Key West holiday lettings

We found 2,349 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

Why visit Key West

  • Stunning beaches: Key West boasts beautiful sandy shores, perfect for relaxation and sunbathing.
  • Rich cultural heritage: Explore historic houses and museums that showcase the island's unique history.
  • Outdoor activities: Engage in a variety of adventures such as snorkelling, fishing, and kayaking in crystal-clear waters.
  • Charming neighbourhoods: Wander through vibrant streets filled with local shops, cafes, and art galleries.
  • Varied accommodation options: Choose from quaint cottages to modern condos, catering to all tastes and budgets.

Popular types of accommodation in Key West

Planning a getaway to Key West? The next step is selecting the perfect accommodation. From charming cottages to spacious private homes and modern condos, there’s a range of holiday rentals to suit every taste and budget. Discover the ideal house rental for your stay and enjoy the comforts of home while exploring the vibrant atmosphere of this tropical paradise.

  • Houses: The top choice for holidaymakers in Key West, offering spacious and comfortable living for families, couples, or groups of friends.
  • Condos: A favoured option for many, providing a blend of convenience and luxury, often with stunning views and shared amenities.
  • Cottages: Charming and quaint, these retreats offer a cosy atmosphere, perfect for a romantic getaway or a peaceful escape.
  • Apartments: Ideal for those seeking a home-from-home experience, with self-catering facilities and a central location.
  • Villas: Elegant and spacious, these upscale properties cater to those looking for a more lavish stay in Key West.**

Top attractions in Key West

Key West is an ideal destination for families, business travellers, and those seeking a city-themed holiday. With its stunning beaches, captivating national parks, and historic houses, visitors can indulge in a rich cultural experience while enjoying outdoor activities. Whether you're after relaxation or adventure, Key West offers a variety of attractions to suit every traveller's needs.

  • Duval Street: A vibrant hub of activity, Duval Street is lined with eclectic shops, lively bars, and delightful eateries. Experience the energetic atmosphere as you stroll along this historic thoroughfare, where street performers and local artists add to the charm.
  • Mallory Square: Famous for its spectacular sunsets, Mallory Square is a bustling gathering place where you can enjoy street performances, artisan stalls, and stunning views of the Gulf of Mexico. It's the perfect spot to unwind and soak in the local culture.
  • Smathers Beach: Offering a picturesque slice of paradise, Smathers Beach boasts soft sands and crystal-clear waters. Relax under a palm tree, partake in water sports, or enjoy a leisurely stroll along the shoreline, soaking up the sun and sea breeze.

Things to do recommended for couples

Seeking a romantic getaway in Key West? Enjoy a leisurely sunset sail on a catamaran or take a stroll along the picturesque Duval Street, soaking in the vibrant atmosphere. Don't forget to share a slice of key lime pie while watching the sunset at Mallory Square.

Things to do recommended for families

Families visiting Key West can have a splendid day at the MLK Community Pool & Community Center, where they can enjoy the outdoor pool and partake in various sports activities, all while soaking up the friendly family atmosphere of this vibrant local spot.

Things to do recommended for groups

Enjoy a round of golf at the Key West Golf Club, embrace the vibrant culture at the Waterfront Playhouse, and explore unique finds at The Kite House. These local experiences promise to create unforgettable memories for your group in the sunny paradise of Key West.

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming holiday? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday accommodation.

Where to stay in Key West

Key West offers a delightful island getaway, perfect for families and couples alike. With its vibrant atmosphere, visitors can explore charming neighbourhoods, indulge in tropical excursions, and soak up the romantic vibe of this unique city. Whether you're seeking relaxation or adventure, Key West is a splendid destination to create unforgettable memories, making it an ideal choice for your next holiday.

  • Old Town Key West: Old Town Key West is a vibrant neighbourhood steeped in history and charm. Located in the heart of Key West, it offers a delightful blend of city-themed experiences, family-friendly activities, and business opportunities. Stroll through its picturesque streets lined with colourful architecture, explore local shops and boutiques, and relax at nearby family beaches. Notable attractions include the lively shopping area and various resorts, making it an ideal spot for both leisure and business travellers.
  • Key West Historic District: The Key West Historic District is a captivating area that draws visitors with its rich heritage and unique atmosphere. Nestled within Key West, this district is perfect for families and city explorers alike. With an array of shopping areas, malls, and charming resorts, it caters to diverse interests. Wander through historic streets, enjoy the local beach scene, and immerse yourself in the vibrant culture of the island. The district's attractions make it a must-visit for anyone seeking a blend of history and modern conveniences.
  • New Town: New Town offers a contemporary twist to the traditional Key West experience. Located close to the main attractions, it’s an excellent choice for families and business travellers. This neighbourhood features bustling shopping areas, modern malls, and comfortable resorts, ensuring visitors have all they need for a fantastic stay. The proximity to beautiful beaches and scenic streets makes it a great launchpad for exploring the rest of the island. Whether you’re seeking relaxation or adventure, New Town has something for everyone.

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

If you’re travelling with a group, family, pets, or planning an extended stay, it’s essential to filter your options based on your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Key West with a group: Think about how many bedrooms you'll require, as well as additional features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Key West with young kids: Travelling with young children can indeed be quite demanding. It's essential to prioritise their comfort and safety, alongside ensuring that there are suitable amenities for their age, such as 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 families, a holiday wouldn’t feel complete without their furry companions. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Key West: If you're in search of holiday rentals with special offers for stays of a month or more, you've come to the perfect place. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform for you to plan new adventures, resume your previous arrangements, or simply manage your travel itinerary. Here, you can easily find the properties you’ve saved or booked, organised under Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.vrbo.com/en-gb/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 rental?
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 rental 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. Vrbo 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 rental 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 Vrbo holiday rentals 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 Vrbo. 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 rentals in Key West?
Yes. You can pick from 1,825 holiday rentals that cater to pets in Key West. Lots of our pet-friendly holiday rentals 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 Vrbo.
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 Vrbo. Morning swim, sunset soak or midnight dip? How you spend your free time is up to you when your Vrbo holiday property boasts a swimming pool.
What are popular rental amenities in Key West?
Some of the most popular rental 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, Vrbo holiday properties have the best amenities for chilling out with your loved ones.
Are there large group holiday rentals 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 rentals 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 rentals in Key West?
You can choose from 451 one-bedroom rentals 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 rentals in Key West?
Take your pick of 670 two-bedroom holiday rentals 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 rentals with WiFi in Key West?
You can choose from 568 holiday rentals 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 Vrbo.
How can I find holiday rentals with air conditioning in Key West?
Key West has 1,762 holiday rentals where you can unwind in air-conditioned comfort. To book a stay on Vrbo 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 rental in Key West?
The minimum age is usually 16, 18 or 21. It can change between properties on Vrbo, so check the rules of your chosen Key West holiday rental before you book.
How long can I rent a holiday rental in Key West for?
How long you can book a holiday rental 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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