Key West holiday homes

We found 2,350 holiday rentals — enter your dates for availability

Select from 1351 houses, 264 apartments and other holiday rentals to find the perfect place for your stay in Key West. Whether you’re staying in a holiday home with a group or just with your pet, you'll have the amenities that you expect and more, which might include air conditioning and a pool. No matter what you're looking for, you'll be sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Key West

Showing deals for:3 Oct - 10 Oct

Image gallery for Living the Dream Key West Style

Marina
10 out of 10 rating
Exceptional
(19 reviews)

Living the Dream Key West Style

Key West, FL

8% off
Price is NZ$3,780
NZ$540 per night
includes taxes & fees
Living the Dream Key West Style

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Take in the picturesque beauty of Key West

The area's live music and festivals are just some of the reasons to come on holiday to Key West. This city's bars, seaside and boating draw many visitors. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Key West

Are you hoping to find attractions to see while you're in town? Travellers enjoy fun activities like boating and cycling. Venture out of your cosy holiday rental and experience everything that makes Key West a one-of-a-kind holiday spot. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Key West Golf Club (4 mi / 6.5 km)
  • Blue Hole (28.6 mi / 46.1 km)
  • The Kite House (0.3 mi / 0.5 km)
  • MLK Community Pool & Community Center (0.5 mi / 0.8 km)

Exploring the natural landscape of Key West

Travellers love Key West for its breathtaking sunsets and beautiful ocean views. Whether you're looking for adventure or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Key West. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Audubon House and Tropical Gardens (0.3 mi / 0.6 km)
  • Key West Butterfly and Nature Conservatory (0.6 mi / 1 km)
  • Southernmost Point (0.6 mi / 1 km)
  • South Beach (0.7 mi / 1.1 km)
  • Simonton Beach (0.8 mi / 1.2 km)
  • Truman Beach (0.9 mi / 1.4 km)

Transport to and around Key West

Fly into Key West, FL (EYW-Key West Intl.), the closest airport, located 3 mi (4.8 km) from the city centre.

Frequently asked questions

What is the best area to stay in Key West when booking a holiday home?
Snap up your holiday property in Key West Historic District and you'll be in the heart of one of Key West's leading neighbourhoods. Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens are two major attractions here that'll entertain you during your visit.
What is the most popular type of holiday home accommodation in Key West?
Based on our research, houses are the most desirable property type in Key West. But naturally, everyone's idea of the perfect stay differs. Bookabach has holiday homes of all shapes and sizes, and we'll help you to find your perfect match.
How much does it cost to rent a holiday home in Key West?
Length of stay, property type and season are some of the things that can influence the price of a holiday home. Simply enter your dates of travel to find your perfect fit. From cosy chalets to expansive villas, all Bookabach holiday homes offer incredible value.
How much does it cost to rent a beach house in Key West?
When you travel and the style and size of the property will influence the cost of your beachside stay. Put in your Key West travel dates to see all your options on Bookabach. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use our filters to choose the amenities and features you want in your beach house.
Are there pet-friendly holiday homes in Key West?
Yes. You can pick from 1,825 holiday homes that cater to pets in Key West. Lots of our pet-friendly holiday homes even come with an outdoor area for your four-legged friend to play around in, doggie beds, complimentary treats and proximity to parks or green space. Apply the "Pets allowed" filter to find your pawfect place on Bookabach.
Can I rent a house with a pool in Key West?
Mark the "pool" box in our filter tool and take your pick of 1,496 houses with private pools in Key West on Bookabach. Morning swim, sunset soak or midnight dip? How you spend your free time is up to you when your Bookabach holiday property boasts a swimming pool.
What are popular home amenities in Key West?
Some of the most popular home amenities people are searching for in Key West include mountain views, a lake view and a barbecue grill. Whether you're on the road with buddies, family or even pets, Bookabach holiday properties have the best amenities for chilling out with your loved ones.
Are there large group holiday homes in Key West?
You can pick from 191 holiday properties in Key West that can host a group of 10 or more guests. Whether you're organising time away with the family or an event like an anniversary, there's enough room to get your loved ones together under the same roof.
Are there holiday homes in Key West that welcome kids?
Bring the entire group together for a fun-filled adventure in Key West at one of our 1,818 family-friendly holiday properties. Many of these stays offer amenities that are suitable for getaways with the kids, such as full kitchens, extra bedrooms and pools. Just check the "Properties good for families" filter box and choose your favourite.
What are the top attractions for families in Key West?
There are loads of amazing things to see and do with the family in Key West, including:

  • Smathers Beach
  • South Beach
  • Higgs Beach

Are there one-bedroom holiday homes in Key West?
You can choose from 451 one-bedroom homes in Key West. Whether you're searching for a townhouse or a cabin, our one-bedroom properties are just right if you don't require loads of space. One of the perks of having your own digs? You'll never need to share your holiday with strangers.
Can I find two-bedroom holiday homes in Key West?
Take your pick of 670 two-bedroom holiday homes in Key West. Settle the kids into the second room or fill it with a couple of your besties. There's a spot for whoever's fortunate enough to be coming along.
Are there holiday homes with WiFi in Key West?
You can choose from 568 holiday homes with WiFi in Key West. If you'd like to disconnect from the world while on holiday, but still need to be connected to the web, these properties are for you. Narrow your search by applying the WiFi filter on Bookabach.
How can I find holiday homes with air conditioning in Key West?
Key West has 1,762 holiday homes where you can unwind in air-conditioned comfort. To book a stay on Bookabach offering this perk, enter your travel dates and use the handy filters to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Key West?
The minimum age is usually 16, 18 or 21. It can change between properties on Bookabach, so check the rules of your chosen Key West holiday home before you book.
How long can I rent a holiday home in Key West for?
How long you can book a holiday home in Key West is down to the property. Just enter your preferred dates to display a list of options offering extended stays. With a range of creature comforts like kitchens and air conditioning, as well as some offering weekly or monthly discounts, you're sure to get somewhere just right to call your home away from home in Key West.

Explore destinations around Key West

Key West Butterfly and Nature Conservatory (2,336)
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Red Barn Theater (2,432)
Standard link for Red Barn Theater
Key West Art and Historical Society (2,769)
Standard link for Key West Art and Historical Society
Ernest Hemingway Home and Museum (2,432)
Standard link for Ernest Hemingway Home and Museum
Sails To Rails Museum at Flagler Station (2,432)
Standard link for Sails To Rails Museum at Flagler Station
Nancy Forrester's Secret Garden (2,432)
Standard link for Nancy Forrester's Secret Garden
Studios of Key West (2,434)
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San Carlos Institute - Casa Cuba (2,432)
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Custom House Museum (2,431)
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The Kite House (2,432)
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Heritage House Museum (2,431)
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Museum of Art & History at the Custom House (2,431)
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Oldest House Museum and Garden (2,432)
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Key West Aquarium (2,431)
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Curry Mansion Museum (2,432)
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Key West Shipwreck Museum (2,431)
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Key West Lighthouse and Keeper's Quarters Museum (2,432)
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Mel Fisher Maritime Museum (2,431)
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Florida Keys Eco - Discovery Center (2,425)
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Roy John-Karl Gallery (2,431)
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