Key West holiday homes

We found 2,309 holiday rentals — enter your dates for availability
Select from 997 houses, 289 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.

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Why visit Key West

  • Historic Attractions: Visit the iconic Ernest Hemingway Home and explore the rich literary history of the island.
  • Vibrant Duval Street: Stroll along Duval Street, lined with lively bars, shops, and restaurants, showcasing the local culture.
  • Stunning Sunsets: Enjoy breathtaking sunsets at Mallory Square, a must-see experience for all visitors.
  • Beautiful Beaches: Relax on gorgeous beaches with crystal-clear waters, perfect for swimming and sunbathing.
  • Outdoor Adventures: Discover local national parks and engage in water sports, from snorkelling to kayaking.

Top attractions in Key West

Key West offers a blend of cultural, beach, and outdoor experiences ideal for family, city, and business holidays. Wander through historic houses, relax at nearby beaches, and explore the local national and state parks. This vibrant city provides a unique mix of attractions, ensuring a memorable holiday filled with exploration and relaxation in a setting that caters perfectly to diverse interests.

  • Duval Street: Experience vibrant city vibes with lively bars, unique local shops, and a blend of cultural heritage all in a colourful urban setting.
  • Smathers Beach: Enjoy expansive sandy shores, gentle ocean waves, and a relaxed beach atmosphere perfect for sunbathing and water-based activities.
  • Fort Zachary Taylor Historic State Park: Discover outdoor adventures with lush surroundings, historical fort explorations, and scenic seaside views ideal for picnics and leisurely strolls.

Things to do recommended for couples

For a romantic getaway in Key West, indulge in sunset sailing on a catamaran, explore the charming streets on a bicycle, or enjoy a candlelit dinner at a waterfront restaurant. Don't forget to visit the iconic Mallory Square for stunning sunset views together.

Things to do recommended for families

Families visiting Key West can experience the vibrant marine life at the Key West Aquarium and enjoy a day of adventure at the Dry Tortugas National Park, where kids can explore historic forts and snorkel in crystal-clear waters.

Things to do recommended for groups

Explore the vibrant streets of Old Town, visit the Ernest Hemingway Home and Museum, or take a sunset sail with your mates. Don’t miss the lively atmosphere at Mallory Square and indulge in fresh seafood at local eateries for a true taste of Key West.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Key West

Whether you're travelling in a group, with your whanau, bringing your pets along or planning a longer stay, be sure to use the appropriate filters. Here are some Vrbo booking tips for you.

  • Traveling to Key West with a group: Consider how many bedrooms you'll require, along with features like a fully-equipped kitchen or an outdoor area for group gatherings. Luckily, you can filter for all these options—and more—on Vrbo.
  • Traveling to Key West with young kids: Traveling with young kids can be demanding. It's important to prioritise their comfort and safety, as well as ensuring there are age-appropriate facilities, like a private swimming pool. It's also wise to think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Key West: For many, a family holiday simply isn’t complete without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations include feeding bowls and beds, ensuring that every member of the family feels right at home.
  • Planning for a long term stay visiting Key West: If you’re searching for holiday rentals offering deals for month-long stays, you’ve come to the right spot. With the proper filter, you can effortlessly find and save on monthly rentals. You might also want to consider including a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in Key West

Key West, Florida, is a vibrant island city that offers an unforgettable getaway for families and couples alike. With its stunning sunsets, charming streets, and rich history, visitors can explore attractions such as the iconic Ernest Hemingway Home, the lively Duval Street, and the serene beaches. Enjoy excursions that showcase the tropical beauty and laid-back atmosphere, making Key West a perfect destination for relaxation and adventure in the heart of the Florida Keys.

  • Old Town Key West: Nestled in the heart of Key West, Old Town Key West is a charming neighbourhood that invites visitors to immerse themselves in a blend of cultural and recreational experiences. Its streets are lined with boutique shopping areas and a bustling shopping mall centre, perfect for those who relish a vibrant urban scene. The local attractions include a scenic street and a family-friendly beach, making it an ideal destination for travellers seeking a mix of city-themed and family-oriented activities.
  • Stock Island: Situated in the vicinity of Key West, Stock Island offers a unique island escape combined with a lively urban spirit. This naturally featured island is renowned for its blend of family-friendly and city-themed experiences, with a strong business vibe. Here, you can enjoy leisurely strolls through shopping areas and mall centres or tee off at a nearby golf course. The island's landmarks, including its beach and a family-friendly shoreline, provide a picturesque backdrop for a relaxing holiday.
  • Key West Historic District: Rich in heritage and charm, the Key West Historic District is a neighbourhood that captures the essence of the area’s storied past. It offers a diverse range of experiences, from vibrant shopping areas and mall centres to a serene resort atmosphere. Travellers can explore nearby streets and enjoy a family-friendly beach, making it a delightful destination for those interested in city-themed, family, and business-oriented adventures.

Booking with Vrbo is simple

If you’re keen to stretch your travel budget further, consider being flexible with your dates, as pricing can change. You might also enjoy considerable savings by opting for a longer stay. To easily find a Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board provides a helpful space for you to plan new adventures, continue with your arrangements, or manage your bookings with ease. Your saved or booked properties are conveniently organised into Potential, Upcoming, or Current Trips. To check out Trip Boards, head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

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. Take in top local attractions such as Duval Street and Southernmost Point. 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)
  • The Kite House (0.3 mi / 0.5 km)
  • Blue Hole (28.6 mi / 46.1 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:

  • Southernmost Point (0.6 mi / 1 km)
  • Florida Keys Beaches (16 mi / 25.8 km)
  • Key West Butterfly and Nature Conservatory (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.

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