Downtown Key West vacation rentals

We found 849 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Downtown Key West by choosing from 70 houses, 60 apartments, and other vacation rentals. Whether you're traveling with family, friends, or just your furry companion, vacation homes have the amenities you expect for your stay, such as air conditioning and WiFi. No matter what you're looking for, you'll find a rental for everyone's needs, including a place that is accessible or non-smoking.

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Find out more about Downtown Key West

Why visit Downtown Key West

  • Rich History: Explore the Key West Historic District, filled with iconic landmarks and charming streets that tell the story of the island.
  • Breathtaking Mallory Square: Experience the vibrant atmosphere at Mallory Square, renowned for its sunset celebrations and lively street performances.
  • Tropical Charm: Enjoy the picturesque architecture and tropical ambiance that make Downtown Key West a unique destination.
  • Diverse Accommodations: Choose from a variety of vacation rentals, from cozy cottages to luxurious condos, tailored to fit any budget.
  • Family-Friendly Activities: Engage in a range of activities suitable for all ages, ensuring fun for the entire family.

Popular types of accommodation around Downtown Key West

Planning a getaway to Downtown Key West? You're in for a treat. Discover the charm of this vibrant area with our top-notch vacation rentals. From cozy houses to stylish condos and charming cottages, we have the perfect accommodation to suit your needs. Enjoy the convenience of downtown living while being just minutes from beautiful beach rentals. Your ideal Key West vacation starts here.

  • Houses: These spacious rentals are the top choice in Downtown Key West, perfect for families or groups seeking comfort and privacy.
  • Condos: A popular option for travelers, condos offer modern amenities and often feature stunning views of the ocean.
  • Cottages: Quaint and charming, cottages provide a cozy atmosphere for a relaxing getaway.
  • Apartments: Ideal for couples or solo travelers, apartments offer convenience and easy access to local attractions.
  • Villas: Luxurious and spacious, villas cater to those looking for an upscale vacation experience in Key West.**

Top attractions near Downtown Key West

Downtown Key West is perfect for family, business, and city-themed vacations, offering a blend of culture and history. Explore the Key West Historic District, iconic landmarks, and charming streets. With various vacation rentals available, you can find options that fit your budget. Whether you’re seeking family-friendly activities or unique vacation ideas, Downtown Key West provides a delightful experience for every traveler.

  • Duval Street: Experience the lively atmosphere of Duval Street, lined with vibrant shops, bars, and restaurants. This iconic street is perfect for strolling, people-watching, and enjoying the local nightlife, all while soaking in the unique island vibe.
  • Southernmost Point: Visit the famous Southernmost Point buoy, a must-see landmark marking the southernmost tip of the continental United States. Capture photos with this iconic symbol while enjoying the rich cultural history of Key West.
  • Ernest Hemingway Home and Museum: Explore the historic residence of renowned author Ernest Hemingway. This beautifully preserved house offers a glimpse into his life, showcasing unique architecture, lush gardens, and a fascinating collection of artifacts.

Things to do recommended for couples

Ready for a romantic getaway in Downtown Key West? Stroll hand-in-hand along the picturesque streets, savor a sunset sail on a catamaran, or indulge in a candlelit dinner at a waterfront restaurant. Don’t miss the lively atmosphere of Mallory Square as the sun sets over the horizon.

Things to do recommended for families

Families exploring Downtown Key West can take a refreshing dip at the MLK Community Pool & Community Center, located 0.3 miles away. This welcoming spot offers a fun atmosphere with sports and outdoor activities, perfect for enjoying quality time together.

Things to do recommended for groups

Groups visiting Downtown Key West can enjoy a round of golf at the Key West Golf Club, catch a performance at the Waterfront Playhouse, or shop for unique items at The Kite House, all while soaking in the vibrant local culture and outdoor atmosphere.

*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 around Downtown Key West

When traveling with a group, family, pets, or planning for an extended stay, it's important to use the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Downtown Key West with a group: Think about how many bedrooms you’ll require, as well as features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Downtown Key West with young kids: Traveling with young kids can present some challenges. It's important to prioritize their comfort and safety, along with amenities that are suitable for their age, 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 Downtown Key West: For many families, a vacation isn't truly fulfilling without their furry friend by their side. If you can relate, take a look at Vrbo listings that welcome pets. Most of these pet-friendly homes come equipped with feeding bowls and pet beds, ensuring that everyone feels comfortable and at ease.
  • Planning for a long term stay visiting Downtown Key West: If you're in search of vacation rentals offering discounts for 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 include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Downtown Key West

Downtown Key West offers a vibrant mix of history, adventure, and tropical charm. Explore the historic downtown area with its colorful architecture and lively atmosphere, perfect for family vacations or solo adventures. Discover key attractions like the famous Mallory Square and indulge in a luxury Key West experience. Whether you're seeking relaxation or exciting excursions, Downtown Key West promises a perfect getaway filled with unforgettable memories.

