The Keys are one road, and where you sleep decides how much of it you drive each day. The Leonida Keys, where Jason lives, are based on the real Florida Keys, and every place on this site’s Keys pages sits on or just off that road. Pick your base by what you want near you and what you will pay.
The short answer
- Two nights: one in Islamorada or Key Largo, one in Key West, the shape of the Leonida Keys road trip.
- Tight budget: Marathon, or the mainland at Florida City.
- The trailer-matched places close by: Islamorada.
- One base for a week: Marathon.
- Nightlife without a car: Key West’s Old Town.
How the Keys divide up
Addresses are mile markers counting down to zero in Key West; the Overseas Highway guide explains them. The official tourism office splits the chain into Key Largo (MM 108 to 90), Islamorada (MM 90 to 63), Marathon (MM 63 to 40), the Lower Keys (MM 40 to 4) and Key West (MM 4 to 0). Drive times below assume no stops and no weekend traffic.
Key Largo: MM 108 to 90
The closest island to Miami: 58 miles, an hour to an hour and a half. Key West is about 100 miles on, two and a half hours. Along the highway it is dive shops, marinas and strip malls; the good part is behind them. The canal streets are the kind of neighborhood fans have matched to Jason’s canal-side home, the reef is reached from John Pennekamp Coral Reef State Park at MM 102.5, and Card Sound Road and Alabama Jack’s are minutes from the top of the island.
Stay here to dive, after a late landing in Miami, or for the Upper Keys at less than Islamorada charges.
Islamorada: MM 90 to 63
The village proper runs from about MM 90.8 to 72.5; the tourism office’s Islamorada runs on past Long Key to MM 63. This is where the Keys places on this site bunch up: Betsy the giant lobster at Rain Barrel Village, MM 86.7; the bayside tiki bars between MM 77 and 85, which fans have matched to the second trailer’s sunset bar; and the Florida Bay backcountry fans have matched to the mangrove boat runs, with trips from Robbie’s at MM 77.5.
Miami is 76 miles, an hour and a half to two hours; Key West about 80 miles, two hours. It is the priciest of the Upper Keys, and much of what it has comes with a dock, a pool and a resort fee. If the sunset bars are the point, sleep somewhere you can walk home from: the highway after dark is two lanes and patrolled.
Marathon and the Middle Keys: MM 63 to 40
The city runs from Grassy Key (about MM 60) to the foot of the Seven Mile Bridge (MM 47), halfway down the chain. It is the most practical town in the Keys: supermarkets, marinas, chain hotels, and prices that fall a long way outside winter. The Seven Mile Bridge, a clear match for the long bridge in the second trailer, starts at the south end of town, and the old bridge beside it is a free walk, best early in the morning.
Miami is 111 miles, about two and a half hours; Key West about 50 miles, an hour and a quarter. That makes it the best single base for a week, with Islamorada under an hour north, Bahia Honda half an hour south, and Key West close enough for a long day.
Big Pine and the Lower Keys: MM 40 to 4
South of the bridge the Keys go quiet. Hotels are thin on the ground; more of the beds are rental homes, small fishing lodges and campgrounds. Bahia Honda State Park, MM 37, is a travel idea on this site rather than a match, and its six cabins and campsites are the cheapest good beds down here. They open for booking 11 months ahead for Florida residents and 10 for everyone else, and winter dates go almost at once.
Key West is 45 minutes or less from most of it, Miami about three hours. Stay here for Key West’s evenings without its room rates, if you do not mind a slow drive back in the dark.
Key West: Old Town or New Town
Mile zero, 159 miles from Miami, three and a half to four hours. Rockstar has not shown a Key West, so the end of the road is a travel idea here, but nearly every Keys trip ends at it, and the choice is which half of the island.
Old Town is the historic west end, roughly everything west of White Street: Duval, Mallory Square, wooden houses with porches, and guesthouses in many of them. You can walk everywhere, and you pay for it with the highest rates in the Keys and, often, a parking charge; one resort by Mallory Square publishes a $60 daily resort fee and $40 a night to park. Book it for two nights or fewer and leave the car.
New Town is the east end, from White Street along North and South Roosevelt Boulevard to the airport: chain hotels and shopping plazas a few miles from Duval, with lower rates and shorter minimum stays on busy weekends. You will bike, take a rideshare or drive in. The Duval Loop bus that older guides call free was suspended at the start of 2026, so check the city’s transit page for what runs now.
Florida City and Homestead: the mainland base
Florida’s Turnpike ends at Florida City, the mile markers start just south of it, and Key Largo is about 22 miles on. Rooms cost a fraction of Keys prices. The main entrance of Everglades National Park is about 10 miles southwest of Homestead, so this is a two-region base: a day in the Everglades, which Grassrivers is based on, and a day in the Upper Keys.
It works for a late arrival at Miami International or a first night before an early start. It does not work for Key West: that is six hours or more of driving for one afternoon.
What it costs, by season
The county’s own figures put the average Keys hotel room at about $348 a night across its 2025 fiscal year, and about $290 even in June 2026, a quieter month. A rough guide to a standard double, per night, before tax and fees:
| Base | Late summer and fall | Winter and spring |
|---|---|---|
| Florida City and Homestead | $80-150 | $150-250 |
| Key Largo | $180-320 | $300-550 |
| Islamorada | $250-400 | $400-800 |
| Marathon | $150-250 | $300-450 |
| Big Pine and the Lower Keys | $150-300 | $300-600 |
| Key West, New Town | $180-300 | $350-600 |
| Key West, Old Town | $250-400 | $450-800 |
September is usually cheapest. The most expensive nights are Christmas to New Year, February to April, and Key West’s Fantasy Fest week in late October. Rates move fast, so check before you go; what a Leonida trip costs turns them into budgets.
Fees, taxes and minimum stays
Tax. Keys rooms carry 12.5 percent: 7.5 percent sales tax plus a 5 percent county tourist tax, charged on resort fees too.
Resort fees. Common across the Keys, often $40-60 a night plus tax in Key West. Since May 2025 a federal rule has required hotels and rental sites to show the total price, mandatory fees included, up front. Compare totals, not headline rates.
Minimum stays. Expect two or three night minimums on winter weekends and holidays, and longer ones with bigger deposits at Christmas, New Year and Fantasy Fest. Vacation rentals have a legal twist: in unincorporated Monroe County a home rented for less than 28 days needs a special permit and is banned in some residential zones, and Key West requires a transient license for rentals of 28 days or less. If a house is offered for three nights, ask for its license number.
Booking in hurricane season
Hurricane season runs June 1 to November 30 and peaks from August to October, when rooms are cheapest. Visitors are asked to leave the Keys for any category of hurricane, ahead of residents. The Keys lodging association urges members to refund unused nights once a visitor evacuation order is issued, but each property sets its own policy, so book refundable rates in those months and insure when you book. When to visit has the rest.
Splitting your nights
The pattern that works is one night at each end. Drive down in the afternoon, sleep in Islamorada or Key Largo, and catch the Upper Keys at their best hours: the tiki bars at sunset, the mangroves at dawn. The next day takes the bridges down to Key West for a night or two. That is how the Leonida Keys road trip is built, and the Overseas Highway guide covers the drive.
- Three nights or more: add a night in Marathon or a second in Key West, not a third move.
- A late flight into Miami: first night in Florida City, so you drive the 18-Mile Stretch in daylight.
- A week: two bases, Marathon and Key West, put every place on the Leonida Keys pages within a day’s reach.
The common mistake is moving every night: each move costs a morning of packing and an afternoon waiting for a room.
Updated October 5, 2026. All guides