About a 3.5-hour drive from Miami, Key West is known for its warm, sun-drenched beaches, inclusive resorts, oceanfront vacation homes, key lime pie, and a vivacious “anything goes” ethos. Do like the locals do on your Key West vacation and see where their live-in-the-moment attitude takes you. Perhaps you’ll end up dancing to live music on Duval Street or deep-sea fishing out in the Gulf Stream. Playing on tropical championship golf courses or riding scooters at sunset.
This seven-square-mile island is a quintessential tropical oasis by day, and a lively party paradise by night. Most of the buzz happens around Mallory Square and Duval Streets, both packed with bars, restaurants serving Caribbean and Cuban food, and cruise ship passengers in search of lively fun. It’s little wonder that Key West vacation rentals and hotels are quick to book up — especially those with coveted amenities like private balconies with Atlantic views, free parking, pet-friendly guest rooms, watersports rentals, and on-site restaurants. There are rentals in Key West for every kind of vacationer.
Vacation rentals in Key West have a price range between $67-$5,080. The average price for rentals in Key West is $349 per night.
There are 1,993 vacation rentals available in Key West across several booking partners.
Head to the marina area of Key West at Stock Island for fresh seafood and choice fishing spots. Charter a fishing excursion or rent a sailboat to experience Key West from the water.
Mallory Square is a busy waterfront plaza with bars, restaurants, and shops. Walk along the boardwalk where boats dock in the harbor or catch an amazing sunset sipping cocktails at a local eatery.
Duval Street is a mile-long strip stretching north to south in the downtown area where locals and visitors are drawn to the action. Stroll along the street lined with historical museums, pubs, and cozy cafes.
Yes! Key West is very LGBTQ-friendly and is a longtime favorite travel destination for LGBTQ+ travelers, with many gay- and lesbian-owned hotels and vacation homes, plus bars and restaurants catering to LGBTQ+ visitors. The town even has a motto to show its inclusiveness: “One Human Family.”
The best time to visit Key West is between March and May when the winter crowds thin out and prices tend to drop. You’ll find the best hotel rates during hurricane season, which typically runs from November to June.
Houses are the top rental type in Key West, with 1,993 rentals currently available.