A week in Key West for eight people works out around $13,500 before flights — $475 a night for a place sleeping four, scaled for the group, plus $81 per adult per day for food. From Atlanta and New York it is cheaper for a family of four to drive than to fly.
The southernmost city in the contiguous United States, at the end of the Overseas Highway. It is known for Duval Street, the sunset gathering at Mallory Square, and Ernest Hemingway's former home.
Lodging and food only. Seven nights, whole-property rental, all fees in.
| Group | Lodging | Food | Total | Per person |
|---|---|---|---|---|
| 4 people | $3,320 | $2,270 | $5,590 | $1,400 |
| 8 people | $8,950 | $4,540 | $13,500 | $1,690 |
| 12 people | $12,200 | $6,800 | $19,000 | $1,590 |
Note the per-person column does not simply fall. A place sleeping four is the efficient unit; going to eight means changing property class, which costs more than double. Past eight it improves again — each additional person adds roughly half what they did over the first jump. The expensive step is condo to house, not the people you put in it.
Averaged across the year, Key West runs $593 a night for a property that sleeps four. That is 101% above the median for all 40 destinations in the library ($295), making it the 5th most expensive of 40 destinations.
Key West is at its most expensive in February and cheapest in May — a 69% swing on the same property.
| Month | Per night, sleeps 4 | |
|---|---|---|
| January | $674 | |
| February | $803 | |
| March | $803 | |
| April | $803 | |
| May | $475 | |
| June | $475 | |
| July | $475 | |
| August | $475 | |
| September | $475 | |
| October | $495 | |
| November | $495 | |
| December | $674 |
The two halves are not priced the same way, which is the whole point: a seat costs per person, a car costs the same whatever the headcount.
| Flying | Driving | ||||
|---|---|---|---|---|---|
| From | Round tripper person | Each wayhours | Round tripper car | Each wayhours | Cheaperfor four |
| Atlanta | $399 | 4.2h | $1,122 | 12.2h2 days | driving |
| Chicago | $453 | 5.5h | $2,113 | 22.5h3 days | flying |
| Dallas | $439 | 5.1h | $1,842 | 19.6h2 days | flying |
| Denver | $494 | 8.2h | $2,845 | 30.2h4 days | flying |
| Los Angeles | $547 | 9.4h | $3,829 | 40.6h5 days | flying |
| New York | $618* | 5.4h | $2,029 | 21.6h3 days | driving |
| Seattle | $586 | 10.3h | $4,544 | 48.2h5 days | flying |
| Phoenix | $514 | 8.6h | $3,215 | 34.1h4 days | flying |
Drives over ten hours are shown in days as well: nobody drives that in one go. The nights on the road are not counted here, so a long drive is cheaper on this page than it would be in life. * published DOT average for that airport pair. Others are modeled from distance. Driving uses the IRS standard mileage rate, which includes running costs, not just fuel.
Compare Key West against other destinations →Lodging is indexed from the US federal per-diem schedule (GSA) for this county, calibrated against real rental listings. Food uses this location's own federal meal tier. Fares come from the DOT Consumer Airfare Report where that airport pair is published, and from a model fitted to 2,089 real DOT fares otherwise. Everything here is an estimate for planning, not a quote — check real prices before booking.