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Key West vacation rentals

Book unique houseboats, vacation rentals, and more on Airbnb

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Stay near Key West's top sights

Duval Street62 locals recommend
Mallory Square100 locals recommend
Key West Butterfly and Nature Conservatory56 locals recommend
Fort Zachary Taylor Historic State Park47 locals recommend
Higgs Beach21 locals recommend
Sebago Watersports6 locals recommend

Key West houseboats

Guest favorite
Houseboat in Tavernier
Aqua Lodge Houseboat "Sea Horse"
Oct 4 – 11
$398 per night
4.88 out of 5 average rating, 67 reviews
Houseboat in Marathon
Houseboat Heaven -Private Island
Feb 12 – 19
$446 per night
New place to stay
Houseboat in Stock Island
Stella on Stock Island
May 11 – 18
$300 per night
New place to stay
Houseboat in Marathon
Farándula at Sea House
Nov 23 – 30
$193 per night
4.1 out of 5 average rating, 10 reviews
Superhost
Houseboat in Key West
Key West Houseboat Paradise
Jan 18 – 25
$349 per night
4.8 out of 5 average rating, 247 reviews
Guest favorite
Houseboat in Islamorada
Getaway to Blackbeard's Hideout
Nov 1 – 8
$269 per night
4.9 out of 5 average rating, 10 reviews
Guest favorite
Houseboat in Islamorada
Aqua Lodge in the Florida Keys!
May 9 – 16
$269 per night
4.83 out of 5 average rating, 6 reviews
Guest favorite
Houseboat in Stock Island
Great View in a private marina!
Jun 28 – Jul 5
$650 per night
4.86 out of 5 average rating, 21 reviews

Key West houses

Guest favorite
Home in Key West
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
Jul 9 – 16
$451 per night
4.94 out of 5 average rating, 267 reviews
Superhost
Home in Key West
Rooftop Penthouse - Luxury Penthouse in prime Down
Jan 22 – 29
$711 per night
4.85 out of 5 average rating, 108 reviews
Guest favorite
Home in Marathon
Oceanfront Tiny Villa in the Heart of the FL Keys
Aug 10 – 17
$391 per night
4.96 out of 5 average rating, 118 reviews
Guest favorite
Home in Marathon
Beachfront Villa - Florida Keys
Oct 14 – 21
$350 per night
4.9 out of 5 average rating, 154 reviews
Guest favorite
Home in Marathon
Marathon one-level home on the Marina - with slip!
Jun 23 – 30
$523 per night
4.97 out of 5 average rating, 116 reviews
Guest favorite
Home in Cudjoe Key
Paradise and Cudjoe Bay
May 30 – Jun 6
$335 per night
4.92 out of 5 average rating, 133 reviews
Guest favorite
Home in Cudjoe Key
Cudjoe Key Home with a View
Aug 28 – Sep 4
$323 per night
4.96 out of 5 average rating, 114 reviews
Guest favorite
Home in Key Largo
Your Keys Getaway!
Jan 25 – Feb 1
$152 per night
4.9 out of 5 average rating, 344 reviews

Key West condos

Superhost
Condo in Key West
Beach Club Ocean Front 2BR Condo
Jul 7 – 14
$728 per night
4.93 out of 5 average rating, 132 reviews
Guest favorite
Condo in Key Colony Beach
Oceanfront Breeze, Stunning Views, Beach/Pool
Nov 4 – 11
$298 per night
4.92 out of 5 average rating, 190 reviews
Guest favorite
Condo in Key West
Large 2/2 Waterfront Condo Great View Pool & Dock
Oct 9 – 16
$497 per night
4.79 out of 5 average rating, 153 reviews
Guest favorite
Condo in Key West
A Perfect Getaway
Sep 19 – 26
$426 per night
4.85 out of 5 average rating, 122 reviews
Guest favorite
Condo in Key West
Moonlight Paradise Upgraded Family oasis Tropical
Aug 17 – 24
$344 per night
4.85 out of 5 average rating, 106 reviews
Guest favorite
Condo in Key Colony Beach
Beachside Unit 39 Tiki Huts, Private Beach & Pool
Aug 14 – 21
$203 per night
4.92 out of 5 average rating, 110 reviews
Guest favorite
Condo in Key West
La Dolce Vita, Old Town Steps to Duval! 3 blks bch
Feb 22 – Mar 1
$439 per night
4.83 out of 5 average rating, 235 reviews
Guest favorite
Condo in Marathon
Sombrero Beach Tropical Getaway
Dec 3 – 10
$204 per night
4.87 out of 5 average rating, 185 reviews

Quick stats about vacation rentals in Key West

Total rentals

1.8K properties

Rentals with a pool

1.2K properties have a pool

Pet-friendly rentals

490 properties allow pets

Family-friendly rentals

1.1K properties are a good fit for families

Total number of reviews

52K reviews

Nightly prices starting at

$10 before taxes and fees

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 520 house rentals, over 10 houseboat rentals to over 410 condo 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 910 vacation rentals in Key West featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

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