Key West vacation rentals

We found 2,335 vacation rentals — enter your dates for availability

Select from 1103 houses, 270 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:Dec 12 - Dec 19

Image gallery for Atlantic Paradise by AvantStay | Great Location w/ & Shared Pool and hot tub!

Olympic sized swimming pool with ocean views.
9.6 out of 10 rating
Exceptional
(88 reviews)

Atlantic Paradise by AvantStay | Great Location w/ & Shared Pool and hot tub!

Key West, FL

6% off
Price is $552
$3,866 for 7 nights
All fees included
Atlantic Paradise by AvantStay | Great Location w/ & Shared Pool and hot tub!

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Find out more about Key West

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 when booking a vacation rental?
When booking a vacation rental in Key West, one of the best areas to consider is Old Town. This charming neighborhood is known for its historic architecture, vibrant nightlife, and close proximity to the beach. Staying in Old Town allows you to immerse yourself in the island's culture and enjoy attractions like the Ernest Hemingway Home and Museum and the lively Duval Street, where you'll find an array of shops, bars, and restaurants. With a wealth of vacation rental options available, from cozy cottages to luxurious homes, you'll have plenty of choices to suit your preferences.

Another fantastic area to explore is the Truman Annex, a gated community located just a short stroll from the heart of Old Town. This area is not only picturesque, with its lush landscaping and historic buildings, but it also offers easy access to some of Key West's top attractions like the Harry S. Truman Little White House and the beautiful beaches at Fort Zachary Taylor State Park. The Truman Annex features a range of vacation rentals, making it a sought-after spot for those looking to enjoy a more tranquil atmosphere while still being close to the action.

If you're interested in a more laid-back experience, consider the area around the Southernmost Point. Known for its iconic buoy marking the southernmost point in the continental United States, this neighborhood offers a relaxed vibe and stunning ocean views. It's ideal for leisurely strolls along the waterfront and is close to attractions like the Southernmost Beach and the Key West Butterfly and Nature Conservatory. The variety of rental properties in this area caters to different group sizes, ensuring that you can find the superb spot to unwind.

Each of these neighborhoods in Key West brings its own unique charm and attractions, making them excellent choices for your vacation rental stay.
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, Florida, travelers should consider the vibrant area around Smathers Beach, which is known for its picturesque sandy shores and clear turquoise waters. Many properties in this vicinity offer amenities such as private balconies, outdoor grills, and swimming pools, providing a great setting for relaxation and social gatherings after a day in the sun. This area is also conveniently located near local shops and restaurants, enhancing the overall experience.

Another great option is the Old Town neighborhood, where historic charm meets coastal living. Here, visitors can find quaint cottages and larger homes often featuring lush gardens, wrap-around porches, and easy access to nearby attractions such as the Southernmost Point and Duval Street. These rentals typically provide modern comforts like air conditioning, equipped kitchens, and Wi-Fi, ensuring a comfortable stay.

For those looking for a more tranquil setting, the area around Fort Zachary Taylor State Park offers a mix of beach access and natural beauty. Rentals nearby often come with amenities such as outdoor showers, picnic areas, and bike rentals, allowing guests to fully enjoy the park's scenic trails and beaches. Find your rental near the beach in Key West.
Are there any houseboat rentals in Key West?
In Key West, houseboat rentals are a unique and popular option, with about 55 available throughout the area. These houseboats are typically located in scenic waterfront neighborhoods, providing easy access to the vibrant local culture and attractions such as the Historic Seaport, Mallory Square, and the Ernest Hemingway Home and Museum. Travelers can expect a variety of amenities, including fully equipped kitchens, comfortable living spaces, and outdoor decks great for enjoying the picturesque views of the water and sunsets. Many houseboats also feature air conditioning, Wi-Fi, and some even come with additional recreational equipment like kayaks or paddleboards, making them an adventure-filled accommodation choice. 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 type of rental accommodation, with about 1,169 available throughout the island. Many of these houses are situated in charming neighborhoods, close to attractions like the Ernest Hemingway Home and Museum and the lively Duval Street. Travelers can expect spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor areas, often featuring pools or patios great for enjoying the tropical climate.

Condominiums are also a top option, with around 617 available. These often come with resort-style amenities such as pools, fitness centers, and easy beach access, making them ideal for those seeking a mix of convenience and leisure. Apartments and cottages provide additional choices for smaller groups or couples, with cozy interiors and access to local dining and shopping.
Are there any family house rentals in Key West?
In Key West, Florida, there are numerous family-friendly house rentals available—around 1,323 options scattered throughout the area. Neighborhoods like Old Town and New Town are particularly popular for families seeking spacious rooms. Properties in Old Town often provide roomy living spaces, private pools, and convenient access to local attractions such as the lively Duval Street and the historic Ernest Hemingway Home and Museum. Visitors will appreciate amenities like full kitchens, outdoor grilling areas, and beach gear, enhancing their vacation experience.

