Photo by Rick Tuers

Truman Annex holiday lettings

We found 1,251 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.

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Why visit Truman Annex

  • Historic Architecture: Stroll through Truman Annex to admire its charming historic houses that reflect the area’s rich past.
  • Scenic Streets: Enjoy walking along picturesque streets lined with lush greenery, perfect for a leisurely exploration.
  • Waterfront Access: Take advantage of the nearby beach access for relaxing by the water or indulging in water sports.
  • Cultural Experiences: Immerse yourself in the local culture with unique events and activities that showcase Key West's heritage.
  • Diverse Accommodations: Choose from various lodging options, including private homes and condos, catering to all preferences.

Popular types of accommodation around Truman Annex

Truman Annex in Key West, Florida, offers a charming blend of historic architecture and modern comfort. This picturesque neighbourhood is just a stroll away from stunning waterfront views, inviting parks, and vibrant local culture. Visitors can enjoy various accommodations, including houses, condos, and cottages. Whether you're seeking a tranquil retreat or an adventure-filled getaway, Truman Annex rentals provide the perfect base for exploring the unique experiences and attractions that Key West has to offer.

  • Houses: The top choice for visitors to Truman Annex, offering spacious and comfortable living with the convenience of a home away from home.
  • Condos: A popular option for those seeking modern amenities and a communal atmosphere, ideal for both relaxation and socialising.
  • Cottages: These charming abodes provide a quaint retreat, perfect for a peaceful getaway in a picturesque setting.
  • Apartments: A practical choice for travellers looking for convenience and accessibility in the heart of Key West.
  • Villas: Offering luxury and privacy, villas are ideal for those wanting a more upscale experience during their stay.**

Top attractions near Truman Annex

Truman Annex in Key West, Florida, is a vibrant neighbourhood ideal for city-themed, family, and business vacations. Visitors can explore historic houses, charming streets, and modern squares, immersing themselves in the local culture and adventure experiences. With its unique blend of history and urban charm, Truman Annex offers a delightful getaway that caters to a variety of interests and ensures memorable moments for all travellers.

  • Duval Street: A vibrant street known for its lively atmosphere, lined with shops, bars, and eateries, perfect for experiencing the local culture and nightlife.
  • Mallory Square: A bustling square famous for its sunset celebrations, offering street performers, local artisans, and stunning views of the Gulf of Mexico.
  • Fort Zachary Taylor Historic State Park: A historic fort set in a picturesque park, ideal for picnicking, swimming, and exploring nature trails amidst beautiful scenery.

Things to do recommended for couples

For a romantic getaway in Truman Annex, enjoy a sunset sail on the tranquil waters, explore the charming streets hand in hand, or indulge in a candlelit dinner at a seaside restaurant. Don't forget to visit the iconic sunsets at Mallory Square for a magical evening together.

Things to do recommended for families

Families visiting Truman Annex can enjoy a delightful day at the nearby Dry Tortugas National Park, where they can explore Fort Jefferson and snorkel in crystal-clear waters. Additionally, a visit to the Key West Butterfly and Nature Conservatory offers a magical experience among fluttering butterflies.

Things to do recommended for groups

Explore the vibrant streets of Old Town Key West, visit the Ernest Hemingway Home and Museum, or partake in a thrilling sunset sail. For those seeking adventure, try snorkelling or diving at the nearby coral reefs, perfect for group fun and bonding.

*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, as a family, bringing along pets, or seeking extended stays, it's important to refine your search according to your specific needs. Here are some helpful booking tips for Vrbo.

  • Traveling to Truman Annex with a group: Think about how many bedrooms you’ll require, as well as features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all of these options, and much more, on Vrbo.
  • Traveling to Truman Annex with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with suitable amenities, like a private swimming pool. Additionally, considering your closeness to family-friendly attractions is also advisable.
  • Taking your pets with you to Truman Annex: For many, a family holiday isn’t truly complete without their four-legged companion. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Truman Annex: If you're in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the perfect place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Truman Annex

Truman Annex in Key West, Florida, is a vibrant neighbourhood brimming with charm and history. This delightful area offers visitors a unique blend of tropical atmosphere and historical landmarks, perfect for family getaways or business trips. Explore the scenic streets lined with lush greenery, enjoy the nearby beach access, and immerse yourself in the rich cultural heritage. Whether you're seeking adventure or relaxation, Truman Annex is an ideal base for an unforgettable Key West experience.

