Island City House Hotel A Condominium
State licensed
The Florida Keys · 829 licensed rentals
Key West vacation rentals
Key West is the end of the road: mile marker 0 on US-1 and the southernmost city in the continental US. Old Town is the part most people picture, a grid of wooden conch houses with tin roofs and deep porches, Duval Street running down the middle, and Mallory Square on the harbor, where a crowd gathers every evening to watch the sun go down.
Old Town is flat and small enough that many guests park the car for the week and get around on foot or by bike. Stock Island, across the bridge to the east, is the working waterfront, with commercial fishing boats, marinas and a slower feel. Key West has some of the strictest short-term rental rules in the Keys, so confirm the minimum stay with the owner before you book.
Things to do near your rental
- Sunset at Mallory Square on the harbor
- Duval Street and the Old Town historic district
- Fort Zachary Taylor Historic State Park beach
- Ferry or seaplane to Dry Tortugas National Park
Licensed by the state of Florida
829 Key West vacation rentals
Every listing starts from an active state license. Owners who claim their listing add photos, rates and a direct booking link, and appear first.
Bayview House
State licensed
Mango Cottage
State licensed
Casa Buena
State licensed
Casa Key Largo
State licensed
Hollinsed House
State licensed
Elsewhere in the Keys
Compare other parts of The Florida Keys
- Vacation rentals in the Lower Keys 216 licensed · Boating, snorkeling, fishing, quiet canal-front stays
- Vacation rentals in Marathon 1,771 licensed · Families, boaters, longer stays, a central base for day trips
- Vacation rentals in Islamorada 206 licensed · Fishing charters, boating, sandbar days, bayside sunsets
- Vacation rentals in Key Largo 430 licensed · Diving and snorkeling, short trips from Miami, kayaking
Key West rental questions
How do I get to the Dry Tortugas from Key West?
Dry Tortugas National Park is about 70 miles west of Key West and reachable only by boat or seaplane. Most visitors take the ferry or a seaplane from Key West for a day at Fort Jefferson. Trips fill up in season, so reserve them before you lock in your rental dates.