Key West vacation rentals

We found 2,319 vacation rentals — enter your dates for availability

Select from 1346 houses, 272 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

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Marina
10 out of 10 rating
Exceptional
(21 reviews)

Living the Dream Key West Style

Key West, FL

9% off
Price is $300
$2,102 for 7 nights
All fees included
Living the Dream Key West Style

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Find out more about Key West

Find out more about Key West

Why visit Key West

  1. Beautiful Beaches: Enjoy the stunning sandy shores and crystal-clear waters perfect for sunbathing and swimming.
  2. Cultural Exploration: Discover the vibrant Old Town filled with historic homes, charming streets, and local art.
  3. Outdoor Adventures: Engage in exciting activities like snorkeling, sailing, and exploring state parks.
  4. Relaxing Atmosphere: Experience the laid-back island vibe ideal for family vacations and romantic getaways.
  5. Diverse Accommodations: Choose from a variety of vacation rentals, including cozy cottages and beachfront condos.

Popular types of accommodation in Key West

If you're planning a getaway to Key West, you'll find a variety of excellent vacation rentals to suit your needs. The most popular options include houses, condos, and charming cottages. Each type of accommodation offers unique features and amenities, ensuring you have the perfect retreat. Explore our selection of Key West rentals and discover the ideal vacation home for your unforgettable trip to this tropical paradise.

  • Houses: The top choice for visitors to Key West, offering spacious accommodations for families or groups seeking comfort and privacy.
  • Condos: A popular option that combines convenience and amenities, perfect for those wanting a modern stay close to attractions.
  • Cottages: Quaint and charming, these rentals provide a cozy atmosphere ideal for couples or solo travelers.
  • Apartments: A versatile choice for vacationers, offering home-like settings for an extended stay.
  • Villas: Luxurious and spacious, these properties are perfect for those seeking a more upscale experience in paradise.**

Top attractions in Key West

Key West is a fantastic destination for families, business travelers, and city explorers alike. Visitors can enjoy stunning beaches, explore national and state parks, and tour historic houses. The area's attractions cater to those seeking cultural experiences, outdoor adventures, and relaxation by the sea. Whether you're looking to soak up the sun or dive into local history, Key West has something for everyone to enjoy.

  1. Duval Street: Experience the vibrant heart of Key West with lively shops, restaurants, and bars. This bustling street is renowned for its nightlife and eclectic atmosphere, perfect for strolling and soaking in the local culture.
  2. Mallory Square: Famous for its stunning sunset celebrations, Mallory Square offers a lively gathering place with street performers, artisan vendors, and breathtaking views of the Gulf. It's an ideal spot to unwind and enjoy the scenic beauty.
  3. Smathers Beach: Relax on this picturesque beach with soft sandy shores and crystal-clear waters. Smathers Beach is perfect for sunbathing, swimming, and water sports, providing a quintessential beach vibe in Key West.

Things to do recommended for families

Families will have a blast at the MLK Community Pool & Community Center in Key West, where they can enjoy swimming and outdoor fun together. The vibrant atmosphere makes it a perfect spot for kids to play while parents relax and soak up the sun.

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

If you're traveling with a group, as a family, bringing along pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Key West with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Key West with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with making sure there are suitable amenities, 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 vacation isn't truly fulfilling without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Key West: If you're searching for vacation rentals that offer discounts for extended 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 consider adding features like a parking space, a well-equipped kitchen, or a private pool to enhance your search.

Where to stay in Key West

Key West is a tropical paradise perfect for family vacations and romantic getaways. Explore the vibrant Old Town, where charming streets are filled with history and culture. Enjoy exciting excursions that showcase the island's natural beauty, from snorkeling to sunset sailing. With its relaxed atmosphere and diverse activities, Key West promises an unforgettable experience for every traveler looking to soak up the sun and enjoy island life.

  • Old Town Key West: Old Town Key West is a vibrant neighborhood known for its historic charm and lively atmosphere. Nestled in the heart of Key West, this area offers a unique blend of shopping, dining, and entertainment. Visitors can stroll along charming streets lined with colorful homes and famous landmarks, including the iconic Southernmost Point Buoy. Enjoy the local beaches, perfect for families, or explore boutique shops and galleries that showcase the island's art scene. Old Town is an ideal base for those looking to immerse themselves in the island's rich culture and history while enjoying a laid-back vacation experience.
  • Key West Historic District: The Key West Historic District is a captivating neighborhood that transports visitors back in time with its preserved architecture and rich history. Located close to the waterfront, this district is home to many of Key West's most significant historical sites, including the Ernest Hemingway Home and Museum. As you wander through its picturesque streets, you'll find delightful cafes, shops, and lush gardens. The nearby beaches provide a perfect spot for relaxation, while the area's vibrant nightlife offers plenty of entertainment options. The Historic District is ideal for travelers seeking an authentic taste of Key West's past while enjoying modern comforts.
  • New Town: New Town offers a more contemporary vibe in contrast to the historic charm of Old Town. This neighborhood is perfect for families and business travelers alike, featuring a variety of shopping centers, restaurants, and recreational facilities. New Town is home to spacious parks and beautiful beaches, ideal for sunbathing and water sports. Visitors can easily access local attractions and enjoy a range of activities, from outdoor adventures to dining experiences. With its modern amenities and family-friendly atmosphere, New Town is a great place to unwind while still being close to the action of Key West.

Booking with Vrbo is a breeze

Looking to save money on your next trip? Consider being flexible with your travel dates, as this can lead to significant price differences. Also, extending your stay can often result in even greater savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash™ on your booking. Being the planner definitely has its perks! When you join our travel rewards program, One Key, you'll gain immediate access to member savings and have the opportunity to earn and redeem OneKeyCash™ on qualifying reservations. Sign up today and begin enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your travels. You can start new trips, pick up right where you left off, or easily view and organize your itineraries. All the properties you've saved or booked are now neatly categorized under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-ca/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.