  • Key West: Key West is a vibrant island city renowned for its laid-back atmosphere and stunning coastal views. Located at the southernmost point of the continental United States, it is a prime destination for family vacations, business trips, and city-themed experiences. In Downtown Key West, visitors can explore a variety of shopping areas and resort options, all within walking distance. Local landmarks include beautiful beaches and lively streets that offer a unique blend of culture and relaxation. Enjoy the family-friendly beaches or take a leisurely stroll through the bustling downtown, where you'll find an array of restaurants and bars that showcase the island's famous nightlife.
  • Old Town Key West: Situated a mere 0.2 miles from Downtown Key West, Old Town Key West is a charming neighborhood that captures the essence of island life. Visitors flock here for its rich history and vibrant atmosphere, perfect for family outings and business gatherings alike. Old Town is home to a variety of shopping areas and resorts, making it an ideal spot for leisurely exploration. Visitors can enjoy scenic streets lined with local shops and cafes, as well as proximity to picturesque beaches, perfect for a family day out or a relaxing afternoon by the water.
  • Key West Historic District: Located 0.3 miles from Downtown Key West, the Key West Historic District is a treasure trove of architectural beauty and culture. This neighborhood invites travelers interested in city-themed experiences and family-friendly adventures. Here, you can find an array of shopping areas and quaint resorts nestled among the historic buildings. The district is dotted with charming streets, inviting beaches, and family-friendly beach spots, making it an excellent destination for history buffs and casual explorers alike. Take a leisurely walk and soak in the rich heritage that this area has to offer.

Best time to go to Downtown Key West

If you're planning a trip to Downtown Key West, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from January to March, while off-peak times, like August to October tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January71.1°F (21.7°C)No Rain (Dry)Mostly SunnySlightly HighAverage
February72.1°F (22.3°C)No Rain (Dry)Mostly SunnySlightly HighAverage
March73.4°F (23.0°C)No Rain (Dry)Mostly SunnySlightly HighSlightly High
April76.8°F (24.9°C)No Rain (Dry)Mostly SunnyAverageSlightly High
May79.3°F (26.3°C)Light RainMostly SunnyAverageAverage
June82.6°F (28.1°C)Light RainMostly SunnyAverageSlightly Low
July84.0°F (28.9°C)Light RainMostly SunnyAverageAverage
August84.4°F (29.1°C)Light RainMostly SunnySlightly LowSlightly Low
September83.7°F (28.7°C)Light RainMostly SunnySlightly LowSlightly Low
October80.8°F (27.1°C)Light RainMostly SunnySlightly LowAverage
November76.6°F (24.8°C)Light RainMostly SunnyAverageAverage
December73.9°F (23.3°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and rental type.

Unlock savings with One Key

When you reserve an eligible Vrbo for your group getaway, you’ll earn OneKeyCash on your total booking amount. Being the organizer certainly has its perks. Enroll in our One Key rewards program to unlock exclusive savings for members and accumulate OneKeyCash on qualifying stays. Sign up today and begin reaping the benefits.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board is designed to help you plan your travels with ease. You can create new trips, continue with your existing plans, and manage your bookings all in one place. Your saved or booked properties are conveniently organized into categories: Potential, Upcoming, or Current Trips. To check out the Trip Boards, simply go to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Downtown Key West?
In Downtown Key West, a variety of vacation rentals are available, including apartments, vacation houses, condos, and cottages, with several options for each type. Many of these properties are situated within walking distance of popular attractions such as Duval Street, the Ernest Hemingway Home and Museum, and the vibrant waterfront. Typically, travelers can expect amenities like fully equipped kitchens, outdoor patios or balconies, and access to community pools. For those looking for more space, vacation houses often feature multiple bedrooms, private gardens, and BBQ facilities, making them ideal for families or groups.
Are there any beach house rentals in Downtown Key West?
In Downtown Key West, there are about 21 beach house rentals available, primarily situated close to the lively Duval Street and the historic waterfront. These beach houses typically offer a unique blend of tropical charm and modern amenities, including private pools, spacious patios, and outdoor dining areas superb for enjoying the warm Florida evenings. Inside, travelers can expect fully equipped kitchens, comfortable living spaces, and multiple bedrooms, making them ideal for families or groups. The proximity to popular attractions like the Ernest Hemingway Home and Museum and the iconic Southernmost Point Buoy adds to the appeal, allowing guests to immerse themselves in the vibrant local culture.
How much does it cost to rent a vacation home in Downtown Key West?
Prices for vacation rentals in Downtown 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 Downtown 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 Downtown Key West vacation house rentals?
You can find great discounts on house rentals in Downtown 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.
What are popular rental amenities in Downtown Key West?
In Downtown Key West, popular rental amenities often include fully equipped kitchens, which allow travelers to prepare their own meals and enjoy a home-like experience. Many properties feature heated pools, providing a comfortable swimming option year-round. Patios are common as well, offering outdoor spaces for relaxation and social gatherings, while coffee and tea makers are typically included for those who enjoy a warm beverage in the mornings. Additionally, many rentals are located near the sea, enhancing the appeal for guests looking to enjoy the beach and water activities.
Are there any family house rentals in Downtown Key West?
In Downtown Key West, several family-friendly house rentals are available, making it a great spot for families to enjoy their vacation. The area is known for its vibrant atmosphere and proximity to attractions like the Southernmost Point Buoy and the Key West Butterfly and Nature Conservatory. Many properties in this locale offer spacious living areas, fully equipped kitchens for easy meal preparation, and outdoor spaces where kids can play or families can gather for barbecues.

