Downtown Key West vacation rentals

We found 836 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Downtown Key West by choosing from 65 houses, 56 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 rental options are available, with several apartments, vacation houses, condos, and cottages dispersed throughout the area. These properties typically feature modern amenities such as fully equipped kitchens, comfortable living spaces, and outdoor patios or balconies, allowing guests to enjoy the vibrant island atmosphere. Many rentals are located within walking distance to popular attractions like Duval Street, the Ernest Hemingway Home and Museum, and the picturesque waterfront, making them convenient for visitors looking to explore.
Are there any beach house rentals in Downtown Key West?
In Downtown Key West, there are about 15 beach house rentals available, offering a great experience in this vibrant area known for its lively option and historical charm. Travelers can expect properties that feature multiple bedrooms, fully equipped kitchens, spacious living areas, and often outdoor patios or balconies great for enjoying the tropical climate. These rentals are ideally situated near popular points of interest such as Duval Street, the Ernest Hemingway Home and Museum, and the beautiful beaches of the area.
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 include fully equipped kitchens, allowing guests to prepare their own meals and enjoy dining in comfort. Many rentals also feature coffee and tea makers for a quick morning brew. For pet owners, several properties permit pets, making it easier to travel with furry companions. Outdoor spaces are common too, with decks or patios where guests can relax and soak in the tropical atmosphere. Additionally, many rentals are conveniently located near the sea, providing easy access to beach activities and stunning waterfront views.
Can I find family house rentals in Downtown Key West?
In Downtown Key West, there are several family-friendly house rentals available, making it an excellent choice for those traveling with children. This vibrant area is known for its bustling atmosphere and rich history. Visitors can expect spacious homes that often include amenities such as full kitchens, comfortable living rooms, and outdoor areas where families can relax and enjoy the warm weather.

These properties are conveniently located near popular attractions like the Key West Butterfly and Nature Conservatory and the iconic Southernmost Point buoy. Families can explore the nearby beaches or take a stroll along the scenic waterfront. Additionally, parks with playgrounds and picnic areas are just a short distance away, superb for kids to burn off energy.
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 feature both pools and hot tubs, making it an excellent choice for travelers seeking relaxation and comfort. This vibrant area is known for its lively option, historic architecture, and proximity to beautiful beaches. Many properties in Downtown Key West come equipped with private pools, inviting hot tubs, and outdoor spaces superb for enjoying the tropical climate.

Travelers can also expect amenities such as fully equipped kitchens, allowing for convenient meal preparation, as well as spacious living areas and patios or decks for entertaining. Additionally, some rentals may offer features like barbecue grills and easy access to local attractions, enhancing the overall vacation experience.
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.
Can I book pet-friendly vacation rentals in Downtown Key West?
In Downtown Key West, travelers can find a variety of pet-friendly vacation rentals, with around 11 options available. Many of these rentals are situated close to the vibrant setting of Duval Street, offering easy access to local shops, restaurants, and nightlife. Expect amenities such as private patios, outdoor spaces for pets, and fully equipped kitchens, which make for a comfortable stay.

The area is also near several parks and pet-friendly beaches, including Higgs Beach, where pets are welcome and can enjoy the sun and sand. The lush surroundings and nearby parks provide excellent opportunities for walking and outdoor activities with your furry companions.
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?
The best time to visit Downtown Key West for a vacation rental is during the peak season from January to March, with March being particularly popular. This vibrant period attracts travelers seeking warm weather and lively festivities. Visitors can indulge in a variety of outdoor activities, from snorkeling in the crystal-clear waters to exploring the charming streets lined with historic architecture and colorful shops.

During these months, temperatures typically range from the mid-60s to mid-80s Fahrenheit, offering a comfortable climate for sightseeing and beach activities. The bustling atmosphere is enhanced by events such as Fantasy Fest and the Key West Literary Seminar, making it an ideal time for those who appreciate culture, entertainment, and social experiences.

For those looking for a more budget-friendly option, consider visiting in October. While it is outside the peak season, October still offers pleasant weather and fewer crowds, allowing for a more relaxed exploration of the island. This time is great for enjoying the local cuisine at quieter restaurants or taking leisurely walks along the waterfront.

Ultimately, your ideal visit to Downtown Key West will depend on whether you prefer the lively energy of peak season or the tranquil charm of the shoulder months.
Are there any remote work vacation rentals in Downtown Key West?
In Downtown Key West, there are several remote work vacation rentals available, with around 18 options to choose from. This vibrant area is known for its lively option, historic architecture, and close proximity to stunning beaches and popular attractions like the Ernest Hemingway Home and Museum and Mallory Square. Many of the vacation rentals in this region come equipped with essential amenities for remote work, including high-speed internet and Wi-Fi, dedicated desk spaces, and comfortable living areas designed to facilitate productivity.

Travelers can expect to find properties featuring fully equipped kitchens, allowing for convenient meal preparation, as well as outdoor spaces where one can relax after a day of work. 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, Florida, United States of America?
In Downtown Key West, visitors can experience firsthand a vibrant blend of history, culture, and stunning waterfront views. One of the most famous attractions is the Ernest Hemingway Home and Museum, where travelers can explore the author's former residence and its lush gardens. Just a short walk away is the iconic Duval Street, a bustling thoroughfare lined with shops, restaurants, and lively bars, great for those looking to experience the local nightlife and cuisine.

The southernmost point buoy, marking the southernmost point in the continental United States, is another must-see landmark that draws many visitors for photo opportunities. Nearby, Mallory Square is renowned for its sunset celebrations, where locals and tourists alike gather to enjoy street performances and breathtaking views of the sunset over the Gulf of Mexico.

Additionally, the Key West Butterfly and Nature Conservatory offers a tranquil escape with beautiful butterflies fluttering in a lush, climate-controlled environment. For beach lovers, the nearby Fort Zachary Taylor State Park provides a picturesque spot for swimming and sunbathing, along with historical fortifications to explore.
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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