Known for the location of the Winter White House, dedicated for President Truman, Truman Annex is a peaceful neighborhood as well as a military installation in the state of Florida. Situated in forty-five acres of land in the center of Key West’s celebrated district, this area is of significance to the history of the naval force of the US. Truman Annex has had undergone wholistic redevelopment since 1996 and at present time is home to national museums, family homes, high-end condominiums, hotels, retail shops, restaurants, and more. In case you have plans to visit this area of Key West, Florida, check out these wonderful Vrbo accommodations in Truman Annex, and choose from the list we have narrowed down for you.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on March 13, 2023.
1. Lovely unit with a shared pool (from USD 319)
Spend your vacation days in one of the units of Shipyard Condominiums. Only two blocks from Duval Street and the major Old Town Key West attractions, the property never runs out of nearby things to do when you’re exploring the district. Even the beach is within walking distance, so get your swimwear ready.
The unit has a cozy living room with comfy seating and large flat-screen TV so you can watch a blockbuster film in style. The private bedroom is equally comfortable with its snug bed and own flat-screen TV. Do you prefer homecooked meals on most days of your vacation? The galley-type kitchen is sure to be a dependable corner for that as it is equipped with essentials. Your booking also provides you access to a shared pool and an off-street parking space.
Top guest reviews
Cleanliness:
unit could use a deep cleannice apartment clean unit quietthe unit itself was very clean well furnished and very quietthe apartment was clean and furnished with everything we neededthe condo was perfect---clean comfortable stylish and has everything you needHost:
rating details: the property manager was more than helpfulRead more reviewsLocation:
enjoyed the location and ability to walk everywherewe really enjoyed being close to everythinglovely condo in a perfect location with everything we needed plus beautiful wood cabinetrywe love the location to restaurants duval and our other favorite placesi was very happy with the location
2. Spacious vacation home along Admiral's Lane (from USD 370)
For those who want a spacious vacation home for up to four guests, this two-story home in the prestigious Admiral’s Lane neighborhood definitely fits the bill. The bright and breezy home features an open layout main floor showcasing a comfy living area, a six-seater dining table, and a well-equipped kitchen space. Free wifi and a cable TV are also included for an entertaining stay. Through the French doors, you’ll be greeted by a large private deck that offers plenty of space to unwind and enjoy a casual meal. The second level houses the two gorgeous bedrooms fitted with plush beds.
For some basking under the sun, you can enjoy the nearby community pool or walk to the pristine beach for a dose of sand and coast. When booking, note that the property has a seven-night minimum stay policy.
Top guest reviews
Cleanliness:
every part of the property was very clean and well keptthe vacation rental was very cleanthe home was clean and well keptHost:
rating details: the property manager was very helpfulrating details: the property manager was very helpfulrating details: the property manager was very helpfulrating details: the property manager was very helpfulrating details: the property manager was very helpfulRead more reviewsLocation:
great location and lovely propertybeautiful neighborhood and great locationproperty was perfect the location was greatthe location was perfect for walking to duval stthe location is perfect for walking and bike riding the pool is very close by and clean
3. Vibrant vacation home for four (from USD 350)
You’ll definitely want to explore the locality when you take refuge in this condo unit located two blocks from the hotspots in Old Town Key West and Duval Street. Take a day out and stroll around shops and museums then taste the local cuisine in the great restaurants. You can also embark on the nearby beach and soak up the sun.
Stepping into the place, you’ll be welcomed by a gorgeous deck perfect for hanging out or alfresco dining. Indoors, the vibrant living room looks cozy with its plush sofa and a flat-screen TV. Free wifi is on-hand to keep your devices efficient. It also highlights a well-equipped kitchen for your skillful cooking and two comfy bedrooms for recharging overnight. Those who plan to rent for at least 28 days can be allowed to stay with their pets.
Top guest reviews
Cleanliness:
the condo was clean and looks like the decor was recently updatedRead more reviewsLocation:
such a pretty area and so quiet despite being so close to everythinggreat location quiet clean with a nice pool
4. Cozy two-level retreat in the Southard Court area (from USD 329)
Have an easy-going getaway in Key West with a stay at this two-level home nestled in the Southard Court area of Truman Annex. Its first floor features an open concept interior comprising the living space with a large TV, a dining table for six, and an equipped kitchen for all your cooking sprees. The living room also extends to a back deck where you can do the outdoor grilling. Make your way to the two bedrooms tucked upstairs when capping the night off.
Staying here also means having to enjoy a shared pool right in front of the property. If you plan to arrive by car, you’ll get one parking space reserved for your vehicle. Be aware that you have to stay for at least seven days to be able to book the unit.
