Truman Annex vacation rentals

We found 1,317 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Truman Annex by choosing from 114 houses, 159 condos, and other vacation rentals. Whether you’re staying in a vacation home with friends, family, or even just your pets, you'll find the amenities you need and want, which might include WiFi and a washer and dryer. Whatever you're looking for, you'll be able to choose a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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Find out more about Truman Annex

Why visit Truman Annex

  • Rich history: Explore historic houses and sites that reflect Key West's unique past.
  • Waterfront attractions: Enjoy stunning ocean views and access to various water activities.
  • Vibrant local atmosphere: Experience the lively streets and cultural offerings of the neighborhood.
  • Family-friendly experiences: Engage in activities suitable for visitors of all ages, ensuring fun for everyone.
  • Diverse accommodation options: Choose from private homes, condos, and cozy cottages for a perfect stay.

Popular types of accommodation around Truman Annex

Discover the charm of Truman Annex with our selection of vacation rentals, including private homes, condos, and cozy cottages. Whether you're seeking a spacious family retreat or a romantic getaway, our Key West rentals cater to every traveler's needs. Enjoy transparency and reassurance as you find the perfect Truman Annex vacation rental for your next holiday. Start your adventure in this vibrant community today.

  • Houses: The top choice for travelers in Truman Annex, these homes offer spacious living and a home-like atmosphere, perfect for families or groups.
  • Condos: Popular for their modern amenities and convenient locations, condos provide a comfortable stay with easy access to local attractions.
  • Cottages: Charming and cozy, cottages in Truman Annex are ideal for those seeking a quaint retreat close to the beach.
  • Apartments: A practical option for visitors, apartments offer flexibility and comfort, making them great for longer stays.
  • Villas: Luxurious and spacious, villas provide a high-end experience for those looking to indulge during their vacation.**

Top attractions near Truman Annex

Truman Annex is a fantastic destination for city-themed, family, and business vacations. Visitors can explore a variety of attractions, including historic houses, vibrant streets, and modern squares. With its rich cultural offerings and family-friendly experiences, Truman Annex caters to travelers seeking to immerse themselves in the local atmosphere and history. Make sure to take time to enjoy the unique charm of this Key West gem.

  • Duval Street: A vibrant thoroughfare filled with lively shops, restaurants, and bars. Experience the energetic atmosphere, enjoy live music, and indulge in delicious local cuisine, all while soaking in the unique character of Key West.
  • Mallory Square: Known for its stunning sunset views, this bustling square is the perfect spot to unwind. Enjoy street performances, local art vendors, and the festive ambiance as the sun sets over the Gulf of Mexico.
  • Ernest Hemingway Home and Museum: Step into literary history at the former residence of Ernest Hemingway. Explore the beautiful grounds and museum exhibits showcasing the author's life, works, and the famous six-toed cats that roam the property.

Things to do recommended for couples

Ready for a romantic getaway in Truman Annex? Explore the enchanting streets on a sunset bike ride or indulge in a candlelit dinner at a waterfront restaurant. Don't forget to catch a breathtaking sunset at Mallory Square for an unforgettable experience with your loved one.

Things to do recommended for families

Families vacationing in Key West can have a splashing good time at the MLK Community Pool & Community Center, located 0.7 miles from Truman Annex. With its vibrant sports atmosphere and family-friendly vibe, it's a perfect spot for fun and relaxation together.

Things to do recommended for groups

Enjoy a round of golf at the Key West Golf Club, only 4 miles from Truman Annex, or soak in a show at the nearby Waterfront Playhouse, just 0.4 miles away. Don't forget to stop by The Kite House, located 0.6 miles away, for unique local souvenirs.

*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 Truman Annex

If you're traveling with friends, family, pets, or planning an extended stay, be sure to use the appropriate filters to match your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Truman Annex with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Truman Annex with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Truman Annex: For many, a family vacation isn't truly fulfilling without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Many pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Truman Annex: 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 options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Truman Annex

Truman Annex offers a unique blend of tropical charm and historical allure in Key West, Florida. This beautiful neighborhood is perfect for family vacations and adventure seekers, with nearby waterfront attractions and a vibrant local atmosphere. Explore the stunning ocean views, immerse yourself in the rich history, and enjoy the laid-back lifestyle that defines this picturesque region. Whether you're seeking relaxation or excitement, Truman Annex and its surroundings promise unforgettable experiences.

