Key West Vacation Rentals

Explore our Key West, FL, vacation rentals

With a mix of island charm, thrilling water sports, and unforgettable experiences, Key West vacation rentals offer a getaway you’ll want to return to again and again. The island, the southernmost of the Florida Keys, boasts a rich history, with attractions like the Ernest Hemingway Home and Museum, the Harry S. Truman Little White House, and the Historic Key West District. Tour through the 187 historic buildings or hit the beach for one of the island’s main attractions: water sports.

Key West is a water sports enthusiast's dream, with the perfect backdrop for fishing, snorkeling, diving, paddleboarding, and more. It's also a gateway to the Dry Tortugas National Park, a remote and pristine island group accessible by seaplane and the popular Yankee Freedom ship. Back on land, be sure to explore the town and its must-see spots, like Duval Street’s lively mix of bars, restaurants, shops, and entertainment venues, as well as Smathers Beach and Fort Zachary Taylor State Park.

Where is Key West, FL?

Key West is located in the southernmost part of Florida, USA. It is an island city situated at the southern tip of the Florida Keys archipelago, and it is approximately 90 miles north of Cuba. It is connected to the mainland of Florida by the Overseas Highway, a scenic road that stretches across numerous islands of the Florida Keys.

Things to do in Key West, FL

Kick back on island time with a Key West vacation home and immerse yourself in a world of rich history, delicious cuisine, and beach fun. 

• It’s not a proper visit to the Key West without visiting the Southernmost Point Buoy. The landmark buoy marks the southernmost point in the continental United States, resting just 90 miles from Cuba. Be sure to grab a photo op by the marker buoy. 
• Pristine Gulf Coast beaches are a big draw for many travelers to the Key West, and with one step on these golden sands, you’re sure to see why. Build sand castles, comb for shells, or laze under the sunshine at popular beach and park spots like Fort Zachary Taylor Historic State Park, Smathers Beach, and Higgs Beach.
• Key West offers a plethora of water activities, from snorkeling amidst vibrant coral reefs to sailing into the horizon on a catamaran sunset cruise. Take a seaplane or boat ride over to Dry Tortugas National Park to snorkel and scuba dive or charter a fishing tour for incredible trophy fish catches.
• Indulge your taste buds with the island's culinary delights, including fresh seafood and the world-famous Key lime pie. Enjoy the island's unique dishes, including conch fritters and Key West pink shrimp, at a seafood restaurant by the water. No worries if seafood isn’t your style—Key West also boasts a number of authentic Cuban restaurants, Caribbean-fusion eateries, and cocktail bars.
• Visit the iconic landmarks that define Key West, such as the Key West Lighthouse, the Mel Fisher Maritime Museum, and the Ernest Hemingway Home and Museum, where you can meet the descendants of Hemingway's beloved six-toed cats.
• As the sun sets, join the lively crowd at Mallory Square to witness a spectacular sunset celebration, complete with street performers, music, and a breathtaking view of the sun dipping below the horizon.
• Traveling with little ones? Key West has plenty of fun in store for both the young and the young at heart. Enjoy kid-friendly activities like dolphin cruises, the Key West Butterfly and Nature Conservatory, the Florida Keys Eco-Discovery Center, and the Key West Tropical Forest & Botanical Garden.
• Key West hosts various festivals throughout the year, such as Fantasy Fest and the Key West Songwriters Festival, adding to its vibrant and festive atmosphere,  so be sure to plan your vacation in time to participate in festivals. 

Does Vacasa offer snowbird or long-term rentals in Key West?

Yes, Vacasa has plenty of long-term, monthly, and snowbird rentals in Key West and throughout Florida. Stay close to the beach with an oceanfront beach house rental, resort condo rental, or vacation home with plenty of room for you and your crew. Find amenities like boat docks and slips, direct beach access, tennis courts, and outdoor pools.

Book a Key West house rental, condo, or cottage

Whether you're seeking adventure, relaxation, or a taste of Key West's famous Key lime pie, this island paradise offers a memorable vacation experience for travelers of all kinds. So, pack your flip-flops, grab your sunglasses, and get ready to savor the magic of Key West, where every day feels like a vacation in paradise. Find your perfect Key West vacation rental.

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