Top guest reviews
Cleanliness:
other than that the condo was clean comfortable and well stockednot to mention the character of the condo and how clean it wasHost:
the staff was wonderful; very helpful and friendlyrating details: the property manager was very helpfulrating details: the property manager was very helpfulrating details: the property manager was very helpfulrating details: the property manager was very helpfulRead more reviewsLocation:
i loved the location to duval and also the location to the poolperfect location for beach and town exploringloved being near fort zach state parkgreat location secure and quiet yet close to all the action on duval streetgreat location walkable to all things key west
5. Oceanfront penthouse with a patio (from USD 789)
Boasting of a wonderful uninterrupted view of the gulf and the docked cruise ship, featuring luxurious and elegant interior design and modern pieces of furniture and appliances, Gulfside Vistas is a stylish and relaxing place to stay in Truman Annex. This Vrbo accommodation rental houses two cozy bedrooms with spacious wardrobes and three lovely private bathrooms, ideal for six people. Aside from that, the lounge area is so relaxing that you would just want to lie all day. There is also a modern and fully equipped kitchen and a dining area in a mini bar type setting. A patio is right outside the penthouse where you can have quality time in and sip cocktails as you watch the beautiful sunset.
Top guest reviews
Amenities & Room:
The condo is in need of repairsThere are two bedrooms one with twin beds and each bedroom has its own bathroom (the one for the kids room is in the hall right outside the bedroom door)The concierge service was helpful SamThe kitchen was well stocked in dishes pansThere is also another powder room and a laundry roomCleanliness:
Pool clean and very quiet pool areaThe property was clean and well appointedI can't say enough about Key WestProperty was clean and close to walking distanc to attractions and main strip- Duval StreetHost:
He was also there to help with an easy departureHe was always quick to respond to texted messages regarding questions and needs while at the propertyhe met us upon arrival to greetrep met us at the property and was great Excellent recommendations for foodthe contact person is greatRead more reviewsLocation:
Last Key Realty provided SUPERIOR customer serviceTucked inside Truman Annex in a gated community sits this amazing vacation condoViews are magnificent from every room in the condo Close to Duval and Mallory Square for nightlife but peaceful and quiet within the complex Close to Fort Zachary for swimming every day in the...The property and location felt posh - not what we usually rent Shel from Last Key RealtyClose proximity to restaurants and attractions but the neighborhood (Truman Annex) is quiet
6. Fabulous stay in a gated community (from USD 501)
Situated in a prestigious gated community in Key West, nesting in the Foundry, this stylish Vrbo accommodation will make your Truman Annex vacation more lovely and delightful. Its location is ideal for tourists as it is proximate to the popular Duval Street, Mallory Square, and other city destinations. It can accommodate up to six guests, featuring two lovely bedrooms and three private bathrooms. The furnishing is very cool and airy which makes it more relaxing for the guests. It showcases a high ceiling that makes the place well lit and ventilated. Plus, the lounge area makes you feel at home. Also, included in this accommodation is a fully equipped kitchen and a spacious dining area.
Top guest reviews
Amenities & Room:
the bed in the master bedroom was a sleeper's bedplenty of towels pillows blankets beach towels and chairs and a well equipped kitchenI also wish there were overhead lights in the bedroomsHe likes it cold at nightThe only thing we missed was music by the poolCleanliness:
The washer and dryer was used often it eliminated over packingVery clean nice and close to everythingThe property was clean and well maintained Just about everything we needed was available for our use:Villa Bahama was well appointed clean and a beautiful town homeHost:
He was there to get us settled in and show us where everything was stored even gaveVery helpful friendly and quick to respond when we had any questions or concernsThey were super responsive to any issues and their Concierge ServiceThe concierge service helped us find the best day trips and were there for any and all questionsHe helped us with picking the best places to eat and visitRead more reviewsLocation:
Truman Annex was within walking/biking distance to everythingThe instant we walked into the propertyIt's in a quite community but a stone's throw away from Duval Street and the wharf areaIt really has the Key West feel There is a note on the thermostat to not set it below 70The property had everything we needed making it convenient for families that travel from afar
7. Charming Vrbo accommodation (from USD 326)
This charming fully furnished accommodation in Truman Annex is the perfect spot for tourists as it is close to the city’s landmarks, restaurants, cafes, retail shops, and other tourist destinations. Plus, going home to this Vrbo accommodation will always be exciting as it is relaxing and has a homey ambiance. It features a simple, chic, and modern interior design style and well-curated decors and furniture. It houses two lovely bedrooms and three charming private bathrooms. Plus, there is a cute little dining area with a fully equipped kitchen. Their rooms even have a patio where you can bask in the morning sunlight or have some quality time in drinking coffee. On top of that, it is within a short distance walk from the beaches and the state park.
