Key West holiday homes

We found 2,311 holiday rentals — enter your dates for availability
Select from 1025 houses, 265 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 Florida Keys Beaches. 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)

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:

  • Florida Keys Beaches (16 mi / 25.8 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?
In Key West, one of the best areas to consider for a holiday rental is the Old Town neighbourhood. This charming part of the island is renowned for its historic architecture and vibrant setting, making it a favourite among visitors. The streets are lined with colourful wooden houses, and you'll find a plethora of local shops, restaurants, and bars, all contributing to its lively character. Notable attractions in Old Town include the Ernest Hemingway Home and Museum, which offers a glimpse into the life of the famous author, and Mallory Square, known for its stunning sunset celebrations.Another appealing option is the area around the beach, particularly near Fort Zachary Taylor State Park. This area not only offers beautiful sandy beaches but also provides opportunities for swimming, snorkelling, and picnicking amidst lush surroundings. The park itself is a historical site featuring a Civil War-era fort, adding an educational twist to your beach day.While the exact number of properties in these neighbourhoods can fluctuate, Old Town typically boasts a wide array of rental options, from quaint guesthouses to luxurious villas.
Where are the best areas for renting a beach house in Key West?
For renting a beach house in Key West, the area around the Southernmost Point Buoy is particularly appealing, offering stunning ocean views and easy access to sandy beaches. Properties in this neighbourhood often come with amenities such as private pools, spacious outdoor decks, and well-equipped kitchens, making them ideal for families or groups looking to relax and enjoy the island lifestyle.Additionally, the historic district of Old Town is another excellent option, where charming conch-style homes are available for rent. Many of these properties feature inviting porches, lush gardens, and proximity to lively eateries and shops along Duval Street. Guests can expect modern conveniences alongside traditional architecture, with some rentals offering bicycles for exploring the local area.Further along the coastline, the area near Fort Zachary Taylor State Park provides beach houses that are just a stone's throw from the beach. These rentals often include amenities like beach gear, outdoor grills, and easy access to water sports, great for those looking to enjoy activities such as kayaking or paddleboarding. Find your rental near the beach in Key West.
Are there any houseboat rentals in Key West?
In Key West, houseboat rentals are quite popular, with around 220 options available throughout the area. These unique accommodations are often found in picturesque marinas or along the waterfront, providing stunning views and easy access to the ocean. Guests can expect amenities such as fully equipped kitchens, comfortable living spaces, and outdoor decks for enjoying the tropical climate. Many houseboats also come with additional features like BBQ grills, kayaks for exploring the surrounding waters, and air conditioning to ensure a comfortable stay. See all houseboats in Key West.
What is the most popular type of holiday rental accomodation in Key West?
In Key West, holiday houses are the most popular type of holiday rental, with approximately 3,952 available across the island. These spacious homes are often situated in charming neighbourhoods close to iconic attractions such as the Ernest Hemingway Home and Museum and the lively Duval Street. Most holiday houses come equipped with multiple bedrooms, fully fitted kitchens, and outdoor spaces like patios or pools, making them ideal for families or larger groups seeking comfort and convenience.Additionally, there are around 2,416 condos, which provide a more compact yet comfortable option. These typically include amenities like kitchenettes, communal pools, and easy access to the beach, appealing to couples and smaller groups who prefer a more modern living space.
Are there any family house rentals in Key West?
In Key West, there are numerous family-friendly house rentals available, with around 1,286 options throughout the area. Neighbourhoods like Old Town and New Town are particularly popular for families, offering spacious homes that cater to group needs. Properties in Old Town often feature large living areas, private pools, and are conveniently located near attractions such as the Ernest Hemingway Home and Museum and the bustling Duval Street, superb for family outings. Many of these homes come equipped with full kitchens and outdoor spaces, allowing for enjoyable meals and relaxation in the sun.Meanwhile, New Town presents larger residences with multiple bedrooms, expansive gardens, and amenities like game rooms and enclosed yards, making them ideal for families seeking entertainment options. This area is also close to Bayview Park, where families can enjoy playgrounds, sports courts, and picnic areas, adding to the outdoor fun.
Can I rent a holiday home with a pool or hot tub in Key West?
In Key West, there are plenty of holiday homes available for rent that come with pools and hot tubs, with around 1,610 options to choose from. This tropical paradise offers a range of neighbourhoods where these properties can be found, including the lively Old Town area, famous for its vibrant nightlife and historic charm, as well as the more tranquil surroundings of New Town, which provide a relaxed atmosphere.Travellers can expect a variety of amenities in these rentals, including private pools, luxurious hot tubs, outdoor patios or decks superb for sunbathing, and fully equipped kitchens ideal for preparing meals after a day of exploring. Find your rental in Key West with a pool or a hot tub.
