Truman Annex holiday lettings

We found 1,313 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Truman Annex by choosing from 113 houses, 157 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.

Find spaces that suit your style

Why visit Truman Annex

  • Rich historical charm: Truman Annex is steeped in history, featuring historic houses and vibrant streets that reflect Key West's unique heritage.
  • Beautiful beaches: Enjoy the inviting beaches nearby, perfect for relaxation and sunbathing.
  • Water sports galore: Engage in a variety of water sports, from snorkelling to sailing, offering adventure for all ages.
  • Community atmosphere: Experience the close-knit community feel, making it a welcoming destination for families and travellers alike.
  • Varied accommodation options: Choose from private homes, stylish condos, and charming cottages to suit your holiday needs.

Popular types of accommodation around Truman Annex

At Vrbo, we offer a delightful selection of vacation rentals in Truman Annex, including private homes, stylish condos, and charming cottages. Whether you're seeking a spacious retreat for the family or a cosy getaway for two, our Truman Annex rentals cater to all preferences. Explore the unique charm of Key West while enjoying the comfort and convenience of your own holiday home. Discover your perfect Truman Annex vacation rental today!

  • Houses: The top choice for those visiting Truman Annex, offering spacious and comfortable living perfect for families or groups.
  • Condos: A popular option for tourists, providing modern amenities and a sense of community in a vibrant setting.
  • Cottages: These quaint and charming abodes offer a cosy atmosphere, ideal for a romantic getaway or a peaceful retreat.
  • Apartments: A practical choice for those seeking a self-catering experience with easy access to local attractions.
  • Villas: Luxurious and spacious, these accommodations provide an upscale stay with private amenities.**

Top attractions near Truman Annex

Truman Annex is an ideal destination for family holidays, business trips, or city-themed escapes. Immerse yourself in the area's rich culture by exploring historic houses, vibrant streets, and modern squares. Whether you're seeking adventure or a cultural experience, Truman Annex offers a variety of attractions, including the opulent surroundings of the annex itself. Don't miss out on these captivating points of interest during your visit to Key West.

  • Duval Street: A vibrant thoroughfare teeming with lively bars, eclectic shops, and delightful eateries, perfect for soaking up the local atmosphere and nightlife.
  • Mallory Square: A bustling modern square renowned for its stunning sunset celebrations, featuring street performers, artisan vendors, and breathtaking views of the Gulf of Mexico.
  • Ernest Hemingway Home and Museum: A charming historic house that once belonged to the famed author, offering a glimpse into his life and works, surrounded by lush gardens and unique polydactyl cats.

Things to do recommended for couples

For a romantic getaway in Truman Annex, indulge in a sunset sail on a catamaran, explore the charming streets by bicycle, or enjoy a candlelit dinner at a waterfront restaurant. Don't forget to take a leisurely stroll along the beach as the sun dips below the horizon.

Things to do recommended for families

Families visiting Truman Annex can enjoy a refreshing day at the MLK Community Pool & Community Center, located 435m away. This outdoor pool offers a vibrant atmosphere perfect for sports and family fun, ensuring a memorable experience for all ages.

Things to do recommended for groups

Groups visiting Truman Annex can enjoy a round of golf at the nearby Key West Golf Club, immerse themselves in a captivating performance at the Waterfront Playhouse, or browse unique items at The Kite House, all within easy reach for an unforgettable local experience.

What do I need to keep in mind when booking a vacation around Truman Annex

When you are planning a trip, whether it's with friends, family, or your pets, or if you're seeking extended stays, it’s essential to apply the right filters to meet your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Truman Annex with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options, and many more, on Vrbo.
  • Traveling to Truman Annex with young kids: Travelling with young children can be quite demanding. It’s important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it would be wise to take into account how close you are to family-friendly attractions.
  • Taking your pets with you to Truman Annex: For many, a family holiday feels incomplete without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Most 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 in search of holiday rentals offering discounts for stays of a month or more, you've come to the right place. By using the appropriate filter, 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 in Key West, Florida, offers a delightful blend of tropical charm and historical intrigue, making it an ideal destination for families and adventurers alike. This vibrant neighbourhood boasts picturesque streets, inviting beaches, and a close-knit community atmosphere. Just a stone's throw away, you can explore the rich history of Key West, indulge in water sports, or simply unwind in a beach getaway. For your next holiday, Truman Annex promises an unforgettable experience.

  • Key West: Key West is a vibrant city located a mere 186m from Truman Annex, embraced by the sparkling waters of the Gulf of Mexico. This island paradise is a popular destination for families and business travellers alike, offering a delightful blend of city-themed experiences. Visitors can explore a variety of shopping areas and malls, while the nearby beaches provide an inviting spot for relaxation. Don't miss the lively streets that showcase the island's unique charm, making it a perfect place to unwind or engage in exciting activities.
  • Old Town Key West: Situated 435m from Truman Annex, Old Town Key West is a picturesque neighbourhood that embodies the essence of Key West's rich history and culture. This area attracts families and city explorers with its charming streets and local shops. You'll find a wonderful array of shopping venues and resorts, all within walking distance. The proximity to beautiful family-friendly beaches allows for leisurely days soaking up the sun, while the vibrant atmosphere makes it an ideal spot for family outings and leisurely strolls.
  • Key West Historic District: Located just 373m from Truman Annex, the Key West Historic District is a treasure trove for those seeking a glimpse into the island's storied past. This neighbourhood is perfect for families and business visitors who appreciate historical architecture and unique local shops. With an abundance of shopping areas and resorts, it offers plenty of attractions. The inviting streets and nearby beaches enhance the experience, making it a must-visit for anyone keen to explore the charm and history 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.

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 simple

Are you hoping to reduce costs on your upcoming trip? One effective approach is to maintain flexibility with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo accommodation that suits your budget, feel free to utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers a handy platform for you to plan new trips, resume your previous arrangements, or manage your travel itinerary with ease. You can view the properties you've saved or booked, neatly organised into categories such as Potential, Upcoming, and Current Trips. To get started with Trip Boards, simply 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.

More holiday ideas