Key West vacation rentals

There are loads of different property types that you can make your vacation home in Key West. You’ll find apartments, boats, cabins, campgrounds, caravans, condos, cottages, houses, homestays, hotels, houseboats, lodges and villas.

There are a number of dog and pet-friendly Key West vacation rentals, with around 12% allowing you to bring your pet along with you.

In the last 72 hours, users have found Key West vacation rentals for tonight for as low as ₪645. Search here for similar prices

Vacation rentals in Old Town South of Truman, Truman Annex and Old Town North of Truman have the most searches on KAYAK. For more information about Key West's different neighborhoods, check out our Key West's City Guide.

Take a look at our vacation rentals map to find the best vacation rental homes near you.

New Town is a great place to stay for those with families. It’s quieter and calmer, with plenty of shops to easily stock up on groceries. Bonus points for being close to Key West International Airport. Sunrise Suites - Great Exuma Suite #406 will comfortably accommodate a family of six.

Duval Street is the most active area of the night in Key West, with bars, late-night restaurants and nightclubs and live music every night in many establishments. Charming, a dog-friendly home in a residential neighbourhood in Casa Marina, is steps away from Duval Street.

A holiday rental in Truman Annex like Hyatt Residence Club Key West is as safe as it gets, as the neighbourhood is a private gated community. It is a longer walk to Duval Street and other attractions than other neighbourhoods, but it also boasts a museum that was a former residence of President Harry Truman.

New Town has contemporary shopping areas, but for an authentic Key West experience, you might like to stay in Newly Remodelled First Floor, to visit the popular flea market of Bahama Village.

Bahama Village is lucky enough to also be one of the best areas for food, with Spanish tapas from Santiago's Bodega or brunch from the famous Blue Heaven. Decent food can also be had near the seaport of Old Town, with authentic Cuban food from Meson de Pepe’s, or seaside views at the Half Shell Raw Bar. Traveler's Palm is another accommodation in Bahama Village.