Meanwhile, New Town features larger homes with multiple bedrooms, expansive yards, and entertainment spaces, including game rooms and private patios. See all family-friendly rentals in Key West.
Can I rent a vacation home with a pool or hot tub in Key West?
In Key West, there are plenty of vacation homes available for rent that come with pools and hot tubs, with around 1,696 options to choose from. This tropical destination offers a range of neighborhoods where these properties can be found, including the bustling Old Town area, known for its historic charm and proximity to famous attractions, as well as the more tranquil residential areas like New Town, which provide a relaxed atmosphere.

Travelers can expect a variety of amenities in these rentals, such as private swimming pools, hot tubs, outdoor patios, and fully equipped kitchens, making them great for both relaxation and entertaining. 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 will find a wealth of pet-friendly house rentals, with around 795 options available throughout the area. Many of these rentals are located close to the vibrant Old Town, where visitors can enjoy easy access to local attractions and the scenic waterfront. Expect amenities such as spacious backyards for pets to roam, fully equipped kitchens for preparing meals, and comfortable living spaces that cater to families or groups.

The area is known for its picturesque beaches and parks, including the popular Fort Zachary Taylor Historic State Park, which is a great spot for pet owners to enjoy the outdoors with their furry companions. Additionally, many rental properties are within walking distance to pet-friendly restaurants and cafes, enhancing the overall experience for those traveling with pets. See all pet-friendly rentals in Key West.
Are there any remote work vacation rentals in Key West?
In Key West, there are numerous vacation rentals well-suited for remote work, with around 2,093 options available. Travelers can expect a variety of properties equipped with essential amenities for productivity, including dedicated desks, ergonomic chairs, high-speed Wi-Fi, and laptop workspaces. Many rentals also offer additional features like safe storage for valuables and business centers within resort properties, all designed to facilitate a seamless working environment.

The vibrant neighborhoods of Key West, such as Old Town and near the Historic Seaport, provide not only beautiful accommodations but also proximity to local attractions, restaurants, and shops. After work hours, guests can unwind at nearby beaches or explore the lively nightlife of the area. 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 vacation rental amenities include WiFi, kitchens, and patios, reflecting the area's laid-back tropical lifestyle. Many rentals also feature shared pools, allowing guests to cool off and socialize during their stay.
When is the best time to visit Key West for a vacation rental?
March is the most popular time to visit Key West, as it falls within the peak season from January to March. This vibrant month attracts sun-seekers and adventure travelers looking to indulge in the island's unique blend of culture, stunning beaches, and outdoor activities. The weather during this time is pleasantly warm, with temperatures typically ranging from the mid-60s to the low 80s Fahrenheit, creating ideal conditions for snorkeling, sailing, and exploring the iconic Duval Street.

In the heart of this peak season, visitors can enjoy lively festivals, such as Fantasy Fest, which adds a colorful twist to the already festive atmosphere. The array of water sports and excursions available during this time ensures that there's always something exciting to engage in, whether you're lounging on the beach or embarking on a sunset cruise.

For those seeking a more budget-friendly time to experience Key West, consider planning your trip in October. This month offers a quieter ambiance, allowing visitors to appreciate the local charm without the bustling crowds.
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?
In Key West, visitors can experience firsthand a variety of attractions that showcase the island's unique charm. The historic Old Town is a must-visit, featuring landmarks such as the Ernest Hemingway Home and Museum, where literary enthusiasts can learn about the famous author's life. Nearby, Mallory Square offers a vibrant atmosphere with its nightly sunset celebration, showcasing local performers and artisans.

For those interested in maritime history, the Key West Shipwreck Museum provides fascinating insights into the island's seafaring past. The Southernmost Point Buoy is another iconic spot, great for photo opportunities and a sense of geographical significance.

The lively Duvall Street is lined with bars, restaurants, and shops, making it a great area to find vacation rentals close to the action. Additionally, the beautiful beaches at Fort Zachary Taylor Historic State Park offer a great blend of history and relaxation, with opportunities for swimming and picnicking.

Exploring the nearby Dry Tortugas National Park is also a popular excursion, where visitors can enjoy snorkeling and the stunning views of Fort Jefferson.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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