Florida

Key West vacation rentals

The end of the road — sunsets, six-toed cats, and the freest spirit in America.

Best time to visit

December through May for dry, breezy perfection; September–November brings the lowest rates and warmest water.

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.

About Key West

Key West has been a haven for writers, wreckers, shrimpers, and free spirits for two centuries, and it wears its history lightly: gingerbread-trimmed conch houses, roaming roosters, and the densest collection of bars in Florida. Ernest Hemingway wrote here for a decade; his house and its famous six-toed cats remain the island's beloved landmark.

Every evening the island gathers at Mallory Square for the sunset celebration — street performers, conch fritters, and a green-flash hope. The surrounding water is protected as the Florida Keys National Marine Sanctuary, and the third-largest barrier reef in the world lies seven miles offshore. The middle keys (Marathon) and the upper keys (Key Largo) are the stops along the way down.

Vacation rentals in Key West

Key West vacation rentals are as individual as the island: restored conch cottages with private pools hidden behind picket fences, grand Old Town Victorians, and marina-view condos in New Town. Old Town puts you on foot to everything; Casa Marina and the Truman Annex are quieter and closer to the best swimming.

This is a small island with big demand — book winter and festival weeks (Fantasy Fest in October, Songwriters Festival in May) six months out. Many historic cottages are intimate one- and two-bedrooms, so groups should look at multi-unit compounds or New Town homes. Rates drop noticeably from late August through early December.

Things to do in Key West

Celebrate sunset at Mallory Square, then stroll Duval Street
Tour the Hemingway Home and meet the six-toed cats
Snorkel or dive the reef, or ferry 70 miles to Dry Tortugas National Park
Swim at Fort Zachary Taylor State Park, the island's best beach
Visit the Little White House and the Key West Butterfly Conservatory
Eat key lime pie, conch fritters, and fresh catch at a dockside shack

Getting around and who it's for

Key West is two miles by four — ditch the car. Walk, bike, or scooter everywhere; parking in Old Town is scarce and expensive. Couples and friend groups get the most from the nightlife and dining; families do best near the beaches in Casa Marina with day trips to the reef and Dry Tortugas.

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.

Key West FAQs

Is Key West worth the drive?

Yes — the Overseas Highway itself is one of America's great road trips, with 42 bridges over open ocean. Once in Key West, the walkable Old Town, water clarity, and sunset culture are unlike anywhere else in the US.

How many days do you need in Key West?

Three to four days covers Old Town, a reef or Dry Tortugas trip, and beach time without rushing. Add days if you're combining with Marathon or Key Largo on the drive down.

When is hurricane season in Key West?

June through November, with peak risk August–October. Many travelers visit then anyway for the lowest rates — just book refundable stays and watch the forecasts.