Key West vacation rentals

We found 2,287 vacation rentals — enter your dates for availability

Welcome to Key West, where sun-drenched beaches meet vibrant coral reefs, inviting you to dive into an unforgettable tropical escape. Explore the charming streets of Old Town, indulge in local cuisine along bustling Duval Street, and immerse yourself in the island’s rich history. With diverse accommodations ranging from luxurious homes to cozy cottages, your group can enjoy the perfect blend of comfort and convenience, making your stay feel like a home away from home.

Holiday rentals with weekly discounts - Key West

Showing deals for:Dec 11 - Dec 18

Welcome to Octopus Garden!
Light Up The Night With The Pool Areas Accent Lighting!
Beautiful Kitchen With Every Kitchen Accessory Needed
Breakfast Bar & Dining Area
Exceptional
(215 reviews)

Perfect Location, Private Heated Pool, Pristine Luxury Home!

Key West

9% off
$2,013
$14,091 for 7 nights
All fees included
Perfect Location, Private Heated Pool, Pristine Luxury Home!
Interior
Marina
Private kitchen
Beach
Exceptional
(13 reviews)

All Included!!Private 3bedSailboat IncludingAccommodations&AllExcursions up to 6

Key West

9% off
$1,242
$8,691 for 7 nights
All fees included
All Included!!Private 3bedSailboat IncludingAccommodations&AllExcursions up to 6
Dining
Interior
Private kitchen
Interior
Wonderful
(199 reviews)

Sept Special@119.lodging + With 4 night stay 4th night FREE lodging!

Key West

8% off
$426
$2,980 for 7 nights
All fees included
Sept Special@119.lodging + With 4 night stay 4th night FREE lodging!
Living area
Marina
Pool
Master bedroom with king size bed
Exceptional
(7 reviews)

Luxury 2BR Condo • Oceans Edge Resort, Key West

Key West

8% off
$929
$6,504 for 7 nights
All fees included
Luxury 2BR Condo • Oceans Edge Resort, Key West
Living area
Pool
Dining
Private kitchen
Exceptional
(117 reviews)

Decorators own Coastal Chic home

Key West

8% off
$554
$3,879 for 7 nights
All fees included
Decorators own Coastal Chic home
Interior
Marina
Marina
Marina
Exceptional
(62 reviews)

Living the Dream Key West Style

Key West

9% off
$427
$2,989 for 7 nights
All fees included
Living the Dream Key West Style
Living area
Pool
The best deep water marina in Key West, with dry slips & wet slips available.
Property grounds
Exceptional
(154 reviews)

'Oceanside Oasis' Direct Ocean Views & 3 BR'S

Key West

8% off
$486
$3,399 for 7 nights
All fees included
'Oceanside Oasis' Direct Ocean Views & 3 BR'S
TV with games and books underneath
Large heated pool just steps from back porch
Second upstairs king bedroom with adjoining bath
Private kitchen
Exceptional
(215 reviews)

Casa Cove Beautiful Tropical 3 KING SUITES Sleeps 8- 2 miles to beach

Key West

8% off
$620
$4,340 for 7 nights
All fees included
Casa Cove Beautiful Tropical 3 KING SUITES Sleeps 8- 2 miles to beach
Dining
Golf
Pool
Living area
Exceptional
(45 reviews)

Key West - Stock Island

Key West

12% off
$399
$2,794 for 7 nights
All fees included
Key West - Stock Island

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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.

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 are the best areas to stay in a vacation rental in Key West?
Key West offers a variety of neighborhoods, each with its own charm, and Vrbo helps you find the perfect whole home for your trip, providing more space and privacy. The best area for your vacation rental in Key West depends on your travel style and what you want to experience. Here are some top picks:
  • Old Town Key West: This area has over 1,100 vacation rentals, including many houses, condos, and apartments. It's ideal for first-time visitors, couples, and groups, placing you within a 5-minute walk of attractions like Duval Street and the Southernmost Point.
  • Key West Historic District: With over 320 vacation rentals, primarily houses, apartments, and condos, this district is excellent for those who appreciate history and a vibrant atmosphere. You'll be within a 1-minute drive of Duval Street and a 2-minute drive of the Southernmost Point.
  • New Town: Offering over 170 vacation rentals, including houses and condos, New Town provides a quieter setting. It's a great choice for families, located about a 2-minute drive from Smathers Beach.
  • Beachside: This neighborhood features over 130 vacation rentals, mostly condos, and is perfect for beach lovers seeking ocean views and easy access to the water. It's just a 1-minute drive from Smathers Beach.
What are the most popular vacation rentals in Key West?
Houses and condos are the most popular types of vacation rentals in Key West, offering guests the space and privacy they seek. You'll find over 950 houses and nearly 600 condos available across the island. These property types are especially prevalent in Old Town Key West, which features over 1,100 vacation rentals, making it a bustling hub for visitors. Many guests choose these options for the comfort of a full kitchen, multiple bedrooms, and private outdoor areas, allowing groups and families to settle in comfortably.
What amenities do vacation rentals in Key West usually offer?
Vacation rentals in Key West typically offer a wide range of amenities designed for a comfortable and convenient stay. You'll often find fully equipped kitchens, high-speed internet, and free parking, which are essential for many guests. Many properties also feature swimming pools, hot tubs, and balconies or patios, perfect for enjoying the tropical climate. For those who enjoy outdoor living, properties with a yard or ocean views are also available.
Are there family-friendly vacation rentals in Key West?
Yes, Key West offers over 1,100 family-friendly vacation rentals, with houses and condos being common choices for families. Old Town Key West and New Town are popular areas for families, providing a mix of activities and quieter residential settings. Many of these vacation rentals come equipped with amenities that make family trips easier, such as full kitchens for meal preparation, laundry facilities, and heated pools for year-round enjoyment. You can also find properties that include travel cribs and highchairs, ensuring comfort for even the youngest guests.
Are there pet-friendly vacation rentals in Key West?
Yes, you'll find over 790 pet-friendly vacation rentals in Key West, making it easy to bring your furry companions along. Houses are a popular choice for pet owners, alongside a selection of condos and cottages. Old Town Key West and the Key West Historic District offer many options for guests with pets. These rentals often feature amenities like secured yards, providing a safe outdoor space for pets, and easy-clean floors for convenience.
What are the best areas for group vacation rentals in Key West?
Key West has over 780 vacation rentals suitable for large groups, providing ample space for everyone to enjoy their trip together. Old Town Key West and the Key West Historic District are excellent choices for groups, offering a high concentration of houses and villas. These properties often feature multiple bedrooms and bathrooms, large dining areas for shared meals, and convenient parking for several vehicles, ensuring a comfortable stay for everyone.
What are the best luxury vacation rentals in Key West?
Key West features over 1,200 luxury vacation rentals, providing upscale options for guests. Old Town Key West and the Beachside neighborhood are prime locations for these premium properties, with many houses, villas, and high-end condos available. These luxury rentals often boast amenities such as private pools, hot tubs, stunning ocean views, and spacious balconies, perfect for an indulgent escape.
Are there any budget-friendly vacation rentals in Key West?
Yes, Key West offers over 760 budget-friendly vacation rentals, providing great value for your trip. You'll find many options in Old Town Key West, the Key West Historic District, and Northside Resort, which tend to have a good selection of condos, cottages, and houseboats. These rentals often include amenities like full kitchens, which can help save on dining costs, and laundry facilities, adding to the overall value of your stay. Choosing a property with free parking can also contribute to a more economical trip.
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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