Top guest reviews
Amenities & Room:
The townhouse was as depicted in the description and picturesThe only floor with window or door screens was the top floorThere is a problem with the air conditioningThe kitchen is somewhat under equipped and guest bedroom could use better lighting (as per the boys) Would stay at property again over all satisfiedThe outdoor furniture comprised of two small rusted chairs a rusted bistro table and two beatup Adirondack chairs that were very uncomfortableCleanliness:
The house was clean and well equippedIt was very clean and comfortableThe vacation rental was very cleanThe vacation rental was very cleanThe vacation rental was very cleanHost:
They responded quickly to fix and took care of usGreat booking experience and useful app added to make our stay very enjoyableI was very happy with the locationI was very happy with the locationI was very happy with the locationRead more reviewsLocation:
Great place in a great locationIt is in a lovely locationI recommend this vacation rental Reviewer Comments:Very quite area but within 10 minutes walk from main street with restaurants and barsIt was very tranquil but was walking distance to Mallory Square and Duval StreetA couple of blocks to Mallory Square a couple of blocks to our favorite bars on
8. Stylish townhouse with a pool (from USD 342)
Featuring a stylish, fully furnished home, this rental is like a home away. It exudes a relaxing ambiance, and it has amazing amenities that will make your stay worthwhile. It features two comfortable bedrooms, three bathrooms, a spacious and cozy lounge area, a fully equipped kitchen, a lovely dining area, and a patio. Aside from that, this location is perfect for tourists who like city tours and lovely walks as it is close to the popular landmarks in the area. This accommodation also has wifi access, a flat-screen television, and basic essentials are provided to guests.
Top guest reviews
Amenities & Room:
the first floor has a nice and comfortable living room area, featuring plenty of comfortable chairs and a large screen tvloved the bedrooms with their own bathroomsthe pool is small but adaquate for cooling off on hot daysthe condo was very spacious and had all the amenities we neededthere were also towels for use at the poolCleanliness:
the unit was very clean and extremely comfortableit was very clean and decorated so cuteclean, quiet and perfect for usvery cleanlocation is everything and the truman annex is the place to beHost:
they made sure we had information about the property and the surrounding area to feel at homewe have been going to key west for 18 years and have rented in the truman annex 13 timesvery easy checkin/checkout and randy was very responsive when we pointed out a very small problem that needed to be fixedwe rented truman annex foundry #14 and loved every minute of itno matter the time coming home we always felt safe within truman annexRead more reviewsLocation:
beach is also a quick bike ride awayclose enough to walk to everythinggreat house in a great locationi loved the location everything was within walking distanceonly a few minutes to mallory square or zachary taylor state park
9. Classic condo with a shared swimming pool (from USD 878)
Located within a short distance from the city’s top tourist destinations, this stylish condo unit is like a homey nest after a busy day touring the city. It is fully furnished, with fabulous interior design, has lovely amenities, and exudes a relaxing and peaceful ambiance. This Vrbo accommodation is ideal for four guests as it has two cozy bedrooms and three charming bathrooms. There is also a fully equipped kitchen with a dining area where guests can prepare their meals. Basic essentials are also provided to guests for added convenience.
Top guest reviews
Host:
but away from the hustle-and-bustle of Duval Street Very cute and well furnishedRead more reviewsLocation:
Great location walking distance to everythingMoved to this property due to Irma Loved the property and great locationWe loved it and the location was greatLoved the location and the decorWe had the best time in this lovely house Location is perfect you can walk everywhere
10. Spacious accommodation for four (from USD 475)
If you are looking for a place to stay in Truman Annex, this lovely townhouse can accommodate up to four guests. It is fully furnished, well equipped with fantastic amenities, and exudes a home away from home kind of ambiance. Including two cozy bedrooms, three private bathrooms, a comfy lounge, fully equipped kitchen, and dining space, coming home to this wonderful home after a busy day at the town center will always be a delight. Aside from that, it is located in one of the most prestigious neighborhoods in Truman Annex. The surrounding area of this accommodation is a tourist destination in itself, picture perfect, exquisitely landscaped, and has park-like features.
Top guest reviews
Amenities & Room:
the mattress is extremely comfortablewe loved the side courtyard and had breakfast there every morningCleanliness:
the house itself was very clean and well appointedtownhouse exactly as described & true to photographs; exceptionally clean & well stockedunit is nicely decorated and very cleanthe condo is clean and spacious with comfortable furnitureit's extremely spacious and cleanHost:
mike the owner is great to work withRead more reviewsLocation:
the location is perfectthe location was within easy walking distance to restaurants shopping groceries and points of interestsuperior location & very safe areagreat property with a great locationit's an easy walk to duval and all of our favorite spots
Hello Truman Annex
Visiting fantastic landmarks and tourist destination can take up most of your day’s energy as much as exploring local restaurants and bars and swimming in beautiful beaches. But if you have a beautiful place to stay, there is nothing to worry about. That is why we have prepared a list of the best Vrbo accommodations found in Truman Annex, Key West, Florida, to help you narrow down your choices and enjoy the whole vacation experience. Remember this list by heart and everything will surely be smooth sailing and hassle-free.
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