Photo by Rick Tuers

Truman Annex holiday homes

We found 1,253 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Truman Annex by choosing from 103 houses, 154 flats and other holiday rentals. Whether you’re staying in a holiday home with family or friends, you'll have the amenities that you expect and more, such as Wi-Fi and cable TV. At the end of the day, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Truman Annex

  • Historic charm: Wander through Truman Annex’s picturesque streets lined with historic houses, offering a glimpse into the vibrant past of Key West.
  • Cultural richness: Immerse yourself in the local atmosphere with a blend of history and modern charm, ideal for both family and business holidays.
  • Tropical adventure: Enjoy the nearby sun-kissed beaches and soak up the laid-back island lifestyle.
  • Vibrant community: Experience the lively local culture, with inviting modern squares and pleasant neighbourhood streets.
  • Memorable base: Use Truman Annex as your ideal hub to explore Key West’s diverse attractions and cultural delights.

Top attractions near Truman Annex

Truman Annex in Key West, Florida, is a vibrant neighbourhood steeped in history and culture, ideal for family and business-themed holidays. Visitors can explore charming historic houses, pleasant streets, and modern squares, all while soaking up the local atmosphere. The area offers a variety of experiences that cater to those seeking adventure and cultural enrichment, making it a perfect spot for a memorable holiday.

  • Duval Street: A vibrant thoroughfare, Duval Street is the heartbeat of Key West, brimming with shops, bars, and restaurants that exude lively city vibes, perfect for soaking in the local atmosphere.
  • Fort Zachary Taylor Historic State Park: This scenic park offers a blend of history and adventure, with outdoor activities like swimming and picnicking, set against the backdrop of a historic fort and lush surroundings.
  • Ernest Hemingway Home and Museum: Step into the world of literary icon Ernest Hemingway at his former residence. The museum showcases his life and work, enveloped in a rich cultural ambiance.

Things to do recommended for couples

Planning a romantic getaway in Truman Annex? Enjoy a sunset sail on the crystal-clear waters, explore the charming streets on bicycles, or unwind at a beachside café, sipping cocktails as the sun sets. These experiences will create unforgettable memories for you and your partner.

Things to do recommended for families

Families exploring Truman Annex can discover local art, enjoy waterfront walks, and savour delicious seafood at family-friendly spots, all within walking distance for a relaxed, immersive experience.

Things to do recommended for groups

Experience the vibrant local scene at Truman Annex with group-friendly activities like exploring art galleries, sampling fresh seafood, and enjoying sunset cruises around Key West’s historic streets.

*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 planning your trip—whether you’re travelling with a group, family, pets, or seeking longer stays—it's important to filter your options based on your priorities. 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 fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Truman Annex with young kids: Venturing out with young kids can be quite a task. It's important to prioritise their comfort and safety, along with suitable amenities 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 Truman Annex: For many families, a holiday isn’t truly fulfilling without their beloved four-legged companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Truman Annex: If you're after holiday rentals with discounts for month-long or longer stays, you're in the right spot. With the proper filter selection, you can effortlessly locate and save on monthly rentals. Don't forget to include extras like a parking space, a well-equipped kitchen, or a private pool in your search too.

Where to stay near Truman Annex

Truman Annex in Key West, Florida, offers a unique blend of historical charm and tropical adventure, making it perfect for family and business-themed holidays. Visitors can explore the picturesque streets, soak up the sun at nearby beaches, and enjoy the vibrant local atmosphere. With its rich history and proximity to attractions, Truman Annex provides an ideal base to experience the laid-back lifestyle and cultural delights of Key West.

  • Key West: Key West is a vibrant island city known for its unique blend of laid-back charm and bustling activity. Located at the southernmost point of the continental United States, it offers a perfect mix of family-friendly attractions and engaging city experiences. Visitors can enjoy shopping at local boutiques, dining at fresh seafood restaurants, or lounging on beautiful beaches. Key West is famous for its historic landmarks, such as the Ernest Hemingway Home and Museum and the iconic sunsets at Mallory Square, making it a must-visit destination for any traveller.
  • Old Town Key West: Situated just 1km from Truman Annex, Old Town Key West is a historic neighbourhood filled with charming streets and a rich maritime history. This area is ideal for those seeking a city-themed experience, with plenty of shopping areas and dining options. Visitors can explore the vibrant Duval Street, known for its lively atmosphere and eclectic shops. Old Town is also close to picturesque beaches, perfect for families looking to unwind and enjoy the sun.
  • Downtown Key West: Located a mere 805m from Truman Annex, Downtown Key West is the bustling heart of the city, offering a delightful blend of urban life and coastal serenity. This neighbourhood is popular for its shopping malls and local markets, making it a great spot for those looking to indulge in retail therapy. With easy access to beautiful beaches and family-friendly activities, Downtown Key West is an ideal area for both relaxation and exploration, showcasing the lively spirit of the island.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January71.1°F (21.7°C)No Rain (Dry)Mostly Sunny
February72.1°F (22.3°C)No Rain (Dry)Mostly Sunny
March73.4°F (23.0°C)No Rain (Dry)Mostly Sunny
April76.8°F (24.9°C)No Rain (Dry)Mostly Sunny
May79.3°F (26.3°C)Light RainMostly Sunny
June82.6°F (28.1°C)Light RainMostly Sunny
July84.0°F (28.9°C)Light RainMostly Sunny
August84.4°F (29.1°C)Light RainMostly Sunny
September83.7°F (28.7°C)Light RainMostly Sunny
October80.8°F (27.1°C)Light RainMostly Sunny
November76.6°F (24.8°C)Light RainMostly Sunny
December73.9°F (23.3°C)No Rain (Dry)Mostly Sunny

