Key West Travel Guide

Key West is the most expensive place to sleep in Florida and one of the cheapest to enjoy once you're there. Duval Street, the Southernmost Point, Mallory Square sunset, and Higgs and Smathers beaches are all free, and the island is small enough that a bike replaces a rental car entirely. The cost curve is seasonal and steep: winter into spring is high season with the year's top rates, while late summer and early fall — hurricane season — see the deepest discounts. Driving the Overseas Highway from Miami is a four-hour trip that's part of the experience. This guide covers timing, getting around, and where the value lodging actually is.

Quick tips

• Rent a bike, not a car — the island is small and parking is a constant expense.
• Mallory Square sunset, the Southernmost Point, and the beaches are free.
• Late August through October is hurricane season and by far the cheapest window.
• Staying in Marathon or Key Largo costs far less if you're willing to drive in.
• Happy hour is a real strategy here; Duval prices drop sharply before evening.

Frequently asked

When is Key West cheapest?

Late August through October, during hurricane season. December through April is high season with the year's highest rates.

Do you need a car in Key West?

No. Once you're on the island, biking or walking covers everything, and skipping parking fees saves real money.

How long is the drive from Miami to Key West?

About four hours on the Overseas Highway, longer with stops. It's a scenic drive worth budgeting daylight for.