Key West holiday rentals

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Best Key West holiday rentals

Most recommended holiday rentals in Key West

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Colors On White - Key West - Bedroom
Colors On White
7.4 Good
Old Town North of Truman£369+
£369+
Parking
Free Wi-Fi
Pool
Pet-friendly
Coral Cove - Key West - Pool
Coral Cove
8.6 Very Good
Old Town South of Truman£335+
£335+
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Pescado Penthouse
7.9 Good
Old Town South of Truman£1,664+
£1,664+
Free Wi-Fi
Pet-friendly
Air conditioning
Curry House - Room 9
6.4 Okay
Old Town North of Truman£432+
£432+
Free Wi-Fi
Pool
Air conditioning
Key West Villas
9.7 Wonderful
Old Town North of Truman£582+
£582+
Free Wi-Fi
Pool
Air conditioning
Honey Bun Hideaway
8.5 Very Good
Old Town North of Truman£537+
£537+
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Rose Lane Villas
8.6 Very Good
Old Town North of Truman£635+
£635+
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Truman
8.2 Very Good
Old Town North of Truman£459+
£459+
Free Wi-Fi
Air conditioning
Truman @ Duval
7.9 Good
Old Town North of Truman£478+
£478+
Free Wi-Fi
Air conditioning
Sunrise Suites Cozumel Suite #112
7.8 Good
New Town£547+
£547+
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Carey's Corner #10 By Brightwild
8.8 Very Good
Old Town South of Truman£259+
£259+
Pool
Air conditioning

Good to know

Low season

December

High season

February

Average price (weeknight)

£231
Cheapest month to stay with an average 23% drop in price.
Most expensive month to stay with an average 34% rise in price.
Average Sun - Thu price over the last 2 weeks.

When to book a holiday rental in Key West

Price per night / rental. Prices are not fixed and may vary with time.
Average nightly price per month
Average nightly price

Top tips for finding Key West holiday 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 no minors are the most popular holiday rental property amenities in Key West
  • Holiday rentals in Key West are around 34% more expensive than hotels on average. Search here to compare prices for all accommodation types in Key West.
  • The best holiday 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, 31), and Key West Villas (9.7, 559), based on ratings and reviews from real travellers.
  • Mid Town East is the neighbourhood in Key West with the most affordable holiday rental properties (52 properties with an average price of £409 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.
  • Book your Key West holiday rental at least 16 days before your stay begins to get the best price.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Key West for 5 days.
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FAQs when booking a holiday home in Key West

  • How much is a holiday rental for a week in Key West?

    The average price for a weekly Key West holiday rental found by KAYAK users in the last 2 weeks is £5,077.

  • How much is a holiday rental for a month in Key West?

    The average price for a monthly Key West holiday rental found by KAYAK users in the last 2 weeks is £21,760.

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

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

  • What are the most popular Key West holiday rentals for a large group?

    If you’re a large group then you’ll need plenty of space. The highest rated holiday home that can sleep 6 people or more by KAYAK users is Sunrise Suites Resort.

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

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

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

    In the last 72 hours, users have found Key West holiday rentals for tonight for as low as £379. Search here for similar prices

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

    In the last 72 hours, users have found Key West holiday rentals for this weekend for as low as £508 per night. Search here for similar prices

  • Which are the most popular neighbourhoods to stay in Key West?

    Holiday 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 neighbourhoods, check out our Key West's City Guide.

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

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

  • How much is a holiday rental in Key West?

    KAYAK users have found holiday rentals in Key West for as cheap as £369 in the last 3 days. The average price is £725.

  • 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 holiday rental.

What Key West holiday rental guests are talking about

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Holiday rentals by topic

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Old Town Suites - Key West
Old Town Suites
8.1 Very Good
Old Town North of Truman£460+
£460+
Parking
Latitude Penthouse Key West - Key West
Latitude Penthouse Key West
8.7 Very Good
Mid Town West£849+
£849+
Parking

Popular topics

Everything you need to know for your stay in Key West

Hotels near airports in Key West

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

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