Where to Stay in the Florida Keys

Key West packs more personality per square mile than anywhere else in Florida. Old Town is where you want to be: Duval Street is ground zero for bars and restaurants, while quieter blocks like Olivia, Fleming, and William Street host guesthouses with porches and ceiling fans. The Southernmost Point marker on Whitehead Street is a 10-minute walk from most Old Town hotels. Mallory Square draws the sunset crowd every night. Hemingway's house sits at 907 Whitehead Street. Traffic is brutal in season. Park once and walk everywhere. The heat makes every block feel longer than it looks on a map. Expect to pay a premium for being this far south.

Best for

Nightlife lovershistory buffscouplessolo travelers who want energy and walkability

Walk times

Duval Street to Mallory Square 8 min
Old Town to Southernmost Point marker 12 min
Duval Street to Hemingway Home on Whitehead 10 min

Skip if: You need a quiet beach retreat, you are traveling with young children, or you hate crowds during January through April high season

Local tip: Stay on Simonton Street or Fleming Street for Old Town walkability without the 2am noise from Duval. Request an interior courtyard-facing room at any guesthouse and you will sleep much better.

Compare prices across providers

Prices shown for 1 room, 2 adults. Click to see current availability.

$146per night

Islamorada

Fishing capital, sunset bars, and the best stone crab in the Keys

Mid-range $140-$700/night

Islamorada runs from Mile Marker 74 to Mile Marker 90 and calls itself the Sport Fishing Capital of the World without much argument. Robbie's Marina at MM 77.5 is where locals feed tarpon off the dock every single morning. The Lorelei Restaurant at MM 82 on the Overseas Highway is the go-to sunset spot with live music. Cheeca Lodge is the flagship resort at MM 82, sitting on a private beach. Theater of the Sea at MM 84.7 offers dolphin encounters. Hotels here spread along the Overseas Highway with bay or ocean views. A car is essential for everything including groceries, gas, and most restaurants.

Best for

Anglerscouples wanting a quieter resort feelseafood loversbackcountry kayakers

Walk times

Cheeca Lodge to Robbie's Marina: -drive, not walkable 5 min
Most hotels to Overseas Highway restaurants: 5 to 10 min
Lorelei Restaurant to Islamorada Fish Company 3 min

Skip if: You want walkable nightlife, you are skipping a rental car, or you want a proper wide swimming beach

Local tip: Book bay-side for calmer water and better sunsets. Ocean-side gets more wind and chop. Hotel listings are vague about which water they actually front so ask directly before booking.

Compare prices across providers

Prices shown for 1 room, 2 adults. Click to see current availability.

$157per night

Marathon

Affordable base camp at the midpoint of the Keys

Mid-range $100-$450/night

Marathon sits at Mile Marker 50, literally the geographic center of the Keys, and that location is its biggest selling point. You can day-trip to Key West 1.5 hours south or Key Largo 1 hour north without paying for hotels in either place. The Seven Mile Bridge begins at MM 47 and is one of the most scenic drives in the country. Dolphin Research Center is at MM 59. Sombrero Beach at the end of Sombrero Beach Road is a free public sand beach, rare in the Keys. Boot Key Harbor at MM 48 is a major boating hub. Hotels and motels here cost noticeably less than Islamorada or Key West for comparable quality.

Best for

Familiesbudget-conscious travelersroad-trippers splitting the Keysdivers targeting Sombrero Reef

Walk times

Hotels near MM to Overseas Highway restaurants: 5 to 15-drive 50 min
Sombrero Beach Road hotels to the beach 10 min
Marathon city center to start of Seven Mile Bridge: -drive 5 min

Skip if: You want a walkable town with restaurants and bars within strolling distance of your hotel

Local tip: Stop at Keys Fisheries at MM 49 on the bay side for smoked fish dip and lobster bisque in season. It is a working dockside operation with outdoor seating, not a tourist trap.

Compare prices across providers

Prices shown for 1 room, 2 adults. Click to see current availability.

$112per night

Key Largo

The gateway key for divers and a quick escape from Miami

Mid-range $90-$420/night

Key Largo is the first island coming south on US-1 from Miami and the best base for underwater activity in the entire chain. John Pennekamp Coral Reef State Park at MM 102.5 protects the only living coral barrier reef in the continental United States. Dive operators line the Overseas Highway between MM 90 and MM 104. The African Queen, the actual boat from the 1951 Humphrey Bogart film, docks at MM 100 at the Holiday Inn marina. Most hotels cluster between MM 90 and MM 104. The area is spread out and fully car-dependent but sits 50 miles closer to Miami than Key West, making it the easiest Keys stop for a weekend trip.

Best for

Diverssnorkelersfamilies wanting cheaper rates with easy Miami airport access

Walk times

MM area hotels to John Pennekamp State Park entrance: 5-drive 100 min
Most hotels to nearest dive shop: under -drive 10 min
Card Sound Road junction to MM hotels: 15-drive 100 min

Skip if: You want the full Florida Keys atmosphere. Key Largo feels suburban compared to Key West or Islamorada and has almost no town center to speak of.

Local tip: Stay bay-side near MM 97 to 100 for calmer water and better sunset views. Ocean-side hotels get reef access faster for divers but the wind makes waterfront dining less pleasant.

Compare prices across providers

Prices shown for 1 room, 2 adults. Click to see current availability.

$101per night