  • Key West: Key West is a vibrant island city that captures the essence of Florida's laid-back lifestyle. Known for its beautiful beaches and welcoming atmosphere, it's a perfect spot for families and business travelers alike. The city boasts a variety of shopping areas and malls, alongside resorts that cater to diverse preferences. Visitors can explore the scenic waterfront, unwind on family-friendly beaches, and stroll through colorful streets filled with local shops and eateries. Key West is an ideal destination for those looking to enjoy a mix of relaxation and adventure in a picturesque setting.
  • Old Town Key West: Located just 0.7 miles from Truman Annex, Old Town Key West is renowned for its charming streets and historical significance. This neighborhood offers a delightful blend of city life and family-friendly activities, making it a popular choice for tourists. Old Town features a variety of shopping options, including unique boutiques and art galleries. Visitors can enjoy leisurely walks along the streets, relax on the beach, or indulge in the local dining scene. Its proximity to major attractions makes it a convenient and enjoyable area to explore.
  • Key West Historic District: The Key West Historic District is situated a mere 0.6 miles from Truman Annex and is rich in cultural heritage. This neighborhood showcases the island's unique architecture and history, making it a great spot for sightseeing. Travelers will find a mix of shopping areas, resorts, and delightful streets lined with beautiful homes. The district is also close to scenic beaches, perfect for families looking to soak up the sun. Whether you're interested in history or simply want to enjoy the vibrant local culture, the Historic District offers an enchanting experience.

Best time to go to Truman Annex

If you're planning a trip to Truman Annex, 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

Are you hoping to cut costs on your upcoming adventure? Being flexible with your travel dates can really help, as prices often vary. Additionally, opting for a longer stay can lead to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you make the most of your travel experience.

Save more with One Key

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

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a user-friendly platform where you can effortlessly plan new trips, resume your previous arrangements, or manage your travel itinerary. You can easily find your saved or booked properties organized under categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Truman Annex?
In Truman Annex, condos are a popular choice among vacation rentals, with several available throughout this charming neighborhood. These condos typically feature modern amenities, including fully equipped kitchens, comfortable living spaces, and often private balconies or patios that allow guests to enjoy the warm Florida weather. The area is known for its proximity to key attractions such as the Ernest Hemingway Home and Museum and the lively Duval Street, making condos a convenient option for travelers looking to explore. Additionally, several vacation houses are offered, providing more spacious rooms ideal for families or larger groups, complete with outdoor areas for relaxation.
Are there any beach house rentals in Truman Annex?
In Truman Annex, there are several beach house rentals available, making it a popular choice for those looking for a coastal getaway. These beach houses are typically situated in close proximity to attractions such as the historic district of Key West and the vibrant nightlife along Duval Street. Travelers can expect amenities like spacious living areas, fully equipped kitchens, private outdoor spaces for relaxing, and often access to communal pools. The area offers a laid-back atmosphere, great for families or groups seeking a memorable vacation experience by the sea.
How much does it cost to rent a vacation home in Truman Annex?
Prices for vacation rentals in Truman Annex 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 Truman Annex 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 Truman Annex vacation house rentals?
You can find great discounts on house rentals in Truman Annex 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 Truman Annex?
In Truman Annex, popular rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals, along with coffee and tea makers for a convenient start to the day. Many rentals feature outdoor spaces such as decks or patios, superb for enjoying the pleasant Florida weather. Onsite parking is also a common amenity, providing easy access for those traveling by car.
Can I find family house rentals in Truman Annex?
In Truman Annex, a charming neighborhood in Key West, several family-friendly vacation homes are available. This area is known for its vibrant setting and proximity to local attractions, making it an ideal spot for families. Properties often come with spacious living areas, fully equipped kitchens for easy meal preparation, and outdoor spaces for children to enjoy.

