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Key West vacation rentals

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Best Key West vacation rentals

Most recommended vacation rentals in Key West

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Colors On White - Key West - Bedroom
Colors On White
Old Town North of Truman
7.4Good(427)
Parking
Free Wi-Fi
Pool
Pet friendly
₪1,037+
Check availability
Hyatt Residence Club Key West, Sunset Harbor - Key West - Building
Hyatt Residence Club Key West, Sunset Harbor
Truman Annex
7.5Good(99)
Free Wi-Fi
Pool
Air Conditioning
₪1,440+
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Curry House - Room 9 - Key West - Balcony
Curry House - Room 9
Old Town North of Truman
5.8Fair(20)
Free Wi-Fi
Pool
Air Conditioning
₪1,178+
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Pescado Penthouse - Key West - Bedroom
Pescado Penthouse
Old Town South of Truman
7.9Good(46)
Free Wi-Fi
Pet friendly
Air Conditioning
₪3,623+
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Heart of Old Town getaway, perfect romantic retreat - near the action - Key West - Beach
Heart of Old Town getaway, perfect romantic retreat - near the action
Old Town North of Truman
9.1Wonderful(24)
Air Conditioning
₪1,664+
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Key West Villas - Key West - Front desk
Key West Villas
Old Town North of Truman
9.7Wonderful(575)
Free Wi-Fi
Pool
Air Conditioning
₪1,584+
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Fontana ~ Adults Only, Pool Access King Room At Azul Mansion! - Key West - Living room
Fontana ~ Adults Only, Pool Access King Room At Azul Mansion!
Old Town North of Truman
Free Wi-Fi
Air Conditioning
₪1,392+
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Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC - Key West - Outdoors view
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC
Old Town North of Truman
Free Wi-Fi
Air Conditioning
₪1,227+
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Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St. \n - Key West - Beach
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St. \n
New Town
Free Wi-Fi
Pool
Air Conditioning
₪2,048+
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Curry House - Pool, King Bed & Balcony! Room 7 - Key West - Balcony
Curry House - Pool, King Bed & Balcony! Room 7
Old Town North of Truman
7.7Good(14)
Free Wi-Fi
Pool
Air Conditioning
₪1,542+
Check availability
Flor De Cana ~ Adults Only, Poolview Queen Room At Azul Mansion! - Key West - Living room
Flor De Cana ~ Adults Only, Poolview Queen Room At Azul Mansion!
Old Town North of Truman
Free Wi-Fi
Air Conditioning
₪1,450+
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Curry House Room 6 - Key West - Restaurant
Curry House Room 6
Old Town North of Truman
7.8Good(13)
Free Wi-Fi
Pool
Air Conditioning
₪1,505+
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Sunny Condo with WiFi, Hot Tub, Pool & Tennis - Key West
Sunny Condo with WiFi, Hot Tub, Pool & Tennis
New Town
Free Wi-Fi
Air Conditioning
₪1,949+
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Coral Cove #1 By Brightwild - Key West
Coral Cove #1 By Brightwild
Old Town South of Truman
8.4Very good(24)
Pool
Air Conditioning
₪1,505+
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Rose Lane Villas - Key West
Rose Lane Villas
Old Town North of Truman
8.5Very good(483)
Free Wi-Fi
Pool
Pet friendly
Air Conditioning
₪1,974+
Check availability
Sunrise Suites Cozumel Suite #112 - Key West
Sunrise Suites Cozumel Suite #112
New Town
7.7Good(62)
Pool
Pet friendly
Air Conditioning
₪1,815+
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KAYAK’s insights for vacation rentals in Key West

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Key West with confidence.

Which month has the cheapest vacation rental rates in Key West?

Vacation rentals are cheapest in Key West in December, with average rates of ₪4,125. In comparison, November is the most expensive month, with prices at ₪10,508.

What is the cheapest day of the week to book a vacation rental in Key West?

Thursday offers the lowest rates in Key West, with an average nightly price of ₪4,463. The highest prices are found on Wednesday, with average rates at ₪6,234.

How early should you book a vacation rental in Key West?

Book at least 3 days before your stay begins to get the best price for your Key West vacation rental.
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KAYAK's top tips for finding Key West vacation rental deals

