Hotels in Truman Annex

Truman Annex offers a variety of hotel accommodations perfect for couples seeking a romantic getaway. You'll find charming historic hideaways, cozy condos, and spacious hotel suites that provide a comfortable stay. Many options feature private pools and stunning waterfront views, allowing you to relax in style. Whether you prefer a secluded retreat or a vibrant atmosphere, this picturesque area has something for everyone, ensuring a memorable vacation in beautiful Key West. Here are some of our travelers' favorite hotels in Truman Annex:

• L'Habitation Guest HouseOpens in a new window: This cozy 2.5-star guesthouse is conveniently located within a mile from Truman Annex, making it an ideal choice for adventure-seeking travelers. Guests can enjoy a variety of exciting activities nearby, such as snorkeling, skydiving, and boat tours. The property is well-suited for those looking for an adventurous vacation experience, offering recreation options onsite or within close proximity.
• Weatherstation InnOpens in a new window: Situated just a mile from Truman Annex, this charming 2.5-star bed and breakfast caters to travelers who appreciate boutique experiences. With unique decor and artworks, guests will feel a distinct ambiance during their stay. The hotel provides numerous adventure activities nearby, including kayaking, parasailing, and bicycle rentals, ensuring a memorable getaway filled with exploration and fun.
• The Saint Hotel Key West, Autograph CollectionOpens in a new window: A 3.5-star hotel located within a mile from Truman Annex, this property balances adventure and business amenities. It's perfect for travelers who require business services while also wanting to enjoy recreational activities like sailing and windsurfing nearby. With a focus on providing a comfortable stay and essential facilities for business guests, this hotel is an excellent choice for both leisure and work-related travel.

A visit to Truman Annex offers a perfect beach getaway with pristine shores, scenic parks, and inviting picnic areas. Spend three days enjoying outdoor adventures like boating, hiking along picturesque trails, and relaxing on the beach, while also exploring vibrant shopping areas and recreational spots for a well-rounded experience. Here's a quick itinerary to make the most of your trip to Truman Annex:

• Day 1: Start your Key West adventure on the vibrant Duval Street, lined with lively bars, unique shops, and restaurants. After soaking in the atmosphere, make your way to the Observation Tower for stunning panoramic views of the island and its surroundings. Conclude your day with a relaxing sunset sail aboard the Schooner Western Union, where you can enjoy the breathtaking colors of the sky as the sun dips below the horizon.
• Day 2: Begin your day at Mallory Square, a hub of activity where you can enjoy street performers and local vendors. From there, stroll over to the Key West Historic Seaport, where the charm of the waterfront and the boats will captivate you. Don’t miss St. Paul's Episcopal Church, known for its beautiful architecture and serene atmosphere—a perfect spot to reflect on your day.
• Day 3: Start with a visit to the Southernmost Point buoy, a must-see landmark for a classic photo op. Next, head over to Smathers Beach for some relaxation; enjoy the sun, sand, and surf. Finally, delve into literary history at the Ernest Hemingway Home and Museum, where you can explore the life and works of this iconic author while wandering through the beautiful gardens.

1. Book for the cheapest times: The most affordable time to visit Truman Annex is from July to September, when hotel rates are significantly lower. If you're traveling internationally, aim to book your flight at least four months in advance to secure better prices. For a budget-friendly trip, a stay of at least 3-4 days is ideal for experiencing the key attractions, which include the beach, a history museum, and family-friendly areas. This way, you can enjoy great value for your money while exploring the charm of Truman Annex.
2. Look for last-minute deals on Hotels.com: If you're seeking great last-minute deals to Truman Annex, exploring the DealsOpens in a new window or Last-Minute DealsOpens in a new window sections on Hotels.com can be a smart move. You could find discounted hotel rates as your travel date approaches. Additionally, consider signing up for email alerts or push notifications from Hotels.com to stay informed about flash sales and special promotions. This way, you're more likely to uncover flexible booking options and compare prices, ensuring you take advantage of any savings available.
3. Be flexible with dates: Hotel prices can fluctuate due to factors like the location, star rating, and the time of year. Therefore, being flexible with your travel dates may help you save on hotel expenses in Truman Annex.
4. Consider your location: When booking on Hotels.com for your vacation, it's important to think about your location. Staying near major attractions or downtown areas can offer convenience, but it usually tends to come with a higher price tag. For more affordable options, consider looking for hotels in less central neighborhoods, while still balancing cost with the accessibility of the sites you want to visit.
5. Upgrade with One Key: Book your next stay in Truman Annex and join Hotels.com’s One Key programme which allows members to earn and redeem rewards points for hotel bookings. Move through blue, silver, gold and platinum tiers and unlock benefits such as earning free nights, room upgrades, special discounts, and exclusive deals for members. Sign up now.

Truman Annex experiences its lowest average temperature in January, at 71.1°F (21.7°C), while August is the hottest month, with an average temperature of 84.4°F (29.1°C). September is typically the wettest month. If you’re looking to soak up the lively atmosphere in Truman Annex, March, June, and July are the peak months to visit, bustling with fellow travelers. During this peak period, the weather is mostly sunny, accompanied by dry to light rainfall. However, if you prefer a more relaxed experience, September to November are perfect for a quieter getaway, marked by light rainfall and mostly sunny conditions.