Truman Annex vacation rentals

We found 1,327 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Truman Annex by choosing from 140 houses, 152 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

  • Historic charm: Explore the rich history of Truman Annex with its beautifully preserved historic houses and architecture.
  • Tropical adventure: Enjoy nearby beaches and lush surroundings, perfect for relaxation and outdoor activities.
  • Local culture: Immerse yourself in the vibrant local culture through arts, dining, and community events.
  • Diverse accommodations: Choose from a variety of vacation rentals, including private homes, condos, and charming cottages.
  • Family-friendly atmosphere: Truman Annex is ideal for families, offering a safe and welcoming environment for all ages.

Popular types of accommodation around Truman Annex

Discover the charm of Truman Annex in Key West with a variety of vacation rentals tailored to your needs. Whether you prefer a private vacation home, a cozy condo, or a quaint cottage, our selection offers something for every traveler. With transparent information and savings at your fingertips, finding the perfect Truman Annex rental is a breeze. Enjoy your getaway knowing you’ve made the right choice for a memorable stay.

  • Houses: The top choice for accommodations in Truman Annex, ideal for families, groups, or couples seeking a home-like atmosphere.
  • Condos: A popular option for visitors, offering a blend of comfort and amenities, perfect for a relaxed stay.
  • Cottages: Charming and cozy, these rentals provide a quaint escape in a picturesque setting.
  • Apartments: Convenient and well-equipped, making them a practical choice for shorter stays.
  • Villas: Luxurious and spacious, perfect for those looking for an upscale experience during their vacation.**

Top attractions near Truman Annex

Truman Annex is perfect for city-themed, family, and business vacations, offering a mix of historic houses, vibrant streets, and modern squares to explore. Visitors can immerse themselves in the local culture while enjoying various adventures that the area has to offer. Whether you're seeking relaxation or excitement, Truman Annex provides a delightful experience for all types of travellers.

  • Duval Street: A vibrant thoroughfare known for its lively atmosphere, Duval Street features an array of shops, bars, and restaurants, perfect for soaking in the local culture and nightlife.
  • Mallory Square: This bustling square is famous for its sunset celebrations, where locals and tourists gather to enjoy street performers, food vendors, and stunning views over the Gulf of Mexico.
  • Ernest Hemingway Home and Museum: A historic site showcasing the life and work of the famous author, visitors can explore the beautiful gardens and unique architecture, immersing themselves in literary history.

Things to do recommended for couples

Seeking a romantic getaway in Key West? Explore the picturesque Truman Annex on a sunset stroll, followed by a cozy dinner at a waterfront restaurant. Don’t miss a sunset sail for breathtaking views while sipping cocktails together. It's the perfect way to create unforgettable memories as a couple.

Things to do recommended for families

Families will love the MLK Community Pool & Community Center, located 1.1km from Truman Annex. This vibrant spot offers a refreshing pool, sports activities, and a welcoming atmosphere, perfect for enjoying quality time together in the beautiful Florida sunshine.

Things to do recommended for groups

Enjoy a round of golf at Key West Golf Club, just 6.4km from Truman Annex, or catch a show at the Red Barn Theater, a mere 483m away. Don’t forget to check out The Kite House, located 966m away, for unique local finds.

*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

When you're planning a trip, whether it's with a group, family, pets, or for an extended stay, it's important to prioritize your preferences in your search. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Truman Annex with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Truman Annex with young kids: Traveling with young children can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, you might want to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Truman Annex: For many, a family vacation wouldn’t feel complete without their furry companion. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels 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 consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay near Truman Annex

Truman Annex, a charming waterfront community in Key West, offers a delightful blend of tropical adventure and historical charm. Ideal for family getaways or business trips, this beautiful neighbourhood invites you to explore its lush surroundings and nearby beaches. Discover vibrant local culture, enjoy leisurely strolls, and unwind in this tropical retreat, where every corner holds the promise of a memorable experience. Don't miss out on the enchanting atmosphere that Truman Annex has to offer.

  • Key West: Key West is a vibrant city that serves as the southernmost point of the continental United States, beautifully situated on an island surrounded by the turquoise waters of the Gulf of Mexico. Known for its lively atmosphere, visitors flock to Key West for a variety of experiences including family-friendly outings, business retreats, and city adventures. The area is packed with activities such as shopping at local boutiques and malls, along with enjoying the beach and family-friendly waterfront. Key landmarks like the famous Duval Street and its picturesque beaches make it an ideal spot for relaxation and exploration.
  • Old Town Key West: Located 1.1km from Truman Annex, Old Town Key West is a charming neighbourhood that encapsulates the essence of island life with its historic architecture and vibrant culture. This area is perfect for tourists looking for a city-themed experience, family adventures, or business meetings. Old Town is replete with shopping areas and resorts, making it a convenient base for your vacation. Highlights include beautiful streets lined with palm trees, inviting beaches, and family-friendly spots that enhance the laid-back vibe of this unique locale.
  • Key West Historic District: Just 966m from Truman Annex, the Key West Historic District offers a glimpse into the island's rich past, with well-preserved Victorian homes and historic landmarks. This neighbourhood is a hotspot for those seeking a city-themed experience, family activities, or business environments. With easy access to shopping malls and resorts, visitors can enjoy leisurely strolls through its charming streets, relax on the local beaches, or engage in family-friendly festivities. Attractions in this area highlight the cultural heritage of Key West, making it an essential stop on your vacation.