Booking with Vrbo is a breeze

Are you aiming to save on your next adventure? Being flexible with your travel dates can really pay off, as prices often vary. Additionally, opting for a longer stay typically results in significant savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of holiday rental. We're here to help you find the ideal getaway.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board gives you a dedicated space to start new journeys, pick up where you left off, or manage your bookings. Properties you’ve either saved or booked are neatly categorised into Potential, Upcoming, or Current Trips. To explore Trip Boards, head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday home accommodation in Truman Annex?
Condos are the most popular type of holiday home in Truman Annex, according to our data. Even if you've got something else in mind, Bookabach has properties in all sizes and shapes. Compare our options to find your perfect Truman Annex pad.
How much does it cost to rent a holiday home in Truman Annex?
Season, property type and length of stay are among the factors that can influence the price of a holiday home. Simply click on your travel dates to find the ultimate escape. From comfy cabins to expansive villas, all Bookabach holiday homes offer amazing value.
How much does it cost to rent a beach house in Truman Annex?
When you travel and the size and style of the property will help determine the cost of your beachside escape. Click on your Truman Annex travel dates to view your options on Bookabach. Can't live without a hot tub? Use our filters to pick the features and amenities you need.
Are there pet-friendly holiday homes in Truman Annex?
Pack a suitcase for your puppy dog because Truman Annex has 286 properties that welcome pets with open arms. Let your four-legged buddy join in on the family trip at one of our pet-friendly holiday homes on Bookabach. Simply enter your travel dates and destination, then check our "Pets allowed" filter box.
Can I rent a house with a pool in Truman Annex?
Add a whole new level of fun to your adventure by booking your crew into one of the 273 houses with a private pool in Truman Annex. Use our search filter to find the kind of property you want on Bookabach, and then spend your days splashing and playing in a swimming pool that's all your own.
What are popular home amenities in Truman Annex?
A garden, a swimming pool and a nearby waterfront rank as the most popular home amenities in Truman Annex. Whether you're taking to the road on your own, with your significant other or a group of best friends, Bookabach can help you find a holiday home that fits your style with all the features you're looking for.
Are there large group holiday homes in Truman Annex?
Truman Annex has two holiday homes that can accommodate 10 or more guests. These properties come with the space you need to share good times with friends and family.
Are there holiday homes in Truman Annex that welcome kids?
Truman Annex has 285 family-friendly holiday homes. And discovering a stay that welcomes kiddos is easy with Bookabach's "Properties good for families" filter. As well as having the whole place to yourselves, you can also look forward to perks and conveniences such as dining rooms, kitchens and yards.
What are the top attractions for families in Truman Annex?
Keeping the kids entertained during your stay in Truman Annex is simple with these leading family-friendly attractions:

  • Smathers Beach
  • South Beach
  • Higgs Beach

Are there one-bedroom holiday homes in Truman Annex?
Yes, there are 37 one-bedroom properties in Truman Annex to choose from. A one-bedroom holiday property is a great choice if it's only two of you or if you're travelling solo. Toss in more space, convenience and privacy compared to a standard hotel, and you've got yourself a getaway to remember.
Can I find two-bedroom holiday homes in Truman Annex?
Take off with your besties and enjoy total privacy and comfort in one of the 210 two-bedroom holiday homes Truman Annex has to offer.
Are there holiday homes with WiFi in Truman Annex?
Truman Annex has 113 holiday homes with WiFi, so you'll be able to stay connected during your holiday. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming Hollywood blockbusters to scrolling social media, these Bookabach homes make it a cinch to go online.
How can I find holiday homes with air conditioning in Truman Annex?
Work out your travel dates and then use the filters to view holiday homes with air conditioning in Truman Annex on Bookabach. With 252 air-conditioned properties available, you can look forward to a cool and comfortable stay.
How old do you have to be to rent a holiday home in Truman Annex?
We advise checking with the Truman Annex holiday home you'd like on Bookabach as the minimum age differs. However, normally it's 16, 18 or 21.
How long can I rent a holiday home in Truman Annex for?
It all depends on the Truman Annex property. To look over a list of options offering extended stays, simply type your travel dates and guest number into Bookabach. You can enjoy having the property to yourself, along with comforts such as a fully-equipped kitchen and outdoor spaces where the kids can run and play. Keep an eye out for long-term stays that offer weekly or monthly discounts.