Key West holiday homes

We found 2,337 holiday rentals — enter your dates for availability

Select from 1107 houses, 275 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:19 Dec - 26 Dec
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Why visit Key West

  • Stunning beaches: Key West boasts beautiful beaches perfect for sunbathing and water activities, making it a great spot for relaxation.
  • Cultural attractions: Explore historic houses and museums that showcase the rich history and vibrant culture of this island city.
  • Vibrant nightlife: Experience lively nightlife with bars, live music, and entertainment that cater to all tastes.
  • Outdoor adventures: Enjoy tropical excursions and natural beauty in nearby national parks, ideal for nature lovers.
  • Unique charm: Key West's blend of relaxation and excitement creates a distinctive atmosphere, perfect for any holiday.

Top attractions in Key West

Key West is a fantastic spot for families and business travellers alike, offering a mix of culture and outdoor experiences. You can explore stunning beaches, visit historic houses, and enjoy the natural beauty of nearby national parks. Whether you’re after sun-soaked relaxation or cultural immersion, Key West has something for everyone. Don’t miss out on the unique charm and attractions this vibrant destination has to offer.

  • Duval Street: A lively thoroughfare brimming with vibrant nightlife, eclectic shops, and charming cafes. It's the heart of Key West, where you can soak up the local atmosphere while enjoying street performers and lively bars.
  • Smathers Beach: This expansive, sandy beach offers a quintessential tropical experience with crystal-clear waters. Perfect for sunbathing, swimming, and beach games, it’s a fantastic spot to unwind and soak up the sun.
  • Ernest Hemingway Home and Museum: Explore the former residence of the iconic author, rich in history and culture. Wander through lush gardens and admire the unique architecture while learning about Hemingway’s life and works.

Things to do recommended for couples

Planning a romantic getaway to Key West? Enjoy a sunset sail on a catamaran, explore the charming streets hand-in-hand, or indulge in fresh seafood at a waterfront restaurant. Don't miss the breathtaking sunset at Mallory Square—it's the perfect cap to a lovely day together.

Things to do recommended for families

In Key West, families can splash around at the MLK Community Pool & Community Center, which offers a vibrant atmosphere perfect for sports and outdoor fun. It's a great spot for kids to make new friends while enjoying the sunny Florida weather.

Things to do recommended for groups

Experience the vibrant culture at the Red Barn Theater, enjoy unique finds at The Kite House, or challenge your mates at the Key West Golf Club for some outdoor fun. Each spot promises an unforgettable time for your group in this beautiful island paradise.

*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

When you're planning a trip—whether it's with a group, your family, or even your furry friends, and if you're considering longer stays—be sure to filter according to your key preferences. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Key West with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group get-togethers. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Key West with young kids: Travelling with young kids can be quite tricky. It’s important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Key West: For many, a family holiday isn’t truly complete without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly listings come equipped with feeding bowls and bedding, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Key West: If you're in search of holiday rentals offering great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on long-term rentals. Don't forget to include extras like a car park, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay in Key West

Key West, a stunning island city in Florida, offers an unforgettable vacation experience for families, couples, and business travellers alike. Explore the vibrant nightlife, indulge in tropical excursions, and unwind in the serene atmosphere of nearby Key Largo. Whether you're after a romantic getaway or an action-packed Florida adventure, Key West promises a unique blend of relaxation and excitement, making it the perfect destination for your next holiday.

  • Old Town Key West: Old Town Key West is a vibrant neighbourhood that serves as the heart of the island. Known for its charming streets and historic architecture, it provides a delightful mix of shopping, dining, and entertainment. Visitors can enjoy the lively atmosphere while exploring local boutiques and galleries. The area is also home to stunning beaches, perfect for families looking to relax by the water. Whether you're wandering through the local markets or soaking up the sun on the beach, Old Town Key West offers a unique blend of urban charm and coastal beauty.
  • Stock Island: Just a short drive from Key West, Stock Island is a hidden gem with a laid-back vibe and natural beauty. This island is perfect for those seeking outdoor adventures, with plenty of opportunities for fishing, boating, and exploring picturesque marinas. Families can enjoy the local beaches and parks, making it an ideal spot for a relaxed day out. Stock Island also features a variety of dining options, showcasing fresh seafood and local flavours. It's a great destination for travellers who want to experience the quieter side of the Keys while still being close to the action.
  • Key West Historic District: The Key West Historic District is a must-visit for history buffs and culture lovers. This area is rich in heritage, with beautifully preserved buildings and landmarks that reflect the island's storied past. Visitors can stroll along the cobblestone streets, enjoying the local shops and cafés that line the way. Beach access is nearby, providing a lovely spot for families to enjoy water activities. The district offers a family-friendly atmosphere combined with a strong sense of community, making it a lovely place to explore and unwind.

Booking with Vrbo is simple

Are you eager to save some cash on your upcoming adventure? A little flexibility with your travel dates can go a long way, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, make use of our filters to sort by price, location, and type of holiday rental. We're here to help you find the best options for your next getaway.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a handy way to plan your next adventures, allowing you to easily create new trips, resume your previous planning, or review and manage your itineraries. You'll be able to see your saved or booked properties sorted into categories: Potential, Upcoming, and Current Trips. To begin using Trip Boards, simply 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. 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.

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