  • If you have pets, you'll enjoy staying close to Dog Beach, which is close to Peaceful, a dog-friendly home in a residential neighbourhood with a shared pool.
  • For those who are visiting for the history, a Key West holiday rental in Old Town is the best idea, as that’s where most of the iconic architecture and attractions are concentrated, with thousands of colourful wooden structures from the 1800s. Stay at a Key West holiday home like Aria or visit the seaport, or wander around vintage homes.
  • Key West rental homes in Old Town are also an excellent stay for weekend trips and those without a rental car, as it’s walkable to other neighbourhoods in minutes, and parking is in fact a challenge. Rose Lane Villas is just a five-minute walk from the Ernest Hemingway Home and Museum and Key West Aquarium.
  • For those looking for a few rounds of golf in the Florida sun, Key West holiday rentals in the aptly named Golf Club Area seems like an obvious choice. Floating Tiny Home will not only allow you to golf but also kayak right from your Key West house rental.
  • If you love beaches, try booking Key West holiday rentals in Casa Marina, like Tropical Village. You’ll be close to many of the island’s beaches: Smathers Beach, Higgs Beach, and Fort Zachary Taylor State Park Beach, as well as Southernmost Point, the southernmost point of continental US.
  • Pet friendly, beachfront, pool, air-conditioned, internet, and adults only are the most popular vacation rental property amenities in Key West
  • Vacation rentals in Key West are around 72% more expensive than hotels on average. Search here to compare prices for all accommodation types in Key West.
  • The best vacation rental properties in Key West are Studio Blue (9.9, 53 reviews), Casita de Catherine by AvantStay 1 Block to Duval St w Hot Tub (9.8, 32), and Key West Villas (9.7, 575), based on ratings and reviews from real travelers.
  • Mid Town East is the neighborhood in Key West with the most affordable vacation rental properties (58 properties with an average price of ₪1,323 per night). By the Beautiful Sea - Key West Beach Front Condo - w Pool Access, Happys Houseboat Key West, and Island Time Gorgeous Condo Steps To The Beach are the most popular rental properties in Mid Town East.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Key West for 1 days.
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FAQs when booking a vacation home in Key West

  • What types of vacation rentals are available in Key West?

    There are loads of different property types that you can make your vacation home in Key West. You’ll find apartments, boats, cabins, campgrounds, caravans, condos, cottages, houses, holiday parks, homestays, houseboats, lodges, recreational vehicles and villas.

  • Are there any pet-friendly vacation rentals in Key West?

    There are a number of dog and pet-friendly Key West vacation rentals, with around 16% allowing you to bring your pet along with you.

  • How much is a vacation rental in Key West for tonight?

    In the last 72 hours, users have found Key West vacation rentals for tonight for as low as ₪896. Search here for similar prices

  • How much is a vacation rental in Key West for this weekend?

    In the last 72 hours, users have found Key West vacation rentals for this weekend for as low as ₪2,290 per night. Search here for similar prices

  • What are the most popular Key West neighborhoods to book a vacation rental in?

    Vacation rentals in Old Town North of Truman, Truman Annex and Old Town South of Truman have the most searches on KAYAK. For more information about Key West's different neighborhoods, check out our Key West's City Guide.

  • How can I find vacation rentals near me in Key West?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

  • Which neighbourhood in Key West is recommended for those with a family?

    New Town is a great place to stay for those with families. It’s quieter and calmer, with plenty of shops to easily stock up on groceries. Bonus points for being close to Key West International Airport. Sunrise Suites - Great Exuma Suite #406 will comfortably accommodate a family of six.

  • Where does the nightlife of Key West happen?

    Duval Street is the most active area of the night in Key West, with bars, late-night restaurants and nightclubs and live music every night in many establishments. Charming, a dog-friendly home in a residential neighbourhood in Casa Marina, is steps away from Duval Street.

  • What is a safe area of Key West?

    A holiday rental in Truman Annex like Hyatt Residence Club Key West is as safe as it gets, as the neighbourhood is a private gated community. It is a longer walk to Duval Street and other attractions than other neighbourhoods, but it also boasts a museum that was a former residence of President Harry Truman.

  • Where can I do some shopping?

    New Town has contemporary shopping areas, but for an authentic Key West experience, you might like to stay in Newly Remodelled First Floor, to visit the popular flea market of Bahama Village.

  • Where can I find nice food?

    Bahama Village is lucky enough to also be one of the best areas for food, with Spanish tapas from Santiago's Bodega or brunch from the famous Blue Heaven. Decent food can also be had near the seaport of Old Town, with authentic Cuban food from Meson de Pepe’s, or seaside views at the Half Shell Raw Bar. Traveler's Palm is another accommodation in Bahama Village.

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Where to stay in Key West?

Our map will help you find the perfect place to stay in Key West by showing you the exact location of each vacation rental.

What Key West vacation rental guests are talking about

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Vacation rentals by topic

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Old Town Suites - Key West
Old Town Suites
Old Town North of Truman
8.1Very good(717)
Parking
₪1,361+
Check availability
Latitude Penthouse Key West - Key West
Latitude Penthouse Key West
Mid Town West
8.7Very good(38)
Parking
₪2,638+
Check availability
Hyatt Residence Club Key West, Windward Pointe - Key West
Hyatt Residence Club Key West, Windward Pointe
New Town
9.1Wonderful(1176)
Parking
₪1,612+
Check availability

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Key West vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Key West. Find cheap vacation homes to rent in Key West. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Key West that suits you best.

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