Where to Stay in the Florida Keys

Key West packs more into a square mile than anywhere else in the Keys. Old Town runs along Duval Street from the waterfront to Whitehead Street, and that is where most visitors end up. Walk to the Hemingway Home on Whitehead, catch sunset at Mallory Square, then eat conch fritters at Half Shell Raw Bar on Margaret Street. Hotels range from boutique guesthouses on Fleming Street to the Waldorf Astoria Casa Marina on Reynolds Street, which opened in 1921. Duval Street bars stay open until 4am. For quiet, look for properties on the south side near South Beach.

Best for

First-timersnightlife seekershistory buffscouples

Walk times

Mallory Square sunset 8 min
Duval Street 5 min
Key West International Airport 12 min

Skip if: You want peace and quiet or are traveling with young kids

Local tip: Stay south of Eaton Street to get Old Town charm without the Duval Street bar noise at 2am.

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$202per night

Islamorada

Sportfishing capital with upscale resorts and serious sunsets

Luxury $220-$750/night

Islamorada sits between mile markers 73 and 90 and bills itself as the sportfishing capital of the world. The guides at Bud n Mary's Marina on U.S. 1 have been putting clients on permit, tarpon, and bonefish for over 75 years. Cheeca Lodge near MM 82 draws visitors who never touch a fishing rod and has 27 acres of Atlantic beachfront. Anne's Beach off County Road 664 is free and good for families. Marker 88 on the bay side has been a local institution for decades. Fewer bars than Key West, better fishing access, and calmer water on the bay side.

Best for

Anglerscouples seeking upscale resortssnorkelersdivers

Walk times

Cheeca Lodge beach to Anne's Beach 10 min
Bud n Mary's Marina to Marker 88 restaurant 5 min
Islamorada to Key West: 85 miles, about 95 min

Skip if: You want walkability or nightlife beyond a few waterfront bars

Local tip: Book the bay-side rooms at any resort. Sunrise over Florida Bay is better than sunset from most spots here.

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$246per night

Marathon and Duck Key

Family-friendly middle ground with the best bridge view in Florida

Mid-range $150-$500/night

Marathon is the most practical base in the Keys if you are traveling with kids. The city sits around mile marker 50, next to the Seven Mile Bridge, and the view from that bridge at sunrise is one of the best in Florida. Sombrero Beach on Sombrero Road has calm Atlantic water and free parking. The Dolphin Research Center near MM 59 has real educational value. Duck Key is where Hawk's Cay Resort takes up most of the island, with a marina, five pools, and a private beach. Grocery stores, pharmacies, and a hospital make Marathon more livable than the lower Keys.

Best for

Familiesroad-tripperspeople exploring the full Keyskayakers

Walk times

Sombrero Beach to downtown Marathon 10 min
Hawk's Cay Resort to Seven Mile Bridge viewpoint 8 min
Marathon to Key West: 50 miles, about 55 min

Skip if: You want to walk to bars and restaurants from your room

Local tip: Get up at 6am and drive to the old Seven Mile Bridge walking path. No tourists, perfect light, frigate birds overhead.

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$168per night

Key Largo

Diving and snorkeling hub closest to Miami

Mid-range $120-$400/night

Key Largo starts at mile marker 112 and is where you come to dive John Pennekamp Coral Reef State Park, the first undersea park in the U.S. The park entrance is at MM 102.5 on U.S. 1, with glass-bottom boat tours leaving daily from the marina. The original African Queen steamboat docks at the Holiday Inn Resort Key Largo on U.S. 1. Hotels skew toward dive resorts and fishing lodges rather than boutique properties. Snapper's Waterfront Restaurant on Overseas Highway has the best local seafood scene. It is 60 miles from Miami, and Sunday afternoon traffic heading north is brutal.

Best for

Diverssnorkelersbudget travelersweekend visitors from Miami

Walk times

John Pennekamp park entrance to most Key Largo hotels: 5 to 15 min
African Queen dock to Snapper's restaurant 6 min
Key Largo to Miami International Airport: 60 miles, 75 to 120 min

Skip if: You want Key West nightlife or do not plan to get in the water

Local tip: If you are arriving Friday night from Miami, leave by 2pm or you will sit in the U.S. 1 crawl for two hours.

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$134per night