Key West vacation rentals

We found 2,354 vacation rentals — enter your dates for availability

Select from 1041 houses, 285 apartments, and other vacation rentals to find the perfect place for your stay in Key West. Whether you’re staying in a vacation home with family, friends, or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, such as parking and air conditioning. Whatever you're looking for, you'll find a rental for everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Key West

Showing deals for:May 22 - May 29

Image gallery for Living the Dream Key West Style

Marina
10 out of 10, Exceptional, (44 reviews)
Exceptional
(44 reviews)

Living the Dream Key West Style

Key West

9% off
Price is $426
$2,985 for 7 nights
All fees included
Living the Dream Key West Style

Find spaces that suit your style

Find out more about Key West

Why visit Key West

  • Beautiful Beaches: Key West boasts stunning beaches perfect for relaxation and water sports.
  • Rich History: Explore historic homes and landmarks that showcase the island's unique past.
  • Outdoor Activities: Engage in snorkeling, diving, and fishing in the vibrant waters surrounding the island.
  • Vibrant Culture: Experience lively festivals, art galleries, and local music that reflect the island's cultural diversity.
  • Relaxing Accommodations: Choose from luxury resorts, cozy cottages, or stylish condos for a comfortable stay.

Popular types of accommodation in Key West

Planning your getaway to Key West? The next exciting step is selecting the perfect place to stay. Discover the top choices for Key West vacation rentals, including houses, cozy cottages, and modern condos. Whether you're looking for spacious house rentals or stylish key west condos, we've got you covered. Enjoy the sun, sea, and savings as you find your ideal accommodation for an unforgettable experience.

  • Houses: The top choice for visitors to Key West, offering spacious accommodations ideal for families and groups, ensuring a home-like atmosphere.
  • Condos: A popular option for those seeking modern amenities and a shared community vibe, perfect for couples or small families.
  • Cottages: These quaint and charming homes provide a cozy retreat, ideal for a romantic getaway or a peaceful escape.
  • Apartments: A convenient choice for travelers looking for flexibility and access to local life, often situated in vibrant neighborhoods.
  • Villas: Luxurious spaces that offer privacy and stunning views, perfect for those wanting an upscale experience in paradise.**

Top attractions in Key West

Key West is a fantastic destination for families, business travelers, and those seeking a vibrant city experience. Visitors can explore beautiful beaches, national parks, and historic houses, all while enjoying the rich culture and outdoor activities the area has to offer. Whether you're looking for relaxation or adventure, Key West has something for everyone to make your vacation unforgettable.

  • Duval Street: A lively street filled with vibrant shops, restaurants, and bars, Duval Street captures the essence of Key West's energetic city vibe, making it perfect for strolling, dining, and nightlife.
  • Southernmost Point: This iconic landmark marks the southernmost tip of the continental United States. It offers a unique cultural experience, with photo opportunities at its famous buoy and a glimpse into Key West's rich history.
  • Mallory Square: Known for its stunning sunset celebrations, Mallory Square is a bustling modern square that showcases local artisans, street performers, and breathtaking views of the Gulf of Mexico.

Things to do recommended for couples

Planning a romantic getaway in Key West? Enjoy a sunset sail on a catamaran, explore the charming streets lined with vibrant houses, or indulge in a candlelit dinner at a waterfront restaurant. Don't forget to visit the famous Southernmost Point for a perfect photo opportunity together.

Things to do recommended for families

Families visiting Key West can cool off at the MLK Community Pool & Community Center, where kids can splash around and enjoy sports in a vibrant outdoor setting perfect for family bonding and fun activities.

Things to do recommended for groups

In Key West, your group can enjoy a round of golf at the Key West Golf Club, experience captivating performances at the Waterfront Playhouse, and browse unique items at The Kite House. These activities promise a blend of outdoor fun, culture, and shopping for everyone.

*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 traveling with a group, family, pets, or planning an extended stay, be sure to use the appropriate filters to meet your specific needs. Here are some helpful tips for booking on Vrbo.

  • Traveling to Key West with a group: Think about how many bedrooms you require, as well as additional features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Key West with young kids: Traveling with young kids can be tricky. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, keeping in mind the distance to family-friendly attractions is a wise choice.
  • Taking your pets with you to Key West: For many families, a vacation wouldn’t feel complete without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Key West: If you’re in search of vacation rentals that offer discounts for stays of a month or more, you’ve come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Key West

Key West, Florida, offers a vibrant blend of family-friendly activities, romantic escapes, and exciting excursions. Explore its historic homes, relax at luxury resorts, and enjoy the island's tropical atmosphere. With excellent recreational facilities and an inviting ambiance, this unique city is perfect for any vacation type—be it a leisurely family getaway or a business trip. Don't miss the chance to experience the charm and beauty of Key West and its neighboring regions.

