Photo by Rick Tuers

Truman Annex holiday rentals

We found 1,249 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Truman Annex by choosing from 102 houses, 151 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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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.
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.
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.
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 Stayz.
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.
Are all fees included in the Truman Annex holiday homes prices shown on Stayz?
Stayz 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.
Are there any Truman Annex holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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 any discounts for Truman Annex holiday homes?
You can find great discounts on holiday homes in Truman Annex on Stayz, 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.
Can I change or cancel my Truman Annex holiday home booking on Stayz?
To find Truman Annex holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Truman Annex?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Truman Annex holiday home?
Book your Truman Annex holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Truman Annex?
Prices for holiday homes 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. Stayz offers something for every taste and budget, from affordable homes in Truman Annex to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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