  • Key West: Key West is a vibrant island city renowned for its laid-back atmosphere and stunning coastal views. As the southernmost point of the continental United States, it offers a unique blend of cultural experiences, from its historic architecture to lively nightlife. Popular activities include shopping at local boutiques, enjoying the beach, and exploring the rich history of the area. Key West is also home to notable landmarks such as the Ernest Hemingway Home and Museum and the famous Mallory Square sunset celebration, making it a perfect destination for families and business travellers alike.
  • Old Town Key West: Located a mere 1km from Truman Annex, Old Town Key West is a charming neighbourhood steeped in history and character. Visitors flock here for its picturesque streets lined with quaint shops, delightful dining options, and vibrant street life. The area boasts beautiful beaches and is ideal for families looking to soak up the sun or engage in local activities. Attractions such as the iconic Duval Street and the Southernmost Point Buoy are must-sees, making Old Town a perfect spot for both relaxation and exploration.
  • Downtown Key West: Just 805m from Truman Annex, Downtown Key West is the bustling heart of the island, offering an eclectic mix of shopping, dining, and entertainment. This neighbourhood is perfect for those seeking a vibrant urban experience, with numerous restaurants, bars, and shops to explore. Key landmarks include the Historic Seaport and various art galleries, all contributing to the area's lively atmosphere. Families and business visitors will appreciate the proximity to beautiful beaches and recreational activities, ensuring an enjoyable stay in this dynamic part of Key West.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 upcoming journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can achieve considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides you with a dedicated area to plan new journeys, refine your existing arrangements, or manage your bookings effectively. The properties you've saved or reserved are conveniently categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental in Truman Annex?
In Truman Annex, condos are the most popular type of holiday rental, with about 16 available in this charming community. These condos typically feature modern amenities such as fully equipped kitchens, comfortable living areas, and access to shared pools or outdoor spaces, making them ideal for couples or small families. Additionally, there are several holiday houses and apartments scattered throughout the area, offering a more spacious option for larger groups. These properties often come with multiple bedrooms, private outdoor areas, and convenient access to nearby attractions like the historic sites in Old Town Key West and the vibrant nightlife.
Are there any beach house rentals in Truman Annex?
In Truman Annex, several beach house rentals are available, providing a charming escape in this historic neighbourhood of Key West. These properties often feature spacious layouts, multiple bedrooms, and private outdoor spaces, allowing guests to enjoy the tropical atmosphere. Many beach houses come equipped with modern amenities such as fully stocked kitchens, comfortable living areas, and private pools or patios, superb for relaxation after a day of exploring nearby attractions like the Ernest Hemingway Home and Museum or the vibrant nightlife of Duval Street.
How much does it cost to rent a holiday home in Truman Annex?
Prices for holiday 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 holiday 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, and comfortable outdoor spaces such as decks or patios that are great for relaxing in the Florida sunshine. Many rentals also feature coffee and tea makers for a quick morning brew, and onsite parking is often available, making it convenient for those travelling with their own vehicles.
Can I find family house rentals in Truman Annex?
In Truman Annex, a charming neighbourhood of Key West, there are several family-friendly house rentals available. This area is known for its vibrant setting and proximity to attractions that cater to all ages. Many of the homes here offer spacious living areas, full kitchens, and private outdoor spaces where children can play.Visitors will appreciate the close access to nearby highlights such as the historic seaport and the famous Duval Street, filled with shops, restaurants, and entertainment options. Additionally, the nearby beaches provide excellent opportunities for family fun, whether it's swimming, sunbathing, or engaging in water sports.
Can I rent a holiday home with a pool or hot tub in Truman Annex?
In Truman Annex, Florida, there are several holiday homes available for rent that feature both pools and hot tubs. This charming neighbourhood, located near the vibrant heart of Key West, offers a unique blend of relaxation and adventure. Many of the properties in this area come equipped with private pools and hot tubs, providing the ideal setting for unwinding after a day of exploring the local attractions.Travellers can expect amenities such as spacious outdoor areas, fully equipped kitchens, and comfortable living spaces, making them ideal for families or groups seeking a memorable getaway. The proximity to the lively option of Key West, with its shops, restaurants, and beautiful beaches, enhances the appeal of renting a holiday home in Truman Annex.
