Where to Stay
Where to Stay in Key West for the First Time
Choose a first-trip base by walking needs, room style and daily plans—not just a hotel’s use of the words Old Town.
Read Guide →Choose your base
Staying in Old Town
Historic character beyond the Downtown core.
A feel for the area
Guesthouses and historic character. Walking distances and the feel of each street vary.
- Best for
- Guesthouse atmosphere, historic streets and a calmer-feeling base.
- Getting around
- Walking and cycling can work well; check the exact address and your intended stops.
- Why stay here
- Stay among older streets while choosing how close you want to be to the busiest blocks.
- Think twice if
- You need every central stop on your doorstep. Distances and noise vary by location.
- Orientation
- Old Town occupies the historic western side of Key West and includes Downtown. For stays, this option emphasizes streets outside that central core.
Real island outlines; editorial planning zones, not official neighborhood boundaries. Downtown is within Old Town.
Staying in Old Town
How do you like to stay?
Choose a stay type to see our curated recommendations.
Choose the stay that fits your trip.
Where to Stay
Is Stock Island a Good Place to Stay?
Stock Island suits a marina- or resort-oriented trip, but central Key West becomes an outing rather than the setting outside your room.
Read Guide →Where to Stay
Hotels, Guesthouses or Vacation Rentals in Key West?
Compare service, room layout, guest policies and rental periods before choosing the accommodation type for your trip.
Read Guide →These are editorial planning areas, not official neighborhood boundaries. Compare the setting first, then the exact property, room and daily journeys.