Key West vacation rentals
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Top-rated vacation rentals in Key West
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Key West vacation rentals
Key West house rentals
Serene Lily~ Luxurious 2 bed, 2.5 bath home
Fins to the Left 2 bed 2 bath Duplex w/ Cabana Clu
Waterfront Home 37.5-ft dock, Cabana Club Included
Cozi home with dock
Dream Vacation KCB Marathon with private pool !
The Snapper House 3/2.5 45' dock sleeps 8+ pets OK
P67 - New Construction 3 bedroom 4 bath with priva
Boaters delight! 1 min to open water, Dock & Beach
Key West apartment rentals
Kawama Lagoon, 3D corner chickee 2bdr , 2 baths
Duval Balcony Spanky's Retreat
Studio Near Downtown - The Bartlum
Key's Cottage Escape
#204 Key West Suites
Boho FL Keys Condo
Beachfront Condo w/ Ocean Views in Marathon
3. Oceanside Retreat with Canal Access, Key Largo!
Key West houseboat rentals
A slice of paradise in the Florida Keys
Key Largo's Best Kept Secret!
Aqua Lodge Houseboat "Sea Horse"
Houseboat Getaway In Marathon
Full houseboat with large observation deck
Great Ocean Views! No regrets
Avoid the traffic, Luxury Houseboat on the water
Stella on Stock Island
Quick stats about vacation rentals in Key West
Total rentals
2.2K properties
Nightly prices starting at
ﺩ.ﺇ37 before taxes and fees
Total number of reviews
65K reviews
Family-friendly rentals
1.4K properties are a good fit for families
Pet-friendly rentals
680 properties allow pets
Rentals with a pool
1.7K properties have a pool
Your guide to Key West
All About Key West
Key West is a town that overflows with zest: turquoise waters and sandy beaches, dive bars that never seem to close, stunning sunsets, pastel-hued homes, great American literary legacies, and a sordid haunted past. Chow down on key lime pie and conch fritters, snap a pic at the southernmost point of the continental United States, and take in as much sea and sun as your eyes can handle.
Key West sits right across the Florida Strait from Cuba, and the influence can be felt in many of the island’s favorite haunts, where you can learn to dance the salsa, sample locally distilled rum, and pile your breakfast plate high with sweet fried plantains and savory beans. However you spend your days, make sure that you’re back in Mallory Square before sunset, when live music from restaurant patios and vendors’ stalls fills the pedestrian-only square and people celebrate the show-stopping sunset with all the fanfare it deserves.
The best time to stay in a vacation rental in Key West
Winter is the most popular season in Key West, as the hot weather draws sun-seekers to the beaches, especially around the December holidays. You can also come in spring for sun and fewer crowds — despite Key West’s bustling nightlife scene, it isn’t typically hit by Spring Break crowds like other places in Florida. It’ll be warm enough to get in the water and enjoy beach time, with fewer people than in winter. Despite a September to November hurricane season, autumn is also a good time to check out Key West’s museums or to revel in the hedonistic Fantasy Fest while enjoying cooler air.
Top things to do in Key West
Snorkeling
Home to the only living Barrier Reef in the continental United States, Key West has some of the most incredible snorkeling in the world. Head out to the cluster of tiny islands known as the Dry Tortugas National Park for the best of the best: this area is home to unspoilt coral reefs, hundreds of species of tropical fish, starfish, and conch.
Ghost tours
Key West is rumored to be one of the most haunted cities in America, in juxtaposition with its sunny, good-time appearance. For fans of classic horror, be sure to ask about a famous local doll and the film franchise he inspired. Listen to ghost stories on board a spooky train tour, go on a guided walk around town, or check out the quirky inscriptions on the local graves at the cemetery.
Key lime pie
Key lime pie can be found on just about any menu here, from dive bars to high-end bistros, and with good reason — the island’s eponymous pie is zesty, creamy, and delicious. Traditionally made from tangy key lime juice and a rich, sweet custard of egg yolk and condensed milk atop a crust, everybody from home cooks to renowned chefs has their own take on how it should be made. Try as many versions as you can while you’re here, and join in on the debate of cooked versus uncooked filling, graham cracker versus pie crust, and whipped cream versus meringue topping.
Frequently Asked Questions
How is the weather in Key West?
Key West has a tropical climate with warm temperatures year-round. Summers, from June to August, can be hot and humid, often reaching 90°F (32°C). Winters, from December to February, are milder, with temperatures typically around 70°F (21°C), and less rainfall.
What are some of the best things to do in Key West?
Popular activities in Key West include exploring the vibrant coral reefs on a snorkeling trip, discovering local marine life at the Key West Aquarium, or visiting the historic Fort Zachary Taylor State Park. A stroll along Duval Street for shopping and local cuisine is also recommended.
What is the best time of year to visit Key West?
Key West is particularly lively between March and May, with milder temperatures and fewer crowds. During these months, you can enjoy events like the Conch Republic Independence Festival and the Key West Songwriters Festival.
What are the best places to stay in Key West?
Some highly-rated areas to stay in Key West include Old Town, a historic district with classic architecture, Truman Annex for its peaceful atmosphere, and New Town for its modern conveniences. Duval Street is also favored for its proximity to dining and shopping options.
What are the best places to visit in Key West?
Key West is known for diverse attractions such as the Ernest Hemingway Home and Museum, where the renowned author once lived, and the Key West Butterfly and Nature Conservatory. Don't miss the stunning sunsets at Mallory Square, and the view from the historic Key West Lighthouse. The Southernmost Point Buoy is also frequently visited.
What are some hiking trails in Key West?
While Key West is not known for its hiking, you can enjoy a leisurely walk at the Key West Tropical Forest and Botanical Garden. The Island City National Historic District also has interesting paths through the town's picturesque streets.
What are some family activities to do in Key West?
Families can enjoy a visit to the Key West Shipwreck Museum, engage with interactive exhibits at the Florida Keys Eco-Discovery Center, or have fun exploring the Key West Aquarium. A ride on the charming Conch Tour Train is also a delightful way to see the city.
What are some of the best day trip ideas in Key West?
For a memorable day trip, explore the natural beauty of Dry Tortugas National Park, which is accessible by ferry or seaplane. Also, consider a wildlife expedition at the Key West Wildlife Center, or learn more about the region's history with a visit to Fort East Martello Museum.
What types of vacation rentals are available in Key West?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Key West. From over 430 condo rentals, over 40 cottage rentals, over 20 houseboat rentals, over 330 apartment rentals to over 640 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
Are there vacation rentals with a dedicated workspace in Key West?
Yes! Work meets play with ease at over 1,140 vacation rentals in Key West featuring dedicated workspaces. Stay connected and productive in your home away from home.
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