  • Old Town Key West: Old Town Key West is a vibrant neighborhood that epitomizes the charm of this tropical paradise. Located around the heart of Key West, it offers a delightful mix of city-themed experiences perfect for families and business travelers alike. Wander through the historic streets lined with colorful architecture, explore unique shops, and indulge in local cuisine at waterfront restaurants. The area is home to beautiful beaches, making it an ideal spot for sunbathing and family outings. Don't miss the iconic sunset celebrations at Mallory Square, where you can soak in the lively atmosphere and stunning views.
  • Stock Island: Stock Island is a hidden gem just a short distance from Key West, known for its laid-back vibe and outdoor adventures. This island offers a family-friendly environment with various activities that cater to both the adventurous and those looking to relax. Explore the local shops, enjoy a round of golf, or take in the scenic marina views. The nearby beaches provide perfect spots for swimming and sunbathing, while the lush landscapes invite you to partake in outdoor activities like biking and fishing. Stock Island is an excellent choice for travelers seeking a more tranquil escape just minutes from the bustling atmosphere of Key West.
  • Key West Historic District: The Key West Historic District is a captivating neighborhood that showcases the rich history and culture of the island. Located in close proximity to downtown Key West, this area is perfect for those interested in exploring the city’s heritage. Visitors can enjoy shopping at quaint boutiques, dining at renowned restaurants, and staying at charming resorts. The district features picturesque streets and family-friendly beaches, providing a perfect blend of relaxation and exploration. Be sure to visit the Ernest Hemingway Home and Museum and other historic sites that offer insights into the island's storied past.

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming trip? Keeping your travel dates flexible can help, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo rental that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner really pays off. When you join our travel rewards program, One Key, you'll gain immediate access to member discounts and the ability to earn and redeem OneKeyCash on eligible reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides a convenient platform for planning your trips, allowing you to start new itineraries, continue existing ones, or manage your reservations. Your saved and booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Explore scenic beauty from a Key West villa rental

The unique island city of Key West is one of the best vacation spots for Florida villa rentals. You can experience mile after mile of emerald waters and coral reefs as you drive the Overseas Highway along the Florida Keys archipelago to the farthest southern point that is Key West. You've never had a vacation getaway quite like Key West. This historic former pirate haven is one of the best spots for snorkeling and diving anywhere in Florida. If you love shrimp or crabs, you are in for a delicious treat thanks to the fresh seafood restaurants in Key West.

 

Admire local talent at Studios of Key West

Free-spirited Key West has long been a haven for artists and creatives. There's no better place to discover the scene than The Studios of Key West, a 3-story space showcasing works from local artists. Continue the theme at Hemingway House, a handsome Spanish Colonial estate that was once a sanctuary for the American novelist. If you want to meet one of Key West's most passionate eco-activists, head to Nancy Forrester's Secret Garden. From chirpy parrots to multicolored macaws, this backyard oasis offers a unique opportunity to get up close and personal with exotic Floridian birds.

Splash-happy in Key West

As the sun starts to set, Mallory Square gears up for a night of family-friendly fun. It's essentially one big street party, with fire breathers, tightrope walking dogs, tumbling acrobats and more. You'll also find plenty of action on Duval Street, a lively strip lined with neon-lit bars, theaters, galleries and boutiques. For a quieter scene, why not retreat to the deck of your Key West vacation rental villa for fruity Rum Runner cocktails and Floridian sunsets? For more action, you can snorkel at coral reefs, kayak in crystal-clear water, swim with dolphins, sail on catamarans and more.

Catch Key West's Fantasy Fest celebrations

Craving a dose of winter sunshine? Escape to Key West vacation rentals and you'll find yourself immersed in a tightknit community of locals. Chances are you'll soon be sharing key lime pie with your new neighbors. Locals cite spring as a Key West sweet spot. Crowds taper off and temperatures continue to hover around the 80s. Visit in the last week of October and you'll catch Key West's raucous Fantasy Fest celebrations. The 10-day street party sees the island come alive with pet parades, burlesque shows, costumed events, street food stalls and more.

Pet-friendly vacations in Key West

With a footprint measuring in at just 7 square miles, Key West feels wonderfully intimate. It's part of the Florida Keys archipelago and sits just 90 miles from Cuba. You can find out more about the low-lying archipelago at the Florida Keys Eco-Discovery Center, a family-friendly learning space filled with interactive displays and rainbow-colored sea creatures. traveling with Fido? No problem. Floridians love their furry friends, which means you'll find plenty of pet-friendly Key West vacation rentals.