Are there pet-friendly house rentals in Key West?
In Key West, there are numerous pet-friendly house rentals available, with over 700 options to choose from. Many of these properties are located in the vibrant Old Town area, providing easy access to the lively option and local attractions. Travellers can expect amenities such as private pools, outdoor spaces for pets, fully equipped kitchens, and spacious living areas, making them great for families or groups travelling with pets.The area is also known for its beautiful beaches, such as Smathers Beach and Fort Zachary Taylor State Park, both of which welcome pets on leashes, offering great opportunities for outdoor activities. Additionally, the nearby Key West Wildlife Centre is a pet-friendly point of interest, where visitors can learn about local wildlife and enjoy the surrounding nature. See all pet-friendly rentals in Key West.
Are there any remote work holiday rentals in Key West?
In Key West, there is an abundance of remote work holiday rentals available, with around 7,860 options to choose from. This vibrant destination offers a unique blend of tropical charm and modern amenities, making it an ideal spot for those looking to work remotely while enjoying a picturesque setting. Many properties come equipped with reliable high-speed internet and Wi-Fi, ensuring that you can stay connected during your stay.You can expect a variety of accommodations, from waterfront condos with stunning ocean views to charming cottages located in lush gardens. These rentals often feature comfortable workspaces, fully equipped kitchens for convenient meal preparation, and relaxing outdoor areas for taking breaks in the sun.In terms of location, consider staying near popular points of interest such as Mallory Square, where you can experience lively sunset celebrations, or the historic Old Town, which is rich in culture and offers delightful dining options. The nearby beaches and water sports activities provide great opportunities for unwinding after a day's work. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Key West?
In Key West, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals. Many properties also feature coffee and tea makers for a convenient morning brew. Outdoor spaces are a highlight, with numerous rentals offering decks or patios where visitors can relax and enjoy the tropical atmosphere, as well as balconies for taking in the views. Additionally, onsite parking is commonly available, making it easier for travellers with vehicles to explore the island.
When is the best time to visit Key West for a holiday rental?
The best time to visit Key West for a holiday rental is during the peak season from January to March, with March being particularly popular. This vibrant period attracts numerous visitors eager to soak up the sunshine, enjoy water sports, and explore the island's lively option. With temperatures typically ranging from 20 to 26 degrees Celsius, it's an ideal climate for outdoor activities such as snorkelling, diving, and leisurely beach days.During these months, the island comes alive with various festivals and events, allowing travellers to immerse themselves in the local culture while enjoying stunning sunsets and delicious seafood. The bustling streets are filled with fellow adventurers, creating a convivial ambience that enhances the overall experience.For those looking for a more budget-friendly option, consider visiting in October. While it falls within the low season, this month offers a unique opportunity to enjoy the tranquillity of Key West with fewer crowds. You can still partake in outdoor activities and explore the picturesque scenery without the hustle and bustle of peak season.
What are the top attractions in Key West?
In Key West, visitors can engage in a variety of attractions that showcase the island's unique charm and history. The historic Old Town is a must-see, where you can stroll along Duval Street, lined with lively bars, restaurants, and shops, and visit the iconic Ernest Hemingway Home and Museum. Nearby, the Southernmost Point Buoy offers a photo opportunity at the southernmost tip of the continental United States.For a taste of nature, the Key West Butterfly and Nature Conservatory presents a serene experience filled with exotic butterflies and lush gardens. Additionally, the vibrant Mallory Square is famous for its sunset celebrations, featuring street performers and local artisans, making it a superb spot to unwind at the end of the day.Water activities are abundant, with the crystal-clear waters providing opportunities for snorkelling and diving, particularly around the coral reefs.
Are all fees included in the Key West holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Key West holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Key West with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Key West holiday homes?
You can find great discounts on holiday homes in Key West on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Key West holiday home booking on Bookabach?
To find Key West holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Key West?
A long-stay holiday home in Key West is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Key West holiday home?
Book your Key West holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Key West?
Prices for holiday homes in Key West vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Key West to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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