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Explore Similar Homes Within 2 Miles of Truman Annex, FL

  • /6

    $1,000 per month

    • 1 Bed
    • 367 Sq Ft
    • Property for Rent

    600 Whitehead St Unit C-4, Key West, FL 33040

    Commercial office space in Old Town available for immediate use. Office is offered non-furnished, internet not included.

    Agent Photo

    Everett Watkins

    Keller Williams Key West Compass Realty

    (866) 823-0723

    600 Whitehead St Unit C-4, Key West, FL 33040
  • /5

    $2,500 per month

    • 2,244 Sq Ft
    • Property for Rent

    2001 Flagler Ave, Key West, FL 33040

    Prime 2,244 SQFT Vacant Lot Available for Rent.A rare opportunity to lease a centrally located vacant lot in the heart of New Town! Whether you're looking to advertise your business, operate a food truck, start a new venture, or create a space uniquely your own--this versatile lot offers endless potential. Multiple possible uses (tenant to verify).Please do not walk the property without prior

    Agent Photo

    Everett Watkins

    Keller Williams Key West Compass Realty

    (786) 244-5194

    2001 Flagler Ave, Key West, FL 33040
  • /14

    Call for Price

    Lofts at Bahama Village

    1 - 2 Beds

    750 Fort St, Key West, FL 33040

    750 Fort St, Key West, FL 33040
  • /13

    $3,800 per month

    • 2 Beds
    • 1 Bath
    • 912 Sq Ft
    • Property for Rent

    2401 Patterson Ave Unit 102, Key West, FL 33040

    Spacious 2BD/1BA - Renovated Second-Floor Duplex in MidtownBe the first to enjoy this beautifully renovated 2-bedroom, 1-bath upstairs apartment in the heart of Key West's desirable Midtown neighborhood. This bright and airy home features a large open-concept living room and kitchen, complete with brand-new stainless steel appliances, modern finishes, and sleek countertops. Enjoy the convenience

    Jody Clark Key West Luxury Real Estate Inc (KW)

    2401 Patterson Ave Unit 102, Key West, FL 33040
  • /12

    $5,000 per month

    • 2 Beds
    • 1 Bath
    • 1,008 Sq Ft
    • Condo for Rent

    1022 Fleming St Unit Lower, Key West, FL 33040

    Property Id: 1249660Fully Furnished, amazing 2 bedroom, 1 bathroom (