Transportation to and around Key West

Fly into Key West Intl. Airport (EYW), the closest airport, located 3 mi (4.8 km) from the city center.

Frequently asked questions

What is the best area to stay in Key West, Florida, United States of America when booking a vacation rental?
When considering the best area to stay in Key West, Florida, the Old Town neighborhood stands out as a premier choice for vacation rentals. This vibrant area is known for its historic charm, featuring colorful architecture and a lively option. One of the major attractions is the famous Duval Street, where visitors can explore a variety of shops, restaurants, and bars, all while soaking in the island's unique culture. Additionally, the Ernest Hemingway Home and Museum provides a fascinating glimpse into the life of the iconic author, making it a must-visit for literature enthusiasts.

Another fantastic option is the area near the Southernmost Point Buoy, a popular landmark that draws many tourists eager to capture the great photo. Staying here allows easy access to stunning beaches and waterfront activities, such as snorkeling and sunset cruises. In terms of vacation rentals, both Old Town and the Southernmost Point area offer a diverse range of properties, providing plenty of choices that cater to different preferences and budgets.
How much does it cost to rent a vacation home in Key West?
Prices for vacation 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 vacation 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, travelers should focus on the areas around Smathers Beach and the Historic District. Smathers Beach offers a vibrant setting with beautiful sandy shores, making it a prime location for vacation rentals. Many properties in this area come equipped with amenities like private balconies, outdoor lounging spaces, and full kitchens, great for enjoying the coastal lifestyle. Some rentals also provide direct beach access, allowing guests to easily enjoy the sun and surf.

In the Historic District, visitors can find charming conch-style homes and cottages that reflect the island's unique architecture. These properties often feature lush gardens, pools, and easy access to local attractions such as the Ernest Hemingway Home and Museum and Mallory Square, known for its stunning sunsets. Many homes in this area are designed for comfort and convenience, offering amenities like air conditioning, Wi-Fi, and outdoor grilling areas for entertaining.

Additionally, the area around Fort Zachary Taylor State Park is another excellent option for beach house rentals. This location combines historical significance with beautiful beach access, and nearby properties often include outdoor showers, picnic areas, and proximity to nature trails for hiking and exploration. Find your rental near the beach in Key West.
Are there any houseboat rentals in Key West?
In Key West, there are about 55 houseboat vacation rentals available, making them a unique accommodation option in this vibrant destination. These houseboats are typically located in scenic marinas or waterfront areas, allowing guests to enjoy stunning views of the water and easy access to local attractions. Travelers can expect amenities such as fully equipped kitchens, cozy living spaces, and outdoor decks for sunbathing or dining al fresco. Many houseboats also come with air conditioning, Wi-Fi, and some even feature kayaks or paddleboards for exploring the surrounding waters. See all houseboats in Key West.
What is the most popular type of vacation rental accomodation in Key West?
In Key West, vacation houses are the most popular rental option, with nearly 988 available throughout the area. These houses often feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families and larger groups. Many also include outdoor spaces such as private patios or decks, great for enjoying the warm Florida weather.

Condos are another common choice, with around 604 options found close to popular attractions like Duval Street and the Southernmost Point Buoy. These typically come with amenities such as pools, fitness centers, and easy access to the beach.

Apartments, numbering around 236, offer a more compact yet comfortable stay, often featuring cozy living areas and kitchens, while cottages and houseboats provide unique and charming alternatives for travelers looking for something different.
Are there any family house rentals in Key West?
In Key West, Florida, there is a wealth of family-friendly house rentals available, with around 1,286 options to choose from. Neighborhoods like Old Town and New Town are particularly popular for families, offering spacious homes close to many attractions. In Old Town, visitors can find properties featuring large living areas, private pools, and easy access to highlights such as the Ernest Hemingway Home and Museum and the vibrant Duval Street. These homes often come equipped with full kitchens and outdoor grilling areas, great for family gatherings after a day of exploration.

Meanwhile, New Town caters to larger groups, showcasing homes with multiple bedrooms and ample outdoor space, including game rooms and enclosed yards. This area is conveniently located near Bayview Park, where families can enjoy playgrounds and sports facilities.
Can I rent a vacation home with a pool or hot tub in Key West?
In Key West, travelers can find a wide selection of vacation homes available for rent that feature pools and hot tubs, with around 1,610 options to choose from. The island's vibrant neighborhoods, including the historic Old Town and the quieter areas like New Town, offer a variety of rental properties. Many of these homes come equipped with private pools, inviting hot tubs, and spacious outdoor areas great for enjoying the tropical climate.

