Truman Annex holiday lettings

We found 1,339 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Truman Annex by choosing from 141 houses, 161 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:3 Oct - 10 Oct
  • 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, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

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.

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.

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

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.

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 accommodation in Truman Annex?
Condos are the most popular type of holiday rental in Truman Annex, according to our data. Even if you've got something else in mind, Vrbo 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 rental 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 Vrbo holiday rentals 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 Vrbo. Can't live without a hot tub? Use our filters to pick the features and amenities you need.
Are there pet-friendly holiday rentals 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 rentals on Vrbo. 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 Vrbo, and then spend your days splashing and playing in a swimming pool that's all your own.
What are popular rental amenities in Truman Annex?
A garden, a swimming pool and a nearby waterfront rank as the most popular rental amenities in Truman Annex. Whether you're taking to the road on your own, with your significant other or a group of best friends, Vrbo can help you find a holiday home that fits your style with all the features you're looking for.
Are there large group holiday rentals 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 rentals in Truman Annex that welcome kids?
Truman Annex has 285 family-friendly holiday rentals. And discovering a stay that welcomes kiddos is easy with Vrbo'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 rentals 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 rentals in Truman Annex?
Take off with your besties and enjoy total privacy and comfort in one of the 210 two-bedroom holiday rentals Truman Annex has to offer.
Are there holiday rentals with WiFi in Truman Annex?
Truman Annex has 113 holiday rentals 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 Vrbo homes make it a cinch to go online.
How can I find holiday rentals with air conditioning in Truman Annex?
Work out your travel dates and then use the filters to view holiday rentals with air conditioning in Truman Annex on Vrbo. 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 rental in Truman Annex?
We advise checking with the Truman Annex holiday home you'd like on Vrbo as the minimum age differs. However, normally it's 16, 18 or 21.
How long can I rent a holiday rental 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 Vrbo. 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.

More Holiday Rentals ideas

People also search for