Visitors can relish the nearby sights, such as the historic sites of Old Town and the lively ambiance of Duval Street, which is just a short walk away. Moreover, many rentals feature amenities like private patios or balconies, superb for relaxing after a day of exploring.
Can I rent a vacation home with a pool or hot tub in Truman Annex?
In Truman Annex, Florida, travelers will find several vacation homes available for rent that feature both pools and hot tubs. This charming neighborhood, located adjacent to the vibrant culture of Key West, provides a unique blend of relaxation and recreation. Many of the rentals come with private pools, inviting hot tubs, and outdoor spaces ideal for lounging or entertaining.

Amenities typically include fully equipped kitchens, spacious living areas, and access to vibrant local attractions, making it a great choice for families or groups looking to enjoy a sunny getaway.
Are there any Truman Annex vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Truman Annex 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 Truman Annex?
Yes, you can book pet-friendly vacation rentals in Truman Annex. This charming neighborhood in Key West offers several vacation rentals that welcome pets, making it a great destination for travelers who wish to bring their furry companions along. Many of these rentals come equipped with amenities such as private patios, outdoor spaces for your pets to enjoy, and comfortable living areas that allow for a relaxing stay.

The area is known for its proximity to various parks and green spaces where you can take your pets for walks. Additionally, the vibrant local atmosphere includes pet-friendly cafes and shops, enhancing your experience while exploring the neighborhood. See all pet-friendly rentals in Truman Annex.
Can I find long-stay vacation rentals in Truman Annex?
A long-stay vacation rental in Truman Annex 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 Truman Annex for a vacation rental?
March is the most popular month to visit Truman Annex, attracting a vibrant crowd eager to soak up the sun and enjoy the beautiful beaches. The peak season runs from January to March, where visitors can experience the lively option and partake in a variety of outdoor activities, including water sports, snorkeling, and exploring the nearby vibrant nightlife.

During this peak season, temperatures in Truman Annex typically range from the mid-60s to the low 80s Fahrenheit, creating a comfortable environment for both sunbathing and sightseeing. While the beaches are bustling with activity, you can also find charming spots for a leisurely stroll, all set against the picturesque backdrop of the Florida Keys.

For those looking to travel on a budget, October presents a wonderful opportunity to visit. This month allows you to enjoy the area in a more tranquil setting, with fewer crowds and the added beauty of the fall season. The weather remains warm but with less tourist activity, making it ideal for exploring the local culture and enjoying the natural beauty without the hustle and bustle.

Ultimately, your superb time to visit Truman Annex will depend on whether you seek the energetic atmosphere of peak season or the peaceful charm offered in the quieter months.
Are there any remote work vacation rentals in Truman Annex?
In Truman Annex, Florida, there are several vacation rentals suitable for remote work. This charming neighborhood offers a unique blend of historical charm and modern amenities, making it an appealing destination for those looking to combine work and leisure. Many properties in the area provide essential remote work amenities such as reliable Wi-Fi, allowing guests to stay connected while enjoying their vacation.

Accommodations often feature comfortable living spaces equipped with work-friendly setups, and some may offer additional conveniences like internet access in public areas and event-friendly policies. The proximity to local attractions such as the vibrant nightlife of Duval Street and the beautiful beaches of Key West enhances the experience, providing ample opportunities for relaxation after a productive workday. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Truman Annex vacation rental?
Book your Truman Annex 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 Truman Annex, Florida, United States of America?
In Truman Annex, visitors can enjoy a blend of historical charm and modern attractions. The neighborhood is adjacent to the historic district of Key West, allowing easy access to prominent sites like the Ernest Hemingway Home and Museum, where the famous author lived and wrote. Nearby, the Key West Lighthouse offers panoramic views of the island.

For those interested in the arts, the Key West Theatre hosts various performances and events throughout the year. The Truman Annex area itself is known for its picturesque, tree-lined streets and beautiful architecture, making it great for leisurely strolls.

Additionally, the proximity to the beach allows travelers to enjoy the sandy shores and warm waters, with popular spots like Fort Zachary Taylor State Park offering opportunities for swimming and picnicking.
Can I change or cancel my Truman Annex home rental booking on Vrbo?
To find Truman Annex 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 Truman Annex 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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