Key West Vacation Rentals

Unlock your dream Key West Vacation Rental

Live like a Conch (local) with a Key West vacation rental getaway

Head to a place of pastel houses and thick palm trees swaying in the salty air and put your bags down in your very own Key West vacation rental. Stroll down Duvall Street after a slice of Key Lime pie, find your new favorite rum bar, then join the flocks lining up to watch the sunset in Mallory Square. You can get busy doing nothing or take it easy doing plenty, before unwinding at your own slice of paradise—whether it’s a modern motel with ocean views, a cute townhouse in historic Old Town Key West, or a private vacation home hideaway on the waterfront.

Prices start at just $99 and go up to $329 a night for deluxe Key West vacation rentals—so there’s a property for every budget. Remember prices and availability are subject to change, and additional terms may apply.

Uncover your perfect vacation rental in Key West Florida

Our filters and map make it easy to narrow your Key West vacation rental search by price, location, and amenities. If you’re bringing along your four-legged pal, use the pet-friendly filter to find a getaway that welcomes your furry buddy. Check out this dog-friendly 2-bedroom condo with a west-facing private deck for snuggles at sunset. If you crave a cool dip after a day exploring, the pool filter shows you all the vacation rentals with pools. This studio apartment in Old Town Key West has a heated pool and includes bikes for getting around like a Conch. If the idea of waking up to the sound of lapping waves is pure heaven, use our map to find places to stay on the waterfront. This 3 bedroom, 4 bathroom waterfront vacation home comes with its own private dock so you can rent a boat and explore the local islands, too.

How to find Key West vacation rental deals

For some terrific vacation rental deals in Key West, enter your travel dates and hit search to discover some of the best vacation rentals in Key West, FL. You can then filter by price, rating, or location to find your ideal vacation spot. If you have flexible travel dates, try adjusting those to see different prices, or book your stay during , when it’s usually easier to find great cheap Key West vacation rentals compared to when bookings are popular, and prices can be higher.

Why choose a vacation rental in Key West FL with Expedia?

At Expedia, you can easily compare top vacation rentals in Key West all in one place, then simply click to book the best one for you. We’ve locked in low prices on a vast number of properties, many with buy now, pay later options. You also save money when you bundle your flight and rental car bookings. If you book a vacation rental in Key West with free cancellation, you can rest easy knowing if your plans change you won’t be out of pocket. So, let Expedia help you get away to your dream vacation rental in the USA’s southernmost city and feel a world away.