Are there any Truman Annex holiday rentals with parking?
Vrbo offers a wide selection of holiday 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.
Can I book pet-friendly holiday rentals in Truman Annex?
In Truman Annex, there are several pet-friendly holiday rentals available, providing an excellent option for those wishing to travel with their furry companions. This charming area, located in Key West, offers a unique blend of historic architecture and vibrant setting. Many rentals come equipped with modern amenities such as full kitchens, private patios, and access to communal pools, ensuring a comfortable stay for both humans and pets alike.The location itself is ideal for pet owners, as it is within walking distance to several parks and green spaces. Nearby, the picturesque Fort Zachary Taylor State Park is a popular spot, featuring sandy beaches and shaded picnic areas where pets are welcome, making it a superb destination for leisurely afternoons outdoors. Additionally, the lively streets of Key West offer pet-friendly cafes and shops, ideal for those travelling with pets.
Can I find long-stay holiday rentals in Truman Annex?
A long-stay holiday 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 holiday rental?
The best time to visit Truman Annex for a holiday rental is during the peak season from January to March, with March being particularly popular. This vibrant period attracts visitors seeking a warm escape, as the temperatures in Truman Annex typically range from 20 to 28 degrees Celsius. With the pleasant weather, it's an ideal time for outdoor activities such as cycling through the historic streets or lounging on the nearby beaches.During these months, the area buzzes with energy, and you'll find plenty of opportunities to explore the rich cultural heritage, enjoy water sports, or dine at local eateries offering fresh seafood. The lively option is complemented by numerous festivals and events that showcase the unique charm of Key West.If you're looking for a more budget-friendly experience, consider planning your visit in October. This month often sees fewer tourists, allowing you to enjoy the tranquillity of Truman Annex while still relishing the area's natural beauty. October's warm temperatures are superb for outdoor exploration, and you can enjoy a more intimate experience with the local wildlife and scenery.
Are there any remote work holiday rentals in Truman Annex?
In Truman Annex, Florida, there are 24 remote work-friendly holiday rentals available, making it an excellent choice for those looking to blend work with leisure. This vibrant area is known for its historical charm and proximity to attractions such as the Ernest Hemingway Home and Museum and the lively Duval Street. Many rentals in Truman Annex come equipped with essential amenities for remote work, including high-speed internet, Wi-Fi in both rooms and public areas, and designated laptop workspaces.Travellers can expect comfortable living spaces that often feature modern furnishings, fully equipped kitchens, and outdoor areas for relaxation. The neighbourhood's picturesque streets and tropical setting provide an inspiring backdrop for productivity, while also offering easy access to local cafes and restaurants, great for a work break or after-hours enjoyment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Truman Annex holiday rental?
Book your Truman Annex holiday 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 holiday 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 unique blend of attractions that showcase the area's rich history and vibrant culture. The neighbourhood itself is a historic district, known for its charming architecture and proximity to popular sites. One of the main attractions is the Ernest Hemingway Home and Museum, where the famous author lived and wrote for nearly a decade, offering guided tours of the beautiful property and its lush gardens.Just a short stroll away, the lively Duval Street buzzes with shops, restaurants, and bars, providing a great atmosphere for dining and nightlife. Additionally, the nearby Fort Zachary Taylor Historic State Park is ideal for outdoor enthusiasts, featuring picturesque beaches, shaded picnic areas, and trails for walking or biking.The Truman Annex is also conveniently located near the Southernmost Point Buoy, a popular photo spot and a symbol of Key West's southernmost point in the continental United States.
Can I change or cancel my Truman Annex home rental booking on Vrbo?
To find Truman Annex holiday 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 holiday 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, 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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