Vacation rentals in Key West
Key West is the final island on the Overseas Highway, 90 miles from Cuba: a tiny walkable world of conch cottages, Hemingway lore, nightly sunset celebrations, and water so clear it looks filtered.
Best time to book
December through May for dry, breezy perfection; September–November brings the lowest rates and warmest water.
Common rental types
Conch cottages · Old Town guesthouses · Historic homes with pools · Marina-view condos
Getting there
Fly into Key West International (EYW) or drive the 113-mile Overseas Highway from Miami (about 3.5–4 hours, spectacular). Once there, you won't need a car.
Looking for bookable deals?
Our partner A1 Vacation Homes adds new special offers every week — see what's live across all destinations right now.
Vacation rentals in Key West
Listings for Key West are coming soon
We're adding real rentals for this destination right now. In the meantime, browse the bookable deals above or check another destination.
Where to stay in Key West
Old Town
The heart of it all — Duval Street, Hemingway Home, Mallory Square, and most classic cottages.
Casa Marina & South
Leafy residential lanes near the island's best beaches, Higgs and Smathers.
Truman Annex
Gated, manicured enclave between Mallory Square and Fort Zachary Taylor State Park.
New Town
The island's east side — marinas, shopping, and better-value stays.
Learn Key West before you book
Neighborhoods, seasons, and booking tips — the full destination guide.
Read the Key West guide