Key West holiday lettings

We found 2,302 holiday rentals — enter your dates for availability
Select from 1001 houses, 290 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.

Find spaces that suit your style

Why visit Key West

  • Stunning Beaches: Key West offers idyllic beaches perfect for sunbathing, swimming, and water sports, providing a relaxing seaside experience.
  • Historic Landmarks: Explore the rich history of Key West through its charming historic houses and museums, including the renowned Ernest Hemingway Home and Museum.
  • Iconic Sunsets: Witness breathtaking sunsets at Mallory Square, a renowned spot for evening celebrations and local performances.
  • Cultural Vibrancy: Experience a lively atmosphere filled with art galleries, local cuisine, and vibrant festivals that showcase the island's unique culture.
  • Outdoor Adventures: Engage in diverse outdoor activities, from snorkelling and diving to exploring nearby national parks, making it perfect for nature enthusiasts.

Popular types of accommodation in Key West

Embark on a delightful getaway to Key West, Florida, a charming city brimming with vibrant culture and stunning natural beauty. From the iconic sunsets at Mallory Square to the historic Ernest Hemingway Home and Museum, there's no shortage of attractions to explore. Choose from a variety of accommodations, including houses, condos, and cosy cottages, ensuring a perfect base to enjoy captivating beaches and unforgettable experiences in this tropical paradise.

  • Houses: The top choice for visitors to Key West, these homes offer spacious and comfortable living, ideal for families or groups seeking privacy.
  • Condos: A popular option for those wanting modern amenities and a community feel, condos provide easy access to local attractions and beaches.
  • Cottages: Quaint and charming, cottages are perfect for a romantic getaway or a peaceful retreat, often with a unique character.
  • Apartments: Offering convenience in the heart of the city, apartments are a great choice for couples or solo travellers looking for a central base.
  • Villas: Luxurious and spacious, villas are ideal for those seeking an upscale experience with ample amenities and privacy.**

Top attractions in Key West

Key West, Florida, is a vibrant destination perfect for family, cultural, and outdoor experiences. Visitors can explore stunning beaches, enjoy the natural beauty of nearby national parks, and discover the charm of historic houses. Whether you’re seeking relaxation by the sea or immersive cultural insights, Key West offers a diverse range of attractions that cater to all interests, making it an ideal vacation spot for everyone.

  • Duval Street: A vibrant thoroughfare, Duval Street is the heartbeat of Key West, lined with eclectic shops, lively bars, and charming eateries. The atmosphere buzzes with energy, making it a perfect spot for people-watching and soaking in the local culture.
  • Mallory Square: Renowned for its stunning sunset celebrations, Mallory Square offers a lively gathering space where street performers and local artists showcase their talents against a backdrop of breathtaking ocean views.
  • Smathers Beach: A picturesque stretch of sand, Smathers Beach is ideal for sunbathing and water sports, providing a relaxing beach vibe amidst swaying palm trees and crystal-clear waters.

Things to do recommended for couples

For a romantic getaway in Key West, indulge in a sunset sail on a catamaran, explore the lush gardens of the Ernest Hemingway Home, or enjoy a candlelit dinner at a waterfront restaurant. Strolling along Mallory Square is perfect for watching the sunset together.

Things to do recommended for families

Families visiting Key West can explore the vibrant marine life at the Key West Aquarium, enjoy a thrilling day at the beach, and take a scenic bike ride along the picturesque shorelines. Don't miss the chance to discover the fascinating history at the Ernest Hemingway Home and Museum.

Things to do recommended for groups

Groups visiting Key West can embark on a thrilling sunset sail, explore the vibrant local art scene at galleries, and indulge in fresh seafood at lively waterfront restaurants. Don’t miss the chance to experience the famous Duval Street's nightlife and the historic Ernest Hemingway Home.

*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

If you're travelling with a group, your family, bringing along pets, or seeking longer stays, it's important to filter according to your key priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Key West with a group: Think about how many bedrooms you require, along with conveniences like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can refine your search for all of these features, and more, on Vrbo.
  • Traveling to Key West with young kids: Travelling with young children can present its challenges. It’s essential to prioritise their comfort and safety, along with finding age-appropriate facilities, 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 wouldn't feel complete without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Key West: If you're seeking holiday rentals with discounts 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 monthly rentals. Don’t forget to include features such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Key West

Key West, Florida, is a charming island city perfect for family getaways, romantic escapes, and business trips alike. Visitors can immerse themselves in its vibrant atmosphere by exploring historic landmarks, enjoying tropical excursions, and relaxing on sun-kissed beaches. The unique blend of culture, natural beauty, and lively entertainment makes Key West an unforgettable destination for any traveller seeking a delightful experience in this picturesque corner of the United States.

  • Old Town Key West: Nestled in the heart of Key West, Old Town is a vibrant neighbourhood brimming with history and charm. This area is renowned for its unique blend of city-themed, family-friendly, and business-oriented experiences. Visitors can enjoy a leisurely stroll along its picturesque streets, exploring a variety of shops and boutiques. The nearby beaches provide opportunities for relaxation and family fun, making it a perfect destination for all ages. Iconic landmarks, such as the Ernest Hemingway Home and Museum, further enrich the cultural experience.
  • Stock Island: Located adjacent to Key West, Stock Island is a tranquil island retreat that offers a more laid-back atmosphere. It is an ideal destination for families and city explorers seeking a business-themed getaway. Visitors can indulge in shopping at local markets and enjoy a round of golf at the nearby course. With its pristine beaches and inviting streets, Stock Island provides a serene escape while remaining close to the lively atmosphere of Key West. The island's relaxed vibe and natural beauty make it a delightful addition to your itinerary.
  • Key West Historic District: The Key West Historic District showcases the rich cultural heritage of the area, characterised by its charming architecture and vibrant streets. This neighbourhood offers visitors an engaging city-themed experience, perfect for families and business travellers alike. You can explore its eclectic mix of shops and resorts, all while soaking in the area’s storied past. The close proximity to beautiful beaches and community spaces makes it a wonderful spot to unwind and enjoy the local atmosphere, ensuring a memorable visit.

Booking with Vrbo is simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate significantly. Moreover, extending your stay often results in substantial savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for planning new getaways, managing your existing arrangements, and reviewing your bookings. Your saved or reserved properties are conveniently organised into categories: Potential, Upcoming, or Current Trips. To discover more about 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. Take in top local attractions such as Duval Street and Mallory Square. 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:

  • Southernmost Point (0.6 mi / 1 km)
  • Florida Keys Beaches (16 mi / 25.8 km)
  • Audubon House and Tropical Gardens (0.3 mi / 0.6 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)

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.
How much does it cost to rent a holiday home in Key West?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Key West to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Key West holiday house rentals?
You can find great discounts on house rentals in Key West on Vrbo, 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.
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.
Can I find long-stay holiday rentals in Key West?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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 Vrbo.
Are there any Key West holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
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.
How early should I book a Key West holiday rental?
Book your Key West holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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.
Can I change or cancel my Key West home rental booking on Vrbo?
To find Key West holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Key West holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

More holiday ideas