Amenities often include fully equipped kitchens, allowing for convenient meal preparation, as well as comfortable living spaces ideal for relaxation after a day of exploring. Some properties may even feature outdoor kitchens or BBQ areas, enhancing the experience of dining al fresco. Find your rental in Key West with a pool or a hot tub.
Can I find long-stay vacation rentals in Key West?
A long-stay vacation rental in Key West is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Key West?
In Key West, travelers can find a wide selection of pet-friendly vacation house rentals, with over 700 options available. Many of these properties are designed to accommodate pets, ensuring a comfortable stay for both guests and their furry companions. Expect amenities such as fenced yards, outdoor patios, and spacious living areas, which provide a ideal setting for relaxation after a day of exploring the island.

Key West is known for its vibrant neighborhoods like Old Town, where rental homes often feature charming architecture and easy access to local attractions. Vacation rentals in this area are typically equipped with modern kitchens, Wi-Fi, and comfortable furnishings. Additionally, many homes are just a short walk or bike ride away from pet-friendly beaches and parks, making it easy to enjoy outdoor activities with your pet.

For those looking to explore, the nearby Dog Beach offers a great spot for pets to play in the sand and surf, while the surrounding gardens and waterfront areas provide scenic walking paths.
Are there any remote work vacation rentals in Key West?
In Key West, there are numerous options for remote work vacation rentals, with around 1,965 available throughout the area. This vibrant city offers a unique blend of relaxation and productivity, making it an ideal destination for those looking to work remotely. Properties typically provide essential amenities such as high-speed internet, Wi-Fi access, and dedicated workspaces, ensuring that you can stay connected while enjoying the tropical atmosphere.

Travelers can expect a range of accommodations, from charming cottages to modern condos, often featuring comfortable living areas, full kitchens for meal preparation, and outdoor spaces to unwind after a day of work. Many rentals are conveniently located near popular attractions like the Ernest Hemingway Home and Museum, the lively Duval Street, and beautiful beaches, providing ample opportunities for recreation during your downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Key West vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Key West with parking available—perfect for families or travelers 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 meals with ease. Many accommodations offer coffee and tea makers for a comforting start to the day. Decks or patios are also common, providing outdoor spaces to relax and enjoy the island's tropical climate. Onsite parking is available, which is a valuable perk in this bustling destination.
When is the best time to visit Key West for a vacation rental?
March is the best time to visit Key West for a vacation rental, as it falls within the peak season that runs from January to March. During this vibrant period, travelers flock to the island to enjoy the warm, sunny weather and the lively option that accompanies it. With average temperatures ranging from the mid-70s to low 80s Fahrenheit, outdoor activities such as snorkeling, diving, and exploring the famous Duval Street become all the more enjoyable.

The peak season brings a surge of tourists, but the ambiance remains inviting, making it an ideal time for those seeking both relaxation and adventure. Whether you're lounging on the beach, indulging in fresh seafood, or partaking in various water sports, the options are plentiful.

If you're looking for a more budget-friendly experience, consider visiting in October. This month offers a quieter atmosphere while still providing beautiful weather and a chance to witness the island's charm without the bustling crowds. It's a great time for leisurely strolls through the historic districts or enjoying local art galleries.

Ultimately, your ideal time to visit Key West will depend on whether you prefer the high-energy vibe of peak season or the more relaxed pace offered in the fall.
How early should I book a Key West vacation rental?
Book your Key West vacation 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 vacation 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, Florida, United States of America?
In Key West, visitors can explore a variety of attractions that highlight the island's unique charm. The Historic Old Town is a must-visit, where you can stroll down Duval Street, known for its lively option, dining options, and shops. The Ernest Hemingway Home and Museum offers a glimpse into the life of the famous author and features beautiful gardens.

Nearby, Mallory Square is famous for its sunset celebrations, where locals and tourists gather to watch the sun dip below the horizon, often accompanied by street performers and food vendors. For those interested in maritime history, the Key West Shipwreck Museum provides engaging exhibits and a lookout tower offering panoramic views of the area.

Nature enthusiasts can head to the Dry Tortugas National Park, accessible by boat or seaplane, which is known for its stunning coral reefs and historic Fort Jefferson. Additionally, the beaches of Fort Zachary Taylor State Park provide a more tranquil atmosphere for sunbathing and swimming.
Can I change or cancel my Key West home rental booking on Vrbo?
To find Key West vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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.

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