Truman Annex holiday lettings

We found 1,306 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Truman Annex by choosing from 139 houses, 152 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.

Holiday rentals with weekly discounts - Truman Annex

Showing deals for:23 Jan - 30 Jan

Image gallery for Heated Pool, Steps to Duval St - Poolside Paradise

Private Heated Pool with Outdoor Dining
9.2 out of 10, Wonderful, (17 reviews)
Wonderful
(17 reviews)

Heated Pool, Steps to Duval St - Poolside Paradise

Key West, FL

8% off
Price is £9,049
for 7 nights, 1 home
£1,293 per night
includes taxes & fees
Heated Pool, Steps to Duval St - Poolside Paradise

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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 a popular choice among holiday rentals, with several available throughout the area. These condos typically feature modern amenities such as fully equipped kitchens, spacious living areas, and access to communal pools, making them ideal for travellers seeking comfort and convenience. Additionally, apartments and holiday houses are also common, providing diverse options for visitors. Most holiday houses offer more space and privacy, often including private gardens and outdoor seating, great for families or larger groups.
Are there any beach house rentals in Truman Annex?
In Truman Annex, Florida, several beach house rentals are available, primarily located in this charming, gated community close to the vibrant heart of Key West. These properties typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and inviting living areas, making them ideal for families or groups. Many rentals also come with private outdoor spaces, such as patios or balconies, where guests can unwind and enjoy the tropical surroundings.
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 conveniently. Many properties feature heated pools for a comfortable swimming experience, along with shared pool access, providing a social atmosphere for relaxation. Additionally, a patio area is commonly available, superb for enjoying the warm Florida evenings.
Are there any family house rentals in Truman Annex?
In Truman Annex, a charming neighbourhood in Key West, there are several family-friendly house rentals available. This area is known for its picturesque streets and proximity to various attractions, making it an excellent choice for families. Many of the properties feature spacious living areas, fully equipped kitchens, and outdoor spaces where children can play or families can enjoy al fresco dining.
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 Key West, offers a unique blend of history and tropical beauty. Travellers can expect amenities such as private pools, relaxing hot tubs, and outdoor areas superb for enjoying the sunny weather. Many properties also include fully equipped kitchens, spacious living areas, and access to nearby attractions, making them ideal for families or groups looking for a comfortable getaway.
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.
Are there pet-friendly holiday rentals in Truman Annex?
In Truman Annex, travellers will find several pet-friendly holiday rentals that cater to those looking to enjoy a stay with their furry companions. This charming neighbourhood, located adjacent to the vibrant heart of Key West, offers a mix of accommodation options, including quaint cottages and modern townhouses. Many of these rentals come equipped with amenities such as fully furnished kitchens, outdoor spaces ideal for relaxation, and sometimes even private pools, making them superb for families or groups.
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?
March is the most popular month to visit Truman Annex, as it falls within the peak season that runs from January to March. During this time, travellers flock to the area to enjoy the sunny, warm weather, with temperatures typically ranging from the mid to high 20s Celsius. This climate is superb for outdoor activities like beach lounging, water sports, and exploring the vibrant local scene.

The peak season in Truman Annex is characterised by a lively atmosphere, with plenty of opportunities for sightseeing and socialising. Visitors can explore the stunning beaches, historic sites, and the famous nightlife of nearby Key West, all while soaking in the beautiful coastal views.

For those considering budget-friendly options, October offers a quieter experience with lower rental rates. The weather is still pleasant, making it a lovely time for leisurely walks and peaceful beach days without the hustle and bustle of peak season.
Are there any remote work holiday rentals in Truman Annex?
In Truman Annex, Florida, there are several remote work holiday rentals available, making it an excellent choice for those who need to balance work and leisure. The area offers a variety of properties equipped with essential amenities like Wi-Fi, dedicated workspaces, and safety features to ensure a comfortable and productive environment. Many rentals also provide access to business centres, which may be inclusive of resort fees, allowing for a seamless work experience. 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?
In Truman Annex, visitors can immerse themselves in the vibrant atmosphere of Key West. The neighbourhood is renowned for its charming, historic homes and proximity to popular attractions such as the Ernest Hemingway Home and Museum, where the famed author lived and wrote. Just a short stroll away, you can explore the lively Duval Street, lined with shops, bars, and restaurants, offering a taste of local culture and cuisine.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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