Key West vacation rentals

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Best Key West vacation rentals

Most recommended vacation rentals in Key West

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Old Town Suites - Key West - Living room
Old Town Suites
8.1 Very good
Old Town North of Truman₪2,089+
₪2,089+
Free Wi-Fi
Air Conditioning
Colors On White - Key West - Bedroom
Colors On White
7.5 Good
Old Town North of Truman₪1,188+
₪1,188+
Parking
Free Wi-Fi
Pool
Pet friendly
Carey's Corner #10 by Brightwild
9.1 Wonderful
Old Town South of Truman₪1,599+
₪1,599+
Free Wi-Fi
Pool
Pet friendly
Air Conditioning
Key West Villas
9.7 Wonderful
Old Town North of Truman₪1,742+
₪1,742+
Free Wi-Fi
Pool
Air Conditioning
Curry House by Brightwild- Room 9
6.3 Okay
Old Town North of Truman₪1,570+
₪1,570+
Free Wi-Fi
Pool
Air Conditioning
Pescado Penthouse On Duval
8.1 Very good
Old Town South of Truman₪1,342+
₪1,342+
Free Wi-Fi
Air Conditioning
Rose Lane Villas
8.7 Very good
Old Town North of Truman₪2,023+
₪2,023+
Free Wi-Fi
Pool
Pet friendly
Air Conditioning
Truman
7.1 Good
Old Town North of Truman₪1,622+
₪1,622+
Free Wi-Fi
Air Conditioning
Palm Gardens
The Meadows₪1,476+
₪1,476+
Free Wi-Fi
Southernmost Sanctuary
7.4 Good
Old Town South of Truman₪2,157+
₪2,157+
Free Wi-Fi
Air Conditioning
Court Cottages
7.8 Good
Old Town North of Truman₪1,631+
₪1,631+
Free Wi-Fi
Air Conditioning
Matisse Manor #5
Old Town South of Truman₪1,359+
₪1,359+
Pool
Air Conditioning
Sunrise Suites Cozumel Suite #112
8.3 Very good
New Town₪1,713+
₪1,713+
Free Wi-Fi
Pool
Air Conditioning
Truman @ Duval
8.6 Very good
Old Town North of Truman₪1,614+
₪1,614+
Free Wi-Fi
Air Conditioning
Papa's Hideaway
Old Town South of Truman₪1,855+
₪1,855+
Free Wi-Fi
Pool
Air Conditioning

Good to know

Low season

December

High season

February

Average price (weeknight)

₪1,635

Average price (weekend night)

₪2,281
Cheapest month to stay with an average 36% drop in price.
Most expensive month to stay with an average 26% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

When to book a vacation 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 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.
  • Pool and 24 hour front desk are the most popular vacation rental property amenities in Key West
  • Vacation rentals in Key West are around 28% 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 (10.0, 39 reviews), Claro ~ Adults Only, Poolview 1 Br, 1 Ba Suite In Azul Mansion! (9.8, 62), and Key West Villas (9.7, 338), based on ratings and reviews from real travelers.
  • Mid Town East is the neighborhood in Key West with the most affordable vacation rental properties (50 properties with an average price of ₪1,257 per night). By The Beautiful Sea, Brisa Del Mar by AvantStay Communal Pool Gated Community Ocean Front, and Happys Houseboat Key West are the most popular rental properties in Mid Town East.
  • If you’re looking for a cheap vacation rental in Key West, you should consider visiting during the low season. The cheapest vacation homes in Key West can be found in October and August.
  • The cheapest night for renting a vacation home in Key West is Wednesday. In contrast, the most expensive is Saturday.
  • Book your Key West holiday rental at least 5 days before your stay begins to get the best price.
  • 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.

FAQs when booking a vacation home in Key West

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

    The average price for a weekly Key West vacation rental found by KAYAK users in the last 2 weeks is ₪17,560.

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

    The average price for a monthly Key West vacation rental found by KAYAK users in the last 2 weeks is ₪75,255.

  • 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 villas, condos, houses and apartments.

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

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

  • 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 14% allowing you to bring your pet along with you.

  • How much is a vacation rental in Key West?

    KAYAK users have found vacation rentals in Key West for as cheap as ₪1,149 in the last 3 days. The average price is ₪2,509.

  • 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 ₪1,793. 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.

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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What Key West vacation rental guests are talking about

Vacation rentals by topic

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Poolside Paradise by Brightwild - Key West
Poolside Paradise by Brightwild
8 Very good
Old Town North of Truman₪6,337+
₪6,337+
Parking
Latitude Penthouse Key West - Key West
Latitude Penthouse Key West
8.9 Very good
Mid Town West₪2,891+
₪2,891+
Parking
Bananas Foster Guesthouse by Brightwild
10 Wonderful
Old Town North of Truman₪16,240+
₪16,240+
Parking
Somewhere on the beach
9.9 Wonderful
Mid Town West₪3,094+
₪3,094+
Parking

Popular topics

Landmarks in Key West