Key West vacation rentals

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

Select from 1116 houses, 287 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:Feb 20 - Feb 27

Image gallery for Catchlight House at Lunara Bay

Heated Private Pool
9.8 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)

Catchlight House at Lunara Bay

Key West, FL

10% off
Price is CA $3,587
CA $30,970 total
includes taxes & fees
Catchlight House at Lunara Bay

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Find out more about Key West

Why visit Key West

  • Stunning Beaches: Relax on beautiful sun-kissed beaches, perfect for swimming and water sports.
  • Historic Sites: Discover captivating historic houses and landmarks that showcase the island's rich heritage.
  • Vibrant Culture: Enjoy the lively local art scene and diverse cultural experiences throughout the island.
  • Outdoor Adventures: Engage in various outdoor activities, from snorkeling to exploring the national park.
  • Family-Friendly Atmosphere: Experience a welcoming environment suitable for families, couples, and solo travellers alike.

Popular types of accommodation in Key West

Explore the charm of Key West with our selection of vacation rentals, including houses, condos, and cozy cottages. Whether you're planning a family getaway or a romantic retreat, there's something for everyone. With transparent information and savings at your fingertips, you'll find the perfect Key West accommodation to suit your needs. Start your Key West vacation today and enjoy the beautiful surroundings and laid-back atmosphere.

  • Houses: The top choice for visitors to Key West, these homes offer a spacious and comfortable setting for families or groups looking to unwind.
  • Condos: A close second, condos provide modern amenities and often beautiful views, perfect for those wanting a bit of luxury.
  • Cottages: These quaint and charming rentals offer a cozy escape, ideal for couples seeking a romantic getaway.
  • Apartments: A practical option for solo travellers or smaller groups, apartments allow for easy access to local attractions.
  • Villas: Offering upscale living with style, villas are perfect for those wanting a lavish experience in paradise.**

Top attractions in Key West

Key West offers a delightful mix of family-friendly, city, and business-themed vacations. Visitors can explore beautiful beaches, the stunning national park, and captivating historic houses. With a vibrant culture and plenty of outdoor activities, Key West is perfect for those seeking relaxation or adventure. Whether you’re travelling solo or with loved ones, there's something for everyone to enjoy in this charming destination.

  • Duval Street: This lively street is the heart of Key West, bustling with shops, restaurants, and vibrant nightlife. Experience the local culture, enjoy street performances, and indulge in delicious cuisine.
  • Southernmost Point: A must-visit landmark, this iconic buoy marks the southernmost tip of the continental U.S. Capture a photo with this famous symbol and soak in the rich history and culture of the area.
  • Mallory Square: A vibrant gathering place, known for its stunning sunset celebrations. Enjoy street performers, local artisans, and a beautiful view of the Gulf of Mexico.

Things to do recommended for couples

Key West offers a romantic escape with sunset sails over the turquoise waters, intimate dinners at quaint seaside restaurants, and leisurely strolls along the historic streets. Don't miss a visit to the beautiful beaches for a relaxing day under the sun, perfect for couples seeking a memorable experience.

Things to do recommended for families

Families will love the MLK Community Pool & Community Center, a fantastic spot in Key West offering a refreshing pool experience. With sports and outdoor activities, it's perfect for creating lasting memories while enjoying a fun family day together.

Things to do recommended for groups

Enjoy a round of golf at the Key West Golf Club, soak in culture at the Red Barn Theater, or browse unique finds at The Kite House. These experiences offer a perfect blend of outdoor fun, entertainment, and local charm for your group getaway.

*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 planning a trip with friends, family, pets, or need accommodations for an extended period, it’s important to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Key West with a group: Think about how many bedrooms you require, as well as additional features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Key West with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, including access to suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Key West: For many, a family vacation wouldn’t feel complete without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties 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 searching for vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By utilizing the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding options like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay in Key West

Key West offers a unique blend of tropical charm and vibrant culture, making it an ideal destination for families, couples, and business travellers alike. Explore elegant vacation rentals, luxurious estates, and historic homes that reflect the island's rich heritage. With opportunities for excursions and a family-friendly atmosphere, Key West promises unforgettable experiences, whether you're lounging on sun-kissed beaches or discovering the local art scene. Dive into the laid-back vibe of this enchanting island paradise.

  • Old Town Key West: Old Town Key West is a vibrant neighborhood that captures the charm of island life. Nestled in the heart of Key West, this area is known for its lively streets filled with shops, restaurants, and art galleries. Visitors can enjoy a “city themed” experience while exploring historical sites such as the Ernest Hemingway Home and Museum. The proximity to beautiful beaches makes it an ideal spot for families looking to relax and enjoy the sun. You’ll find a variety of resorts and shopping areas that cater to both leisure and business travelers.
  • Stock Island: Just a stone's throw from Key West, Stock Island is a hidden gem that offers a more laid-back, outdoor experience. Known for its natural beauty, visitors can enjoy activities such as golfing, fishing, and exploring marinas. The island vibe is perfect for families and those seeking outdoor adventures. With a few shopping areas and local eateries, Stock Island provides a unique blend of relaxation and recreation, making it an excellent spot for those looking to escape the hustle and bustle.
  • Key West Historic District: The Key West Historic District is a captivating area that showcases the island's rich history and culture. This neighborhood features charming architecture and a variety of attractions, including local shops and resorts. Ideal for families and business travelers alike, the district offers easy access to beautiful family-friendly beaches. Strolling through the historic streets, visitors will discover landmarks that tell the story of this unique island, making it a must-visit for anyone looking to immerse themselves in the local culture.

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as this can lead to significant price differences. Furthermore, opting for a longer stay often results in excellent savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a user-friendly platform where you can effortlessly plan new trips, resume your previous arrangements, or manage your travel itineraries. You'll discover your saved or booked properties neatly organized into categories like Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Take in the picturesque beauty of Key West

The area's live music and festivals are just a few of the reasons to vacation in Key West. This city's bars, seaside and boating draw many visitors. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Key West

Are you hoping to find top things to see and do in the area? Travelers enjoy fun activities like boating and biking. Venture out of your vacation home and experience everything that Key West has to offer. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Key West Golf Club (4 mi / 6.5 km)
  • The Kite House (0.3 mi / 0.5 km)
  • MLK Community Pool & Community Center (0.5 mi / 0.8 km)
  • Blue Hole (28.6 mi / 46.1 km)

Exploring the natural landscape of Key West

Travelers love Key West for its breathtaking sunsets and beautiful ocean views. Whether you're looking for exciting outdoor activities or just want to take in the scenery, Key West is a great place to get out in nature. Here are some of the area’s most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • Audubon House and Tropical Gardens (0.3 mi / 0.6 km)
  • Key West Butterfly and Nature Conservatory (0.6 mi / 1 km)
  • Southernmost Point (0.6 mi / 1 km)
  • South Beach (0.7 mi / 1.1 km)
  • Simonton Beach (0.8 mi / 1.2 km)
  • Truman Beach (0.9 mi / 1.4 km)

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, the Old Town neighbourhood is often regarded as the best area to stay. This charming part of the island captures the essence of Key West with its vibrant atmosphere and historic architecture. Visitors will find themselves within walking distance of iconic attractions such as the Ernest Hemingway Home and Museum, where they can explore the life and works of the famed author, and the lively Duval Street, known for its shops, bars, and restaurants.
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 travelling 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.
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, travellers should focus on the vibrant areas near the southernmost point of the continental United States. The stretch along South Beach is particularly popular, offering a selection of beachfront properties with stunning ocean views and direct access to the sandy shores. Many of these houses come equipped with amenities such as private pools, outdoor seating areas, and fully stocked kitchens, making them superb for families or groups looking to enjoy a seaside retreat.

Another excellent location is the area around Fort Zachary Taylor Historic State Park. Here, visitors can find charming beach cottages and larger homes that often feature wrap-around porches, barbecue facilities, and lush gardens for a bit of added privacy. The proximity to the park provides opportunities for swimming, picnicking, and exploring the historic fort, enhancing the vacation experience. Find your rental near the beach in Key West.
Are there any houseboat rentals in Key West?
Yes, you can find houseboat rentals in Key West, with approximately 53 available throughout the area. These unique accommodations are often located near the vibrant waterfront and close to popular attractions such as Mallory Square and Duval Street, making them ideal for experiencing the local culture. Most houseboats come equipped with essential amenities, including kitchens for preparing meals, comfortable living spaces, and outdoor decks for enjoying the stunning views of the ocean. 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 approximately 1,207 available throughout the area. These properties often feature spacious layouts, multiple bedrooms, and outdoor spaces such as patios or gardens, making them ideal for families or groups. Many houses also include fully equipped kitchens and comfortable living areas, allowing guests to enjoy a cozy feel while being close to attractions like the Ernest Hemingway Home and Museum, Mallory Square, and the vibrant nightlife of Duval Street.
Are there any family house rentals in Key West?
In Key West, there are a remarkable 1,350 family-friendly house rentals available, particularly in vibrant neighbourhoods like Old Town and New Town. Old Town properties often feature spacious living areas, private pools, and easy access to local attractions, including the Ernest Hemingway Home and Museum and the lively atmosphere of Duval Street—great for family outings. Guests can expect practical amenities such as fully equipped kitchens, outdoor grilling stations, and beach gear to enhance their stay.

Meanwhile, New Town offers larger accommodations with multiple bedrooms, expansive gardens, and entertaining spaces like game rooms and fenced yards. This area is also conveniently located near Bayview Park, which boasts playgrounds, sports courts, and picnic areas, making it ideal for families seeking outdoor activities. 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 feature pools and hot tubs, with around 1,765 options to choose from. This charming island city is known for its vibrant atmosphere and beautiful beaches, making it a popular destination for travellers.

You can find these properties in various neighbourhoods, including the historic Old Town, which is close to famous landmarks and lively nightlife, as well as the quieter areas like New Town, which offer a more relaxed setting. Many rentals come equipped with private pools, inviting hot tubs, outdoor patios for al fresco dining, and fully equipped kitchens, making them superb for families or groups looking to unwind after a day of exploring. 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. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Key West?
In Key West, there are numerous pet-friendly house rentals available, with around 864 options to choose from. Many of these properties are situated in close proximity to the picturesque beaches and vibrant local culture, making them ideal for travellers with pets. Vacation rentals often come equipped with amenities such as private pools, outdoor seating areas, and fully equipped kitchens, ensuring a comfortable stay for both humans and their furry companions.

The area around Duval Street is particularly lively, offering a range of dining and entertainment options that welcome pets, including outdoor patios and pet-friendly cafes. Additionally, the nearby Higgs Beach features a pet-friendly area where dogs can enjoy the sand and sea, providing a great outing for your pet after exploring the charming streets of Key West. 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 tailored for remote work, with around 2,184 options available. This vibrant island offers a unique blend of relaxation and productivity, making it an ideal destination for those looking to balance work and leisure. Many properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated office spaces, desks, and comfortable desk chairs, ensuring a conducive working environment. Additionally, some rentals may provide extra features like safes and computer monitors for added convenience. 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 travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Key West?
In Key West, popular rental amenities include kitchens, allowing guests to prepare their own meals, and complimentary Wi-Fi, which is essential for staying connected. Many vacation rentals also feature shared pools, with some offering heated options for a more comfortable swim experience.
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. During these months, the island buzzes with activity, drawing visitors who are eager to experience its vibrant culture, stunning sunsets, and outdoor adventures. The weather is typically warm and inviting, with daytime temperatures reaching the low 20s Celsius, making it ideal for beach outings and water sports.

Key West is particularly lively in March, with events like Fantasy Fest and the annual Hemingway Days, providing unique opportunities for sightseeing and local festivities. The pleasant climate encourages outdoor dining, leisurely strolls along the historic streets, and enjoying the natural beauty of the nearby coral reefs.

For those looking for a more budget-friendly experience, consider visiting in October. This month offers a quieter atmosphere, allowing for a more relaxed exploration of the island's charming attractions, such as the Ernest Hemingway Home and Museum or the iconic Duval Street. Despite being outside the peak season, October still boasts warm temperatures and fewer crowds, making it a wonderful time to appreciate the local culture and enjoy outdoor activities at a more leisurely pace.
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 engage in a variety of attractions that showcase the island's unique charm. The historic Old Town is a must-visit, featuring the iconic Ernest Hemingway Home and Museum, where literature enthusiasts can explore the author's former residence. Nearby, the lively Duval Street offers a multitude of shops, bars, and restaurants, providing a great spot for evening entertainment and dining.

For those interested in maritime history, the Key West Shipwreck Museum is an intriguing stop, showcasing the island's seafaring past. Additionally, the southernmost point buoy is a popular landmark, great for photo opportunities.

Nature lovers will appreciate the proximity to the Dry Tortugas National Park, accessible by ferry or seaplane, where stunning beaches and exceptional snorkeling await. The nearby Fort Zachary Taylor Historic State Park also offers beautiful waterfront views and picnic areas, making it an ideal spot to relax.
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 makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Key West 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.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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