Key West vacation rentals

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Top-rated houses for rent in Key West

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite
Home in Key West
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.
Dec 28 – Jan 4
$528 per night
4.94 out of 5 average rating, 265 reviews
Guest favorite
Home in Cudjoe Key
Cudjoe Key Home with a View
We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.
Aug 15 – 22
$278 per night
4.96 out of 5 average rating, 113 reviews
Guest favorite
Home in Marathon
Sea Ray Cove , 75’ boat dock, 1 block from beach!
2024 - New Weber grill This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.
Aug 23 – 30
$399 per night
4.99 out of 5 average rating, 103 reviews

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 houses

Superhost
Home in Cudjoe Key
OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
Aug 23 – 30
$349 per night
4.81 out of 5 average rating, 218 reviews
Superhost
Home in Upper Sugarloaf Key
Bungalows at Sugarloaf Beach - The Lighthouse
Jul 3 – 10
$717 per night
4.84 out of 5 average rating, 38 reviews
Guest favorite
Home in Key West
Butterfly Cottage ~ Enjoy hot tub, gourmet kitchen
Jul 9 – 16
$609 per night
5.0 out of 5 average rating, 19 reviews
Guest favorite
Home in Key West
Gorgeous Romantic Private Villa, Steps from Duval!
Feb 7 – 14
$664 per night
5.0 out of 5 average rating, 30 reviews
Guest favorite
Home in Key West
Paradise found
Feb 14 – 21
$449 per night
4.96 out of 5 average rating, 49 reviews
Guest favorite
Home in Key West
Hot tub Conch House just steps to Duval/Sleeps 6
May 13 – 20
$908 per night
4.89 out of 5 average rating, 54 reviews
Guest favorite
Home in Key West
Clean and Relaxing! 3 King Suites! With everything
Sep 27 – Oct 4
$684 per night
5.0 out of 5 average rating, 62 reviews
Superhost
Home in Cudjoe Key
*Emerald Seas*-Florida Keys Ocean Front Paradise!
May 29 – Jun 5
$650 per night
4.83 out of 5 average rating, 35 reviews
Superhost
Home in Cudjoe Key
Spanish Queen @Venture Out
Jun 12 – 19
$332 per night
4.86 out of 5 average rating, 42 reviews
Superhost
Home in Key West
Your clean and cosy family home in Key West
Aug 1 – 8
$615 per night
4.84 out of 5 average rating, 43 reviews
Guest favorite
Home in Marathon
Beautiful Beachfront Home w/ Pool/Tiki/Dock
Nov 27 – Dec 4
$870 per night
4.9 out of 5 average rating, 52 reviews
Superhost
Home in Marathon
Marathon Beach Home
Sep 1 – 8
$366 per night
4.86 out of 5 average rating, 7 reviews

Key West condos

Superhost
Condo in Key West
Beach Club Ocean Front 2BR Condo
Jul 23 – 30
$613 per night
4.93 out of 5 average rating, 132 reviews
Guest favorite
Condo in Key West
A Perfect Getaway
Sep 5 – 12
$437 per night
4.85 out of 5 average rating, 120 reviews
Guest favorite
Condo in Key West
Spacious Updated Waterfront Condo, 2/2 Pool, Dock
Aug 29 – Sep 5
$497 per night
4.86 out of 5 average rating, 118 reviews
Guest favorite
Condo in Key Colony Beach
Oceanfront Breeze, Stunning Views, Beach/Pool
Oct 30 – Nov 6
$298 per night
4.92 out of 5 average rating, 189 reviews
Guest favorite
Condo in Key West
La Dolce Vita, Old Town Steps to Duval! 3 blks bch
Sep 3 – 10
$266 per night
4.83 out of 5 average rating, 235 reviews
Superhost
Condo in Key Colony Beach
Beachside Unit 28 - Private Beach, Pool & Paradise
Nov 10 – 17
$203 per night
4.79 out of 5 average rating, 102 reviews
Guest favorite
Condo in Key West
Moonlight Paradise Upgraded Family oasis Tropical
Jul 1 – 8
$507 per night
4.85 out of 5 average rating, 106 reviews
Guest favorite
Condo in Marathon
Sombrero Beach Tropical Getaway
Aug 14 – 21
$200 per night
4.88 out of 5 average rating, 179 reviews
Guest favorite
Condo in Key West
Hidden Beach Duplex, Best Place in Key West
Nov 27 – Dec 4
$608 per night
4.99 out of 5 average rating, 83 reviews
Superhost
Condo in Key West
Ocean Front Studio private Sandy Beach in Key West
Dec 7 – 14
$336 per night
4.89 out of 5 average rating, 72 reviews
Guest favorite
Condo in Key West
*Come to my Deck for a time you won't Forget!
Sep 17 – 24
$270 per night
4.99 out of 5 average rating, 76 reviews
Guest favorite
Condo in Key West
The Island Suite @ KW vacation
Aug 24 – 31
$408 per night
4.88 out of 5 average rating, 59 reviews

Key West cottages

Guest favorite
Cottage in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
Sep 13 – 20
$416 per night
4.91 out of 5 average rating, 142 reviews
Superhost
Cottage in Cudjoe Key
ATLANTIS...Ocean Front Cottage Retreat!
Jul 26 – Aug 2
$725 per night
4.91 out of 5 average rating, 128 reviews
Superhost
Cottage in Key West
Namaste: A blissful one bedroom cottage
Nov 25 – Dec 2
$563 per night
4.86 out of 5 average rating, 28 reviews
Guest favorite
Cottage in Key West
Casa Serendipity @ Old Town - Private Home & Pool
Sep 8 – 15
$614 per night
5.0 out of 5 average rating, 26 reviews
Guest favorite
Cottage in Cudjoe Key
King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks
Oct 19 – 26
$442 per night
4.9 out of 5 average rating, 71 reviews
Guest favorite
Cottage in Key West
The Dancing Rooster
Oct 9 – 16
$568 per night
4.9 out of 5 average rating, 86 reviews
Guest favorite
Cottage in Marathon
Catch n' Relax Canalfront Cottage in Marathon
Dec 4 – 11
$251 per night
4.95 out of 5 average rating, 20 reviews
Cottage in Key West
1 bedroom Cottage
Mar 28 – Apr 4
$680 per night
4.74 out of 5 average rating, 336 reviews
Cottage in Key West
1BR | Dog Friendly | Deck | Grill | AC
Sep 4 – 11
$233 per night
4.72 out of 5 average rating, 123 reviews
Cottage in Cudjoe Key
VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck
Oct 9 – 16
$159 per night
4.61 out of 5 average rating, 89 reviews
Cottage in Cudjoe Key
Calypso Cottage
May 6 – 13
$269 per night
4.67 out of 5 average rating, 110 reviews
Guest favorite
Cottage in Key West
A Touch of Bermuda in Key West
Sep 12 – 19
$420 per night
5.0 out of 5 average rating, 7 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 30 cottage rentals, over 410 condo rentals to over 520 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 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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  4. Monroe County
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