Additionally, some homes feature amenities such as private pools or game rooms, providing entertainment for all ages. With the beach and local parks just a short stroll away, visitors will find plenty of opportunities for outdoor fun.
Can I rent a vacation home with a pool or hot tub in Downtown Key West?
In Downtown Key West, there are several vacation homes available for rent that include both pools and hot tubs, with around 10 options to choose from. This lively and picturesque area offers a unique blend of vibrant nightlife, historic architecture, and beautiful waterfront views. Many of the properties feature private pools, superb for cooling off after a day of exploring, as well as hot tubs that provide a relaxing retreat in the evenings.

Travelers can expect amenities such as spacious outdoor areas, fully equipped kitchens, and comfortable living spaces, making them ideal for families or groups.
Are there any Downtown Key West vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Downtown 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.
Are there pet-friendly vacation rentals in Downtown Key West?
In Downtown Key West, travelers can find a variety of pet-friendly vacation rentals, with around 13 options available. This vibrant area is known for its lively atmosphere, historic charm, and close proximity to beautiful beaches. Many of the rental properties come equipped with desirable amenities such as private patios, outdoor seating areas, and full kitchens, making them suitable for families or groups traveling with pets.

The neighborhood offers easy access to several parks and green spaces, great for walks and outdoor playtime with furry companions. Notable nearby spots include the iconic Mallory Square with its stunning sunset views and the tranquil Fort Zachary Taylor Historic State Park, which features sandy beaches and picnic areas, ideal for a day out with your pet. Additionally, Downtown Key West boasts numerous pet-friendly cafes and shops, enhancing the overall experience for pet owners.
Can I find long-stay vacation rentals in Downtown Key West?
A long-stay vacation rental in Downtown 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.
When is the best time to visit Downtown Key West for a vacation rental?
March is the most popular time to visit Downtown Key West, as the vibrant atmosphere draws travelers seeking a mix of relaxation and adventure. The peak season runs from January to March, when visitors flock to the island for its warm, sunny weather and a lively calendar of events, including the famous Fantasy Fest and various outdoor activities such as snorkeling and sailing.

During this peak season, daytime temperatures typically range from the mid-70s to the low 80s Fahrenheit, providing an ideal climate for exploring the historic streets, indulging in fresh seafood, or lounging on the beautiful beaches. The bustling energy of the island during these months is superb for those looking to socialize and immerse themselves in local culture.

For travelers in search of more budget-friendly options, consider visiting in October, when the crowds thin out and you can enjoy a more tranquil experience. This month still offers pleasant temperatures, typically in the mid-70s to low 80s, allowing for comfortable outdoor exploration without the hustle and bustle of peak season. Plus, October is a great time to enjoy the natural beauty of the area, with fewer tourists and a chance to discover hidden gems at your own pace.

Ultimately, the best time for your vacation rental in Downtown Key West depends on whether you prefer the lively peak season filled with events and activities or a quieter getaway that lets you soak in the charm of this unique destination.
Are there any remote work vacation rentals in Downtown Key West?
In Downtown Key West, there is a solid selection of remote work vacation rentals, with around 21 options available. This vibrant area is known for its historic charm, colorful architecture, and close proximity to popular attractions such as Duval Street and the Ernest Hemingway Home and Museum. Travelers can expect rentals equipped with essential remote work amenities, including reliable Wi-Fi, dedicated office spaces or desks, and comfortable living areas that make it easy to balance work and leisure.

Many of these properties feature inviting outdoor spaces, such as patios or balconies, allowing for a refreshing break during work hours. Additionally, the proximity to local cafes and restaurants means that you can enjoy a change of scenery while working. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Downtown Key West vacation rental?
Book your Downtown 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 Downtown Key West?
In Downtown Key West, visitors can immerse themselves in a vibrant atmosphere filled with unique attractions. The famous Duval Street is a bustling hub known for its lively bars, lively shops, and local restaurants, making it a prime location for vacation rentals. Nearby, the Ernest Hemingway Home and Museum offers a glimpse into the life of the iconic author, surrounded by lush gardens and historical charm.

The southernmost point in the continental United States, marked by a colorful buoy, is also a must-visit site, providing an excellent photo opportunity. For those interested in maritime history, the Key West Shipwreck Museum presents fascinating exhibits just a short walk from the waterfront. Additionally, the picturesque Mallory Square is known for its evening sunset celebrations, where visitors can enjoy street performances and local food vendors.
Can I change or cancel my Downtown Key West home rental booking on Vrbo?
To find Downtown 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 Downtown 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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