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 save on your next getaway? Being flexible with your travel dates can lead to great savings, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even more significant discounts. To discover a Vrbo property that suits your budget, make use of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect spot for your travels.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, manage your existing arrangements, or review your bookings. Your saved or reserved properties are thoughtfully categorized into Potential, Upcoming, or Current Trips for easy organization. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/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 the area. These condos typically feature modern amenities such as fully equipped kitchens, spacious living areas, and balconies or patios that offer views of the lush surroundings. This makes them ideal for couples or small families looking for a comfortable stay close to attractions such as the historic Old Town and the vibrant nightlife of Duval Street.
Are there any beach house rentals in Truman Annex?
In Truman Annex, Florida, several beach house rentals are available, offering a charming escape near the vibrant heart of Key West. These properties typically feature multiple bedrooms, fully equipped kitchens, and spacious living areas, superb for families or groups. Many also include outdoor patios or decks, ideal for enjoying the warm Florida evenings. The neighbourhood is conveniently located near attractions such as the Ernest Hemingway Home and Museum and the beautiful beaches of Fort Zachary Taylor State Park, providing guests with both relaxation and cultural experiences.
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 travelling 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.
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 guests to prepare their own meals. Many properties feature heated pools, providing a comfortable swimming experience year-round, while some rentals also have shared pool access. Additionally, outdoor patios are common, offering a lovely space for relaxation and al fresco dining.
Are there any family house rentals in Truman Annex?
In Truman Annex, there are several family-friendly house rentals available, making it an excellent choice for families seeking a memorable getaway. This vibrant neighbourhood is located near the heart of Key West, offering easy access to attractions like the Southernmost Point Buoy and the lively atmosphere of Duval Street.

Properties in the area typically feature spacious living areas, full kitchens for family meals, and outdoor patios or balconies where guests can relax and enjoy the warm Florida weather. Many homes also come equipped with amenities such as Wi-Fi, air conditioning, and laundry facilities, ensuring a comfortable stay for everyone.
Can I rent a vacation home with a pool or hot tub in Truman Annex?
In Truman Annex, Florida, there are several vacation homes available for rent that feature both pools and hot tubs. This charming neighbourhood, located near the heart of Key West, offers a laid-back atmosphere with easy access to vibrant local attractions. Many of the properties come equipped with amenities such as private pools, inviting hot tubs, and outdoor spaces great for relaxation and socialising. Additionally, travellers can expect fully equipped kitchens and comfortable living areas, making these rentals ideal for families or groups looking to enjoy a memorable getaway in a tropical setting.
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 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.
Are there pet-friendly vacation rentals in Truman Annex?
In Truman Annex, there are several pet-friendly vacation rentals available that cater to travellers looking to enjoy a relaxing getaway with their furry companions. This charming neighbourhood is situated close to the vibrant heart of Key West, providing easy access to a variety of attractions and amenities. Many of the vacation rentals here come equipped with modern conveniences such as fully stocked kitchens, private patios, and some even feature outdoor spaces where pets can roam freely.
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. 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.
When is the best time to visit Truman Annex for a vacation rental?
The most popular time to visit Truman Annex is during the peak season from January to March, when the weather is pleasantly warm and the area comes alive with visitors eager to soak up the sun and enjoy outdoor activities. With average temperatures ranging from 20 to 26 degrees Celsius, this period provides ideal conditions for exploring the vibrant streets of Key West, lounging on beautiful beaches, or indulging in the local culinary scene.

March, in particular, stands out as a favourite month for travellers seeking a lively atmosphere. During this time, you can expect numerous events and festivals, including the famous Fantasy Fest, which adds an extra layer of excitement to your stay. The warm weather and festive spirit create a superb backdrop for outdoor adventures such as snorkelling, kayaking, and sailing.

For those looking to save a bit while still enjoying the charm of Truman Annex, October offers a wonderful alternative. The cooler temperatures, around 24 degrees Celsius, make for comfortable exploration without the hustle and bustle of peak season. This month is superb for enjoying quieter beaches, scenic bike rides, and the stunning sunsets that Key West is renowned for.
Are there any remote work vacation rentals in Truman Annex?
In Truman Annex, Florida, there are several vacation rentals that cater to remote workers, making it an excellent choice for those looking to blend work and leisure. These properties typically offer amenities such as reliable Wi-Fi, designated workspaces, and business centre access as part of the resort fee. Many rentals also provide additional comforts like safes for personal belongings, ensuring a secure environment for guests. 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?
In Truman Annex, visitors can explore a unique blend of history and vibrant culture. This charming neighbourhood, located adjacent to the famous Duval Street, offers easy access to attractions like the Ernest Hemingway Home and Museum, where fans of the author can delve into his life and works. The area is also close to the picturesque Fort Zachary Taylor State Park, known for its beautiful beaches and historical significance, great for sunbathing, picnicking, or exploring the fort itself.
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 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 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.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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