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Key West vacation rentals

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Top-rated vacation rentals in Key West

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

Superhost
Apartment in Key West
Bella Vita: 1B/1B Condo for 2 Just Steps off Duval
1B/1B condo located in Old Town less than 1/2 block from Duval St. & a couple blocks from the Southernmost Point, Hemingway House & many other Key West attractions. Bella Vita accommodates 2 adults only and features a large porch with chairs & table, living room with leather sofa, galley kitchen with bar seating, king-size bed with Tempurpedic mattress, desk area, bathroom with large walk-in shower, wi-fi, sound machine, 2 Smart TVs, DVD players & BlueTooth stereo system with CD player & radio.
$275 per night
Superhost
Apartment in Key West
Key West - Sunset ❀ The Green House
Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable price and enjoy! ♡ Best location for exploring Key West, in the epicenter of Old-Town and all attractions. One corner from world-famous Sloppy Joe's (Hemingway's favorite place) and Duval Loop, the free local ride. Check out the map and see all attractions right around The Green House!
$219 per night
Superhost
Apartment in Key West
Honeymoon Hideaway, King bed, Private Deck & Spa!
Pale blue interiors, small efficiency kitchen, platform Pottery Barn King memory foam bed with multiple basket drawers underneath for storage, large shower. Large private deck with 2 person spa, hammock, outdoor sofa and table/chairs. Bose Bluetooth speaker, Alexa. Private gated compound and gated entrance to Honeymoon Hideaway. Renovated August, 2019 with new full bathroom and designer kitchen with dishwasher, 2 burner stove, refrigerator with freezer, microwave!
$417 per night

Stay near Key West's top sights

Mallory Square100 locals recommend
Southernmost Point of the Continental US64 locals recommend
The Ernest Hemingway Home and Museum105 locals recommend
Key West Butterfly and Nature Conservatory56 locals recommend
Fort Zachary Taylor Historic State Park47 locals recommend
Higgs Beach21 locals recommend

Key West house rentals

Superhost
Home in Key West
Casa Cristol - Family Friendly Classic KW Charm
$636 per night
Superhost
Home in Key West
Rooftop Penthouse - Luxury Penthouse in prime Down
$793 per night
Superhost
Home in Key West
Home Away from Home with Free parking
$228 per night
Superhost
Home in Cudjoe Key
OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
$283 per night
Superhost
Home in Key Colony Beach
Private Corner Lot, Wide Water Views, 30' Dock
$251 per night
Superhost
Home in Cudjoe Key
Cudjoe Key Home with a View
$266 per night
Superhost
Home in Marathon
Waterfront Cozy Modern Retreat w/Deep Canal
$166 per night
Superhost
Home in Cudjoe Key
Newly Renovated Oceanside House with Pool
$275 per night
Superhost
Home in Key West
Key West House
$166 per night
Superhost
Home in Key West
John Truman's Hideaway~ Walk to Duval Street
$230 per night
Superhost
Home in Key West
Gorgeous Romantic Private Villa, Steps from Duval!
$550 per night
Superhost
Home in Key West
Private Paradise with Heated Waterfall Pool
$270 per night

Key West apartment rentals

Superhost
Apartment in Key West
Duval St Apartment w/ Balcony w/parking Adult Only
$375 per night
Superhost
Apartment in Key West
Studio Blu - Key West, FL - Hip Studio in Old Town
$180 per night
Superhost
Apartment in Key West
Poolside Truman Annex 2 Bed | Conch Life Condo
$361 per night
Superhost
Apartment in Key West
The Bartlum by Brightwild | Luxurious Studio
$316 per night
Superhost
Apartment in Key West
Duval Balcony - Street Suite
$260 per night
Superhost
Apartment in Key West
KW Luxury 2/2 Beachfront resort Tropical Oasis
$411 per night
Superhost
Apartment in Key West
#201 Key West Suites
$279 per night
Superhost
Apartment in Key West
Island Color Suite
$452 per night
Superhost
Apartment in Key West
Duval Street Suites full kitchen, parking, pool
$340 per night
Superhost
Apartment in Key West
Clean Apartment Key West (Best Downtown Locations)
$269 per night
Superhost
Apartment in Key West
Historic First Floor Caroline St w/Pool Sleeps 3
$125 per night
Superhost
Apartment in Key West
Comfy 2/2 pool/gym/tennis/hottub
$284 per night

Key West condo rentals

Superhost
Condo in Key West
Large 2/2 Waterfront Condo Great View Pool & Dock
$156 per night
Superhost
Condo in Key West
A Perfect Getaway
$311 per night
Superhost
Condo in Key Colony Beach
Oceanfront Breeze Condo Stunning Views, Beach/Pool
$255 per night
Superhost
Condo in Key West
La Dolce Vita, Old Town Steps to Duval! 3 blks bch
$305 per night
Superhost
Condo in Key West
Anchor Drop modern elegance upgrades throughout vi
$384 per night
Superhost
Condo in Key West
Beach Club Ocean Front 2BR Condo
$429 per night
Superhost
Condo in Key Colony Beach
Beachside Unit 39 Tiki Huts, Private Beach & Pool
$253 per night
Superhost
Condo in Key West
Ocean Front Studio private Sandy Beach in Key West
$133 per night
Superhost
Condo in Key West
Hidden Beach unit 2, The Perfect Place To Stay
$625 per night
Superhost
Condo in Key West
*Come to my Deck for a time you won't Forget!
$261 per night
Superhost
Condo in Key West
The Island Suite @ KW vacation
$356 per night
Superhost
Condo in Key West
Bright Condo in Paradise
$400 per night

Quick stats about vacation rentals in Key West

Total rentals

1.7K properties

Rentals with a pool

1.2K properties have a pool

Pet-friendly rentals

470 properties allow pets

Family-friendly rentals

1.1K properties are a good fit for families

Total number of reviews

48K 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 500 house rentals, over 410 condo rentals to over 270 apartment rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

  • How much does it cost to stay in vacation home rentals in Key West?

    Experience the best of Key West with our vacation home rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Key West