anything else.

The short answer

Florida Keys areas at a glance

Key LargoDiving, Short trips, CouplesThe first key and the diving capital, an hour or so from Miami.Hotels: 23
IslamoradaCouples, Fishing, LuxuryBarefoot, well-heeled and obsessed with fishing.Hotels: 18
MarathonFamilies, Boating, Halfway stopThe family-friendly middle, at the foot of the Seven Mile Bridge.Hotels: 21
Key WestNightlife, First-timers, HistoryThe end of the road: gingerbread houses, roosters and a standing ovation for the sunset.Hotels: 75

Key Largo

Bakers Cay Resort Key Largo Curio Collection by H, Key Largo
Playa Largo Resort & Spa, Autograph Collection, Key Largo
Reefhouse Resort and Marina, Key Largo
Pictured: Bakers Cay Resort Key Largo Curio Collection by H · Playa Largo Resort & Spa, Autograph Collection · Reefhouse Resort and Marina
  • Diving
  • Short trips
  • Couples
The first key and the diving capital, an hour or so from Miami.

Key Largo is where the mainland lets go. It is the first and largest of the keys, about an hour's drive from Miami, and most people come for what's under the surface: John Pennekamp Coral Reef State Park protects a long sweep of living reef just offshore, and dive and snorkel boats leave all day.

On land it is low-key, a long green island with resorts hidden down side roads on the calm Gulf side. The best of them are spread over acres of hardwood forest and waterfront, with their own marinas, small private beaches, spas and hammocks strung between the palms. Sunsets over the bay are the main evening event, and nobody seems to mind.

Hotels to look at in Key Largo

Islamorada

Cheeca Lodge & Spa, Islamorada
Three Waters Resort And Marina, Islamorada, Islamorada
Amara Cay Resort, Islamorada
Pictured: Cheeca Lodge & Spa · Three Waters Resort And Marina, Islamorada · Amara Cay Resort
  • Couples
  • Fishing
  • Luxury
Barefoot, well-heeled and obsessed with fishing.

Islamorada, a string of small islands just over an hour south of Miami, bills itself as the sport-fishing capital of the world, and the marinas full of charter boats back that up. Even if you never pick up a rod, you get the benefit: seafood straight off the dock, and the Everglades backcountry on one side with the coral reef on the other.

This is also where the Keys do grown-up luxury. A handful of oceanfront resorts have private beaches, several pools and spas, including one of the most celebrated hotels in the islands. Smaller beachfront places have their own marinas, kayaks and villas. It's quiet after dark, which is rather the idea.

Hotels to look at in Islamorada

Marathon

Isla Bella Beach Resort, Marathon
Faro Blanco Resort Marathon CurioCollection Hilton, Marathon
Tranquility Bay Beach House Resort, Marathon
Pictured: Isla Bella Beach Resort · Faro Blanco Resort Marathon CurioCollection Hilton · Tranquility Bay Beach House Resort
  • Families
  • Boating
  • Halfway stop
The family-friendly middle, at the foot of the Seven Mile Bridge.

Marathon sits halfway down the chain, which makes it the natural base if you want to see both ends. It is a working town with a fishing-resort past, a marina with a landmark lighthouse and, at its western edge, the start of the Seven Mile Bridge, the most famous stretch of the whole drive.

Families do well here. Resorts tend to come with two or three pools, private beaches, bikes to borrow and tiki bars for the adults, and there's a beach-house style resort with spa treatments for when the children are finally asleep. Key West is close enough for a day trip, and far enough that you'll sleep.

Hotels to look at in Marathon

Key West

Casa Marina Key West, Curio Collection by Hilton, Key West
Ocean Key Resort & Spa, Key West
La Concha Key West Autograph Collection, Key West
Pictured: Casa Marina Key West, Curio Collection by Hilton · Ocean Key Resort & Spa · La Concha Key West Autograph Collection
  • Nightlife
  • First-timers
  • History
The end of the road: gingerbread houses, roosters and a standing ovation for the sunset.

Key West is closer to Havana than to Miami, and it behaves accordingly. Old Town is a few square miles of wooden houses with wraparound porches, bougainvillea, free-roaming roosters and bars that Hemingway would still recognise. Duval Street runs through the middle of it, loud and cheerful from lunchtime, and every evening a crowd gathers at Mallory Square to applaud the sun into the Gulf.

Stay in Old Town if you can: you can walk or cycle everywhere and never think about parking. The choice runs from a grand, historic beachfront resort on the Atlantic side to waterfront hotels by the harbour and garden bungalows on quiet lanes. Resorts on neighbouring Stock Island have more space and more pools, with shuttles to Duval Street.

Hotels to look at in Key West

One base or two?

If you have a week, split it: a few nights in Key Largo, Islamorada or Marathon for the water, then finish in Key West. With only two or three nights, pick one. Go to the Upper Keys for snorkelling and peace, or straight to Key West for atmosphere, and accept that you'll spend a good part of a day on the road each way.

Getting there

Most visitors fly into Miami and drive. Key Largo is about an hour away and Islamorada a little more; Key West, at the far end of the Overseas Highway, is three and a half to four hours without stops. Key West also has its own small airport if you would rather skip the drive, though the drive is half the fun.

Sorted where to stay? Now plan the days. Read our guide: The best things to do in the Florida Keys →

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Questions about where to stay in Florida Keys

Which is the best key to stay on in the Florida Keys?
For a first visit, Key West: it has the most to see and do, and the old town is walkable. For snorkelling and diving, stay in Key Largo. For a quiet, upmarket break, choose Islamorada, and for families or a central base, Marathon.
Is it better to stay in Key West or Key Largo?
They are very different. Key West is lively and historic, with bars, restaurants and nightlife, but it is a long drive from Miami. Key Largo is quiet, much closer to the mainland and better for the coral reef. Many visitors do a few nights in each.
Where should families stay in the Florida Keys?
Marathon is the easiest choice for families, with resort pools, calm private beaches and a central position for day trips in both directions. Key Largo and Islamorada also have family-friendly waterfront resorts.
Do the Florida Keys have good beaches?
The Keys are coral islands, so natural sandy beaches are small and few. Many resorts in Islamorada, Marathon and Key Largo have their own private beaches, and the real draw is the clear, shallow water for snorkelling, kayaking and boating.