Road Trip · 4–6 days · ~170 miles (Miami to Key West)
Florida Keys Overseas Highway
Miami → Key Largo → Islamorada → Marathon → Key West
A 113-mile highway where the land runs out and the blue takes over.
About This Route
The Overseas Highway is 113 miles of bridges and islands connecting the southern tip of Florida to Key West. It's one of the most distinctive drives in America — aquamarine water on both sides, conch shacks, palm-shaded bars, and a pace that gets slower every mile. Most travelers rush it in a day and regret it. Give yourself four to six days, spread your overnights across three different keys, and treat it like island-hopping by car.
Member rates matter most in Islamorada and Key West, where the hotel inventory is small and the season rates are high. Winter is peak — if you're flexible, shoulder season (May or November) is a better deal.
— Our Travel Editor
The Route
5 stops · book hotels at member rates in each city.
Miami / South Beach
Start with a night in Miami. Art Deco, Cuban food, and South Beach before heading south.
Key Largo
The first key. Dive Pennekamp Coral Reef State Park or just ease into the pace.
Islamorada
Sport fishing capital of the Keys. Sunset dinner at the Lorelei is non-negotiable.
Marathon / Seven Mile Bridge
The middle keys. Turtle Hospital, Bahia Honda State Park, and the most iconic bridge on the drive.
Key West
The finish line. Mallory Square sunset, Hemingway House, Duval Street. Stay two nights.
Hotels to Build Your Route
A curated list of member-rate hotels along every stop on this drive.
How to build your road trip
Book each hotel below through its link to lock in member rates for every night of your trip. One click per stop — no coupon codes, no timing games. Complete your bookings in the order you'll drive the route.
A sustainability-forward oceanfront luxury hotel on Collins Avenue — the ideal launch night before pointing south for the Overseas Highway.
A 14-acre bayfront resort with its own private beach — the most polished place to stay on Key Largo.
Modern oceanfront boutique in the heart of Islamorada's sport-fishing stretch — great pool, great sunsets.
The only resort in the Keys with a private beach on both sides — and a direct view of the Seven Mile Bridge.
Historic conch-style bungalows just off Duval Street — the quintessentially Key West finish for the Overseas Highway.
Travel Editor Tip
The drive is nothing but two-lane highway with one bridge after another — pack snacks and gas up in Homestead before you start.
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Road trip plan courtesy of Hotel Room Discounters
Book every stop at member rates: https://hotelroomdiscounters.com/road-trips/florida-keys
For the full catalog of member-rate hotels, visit hotelroomdiscounters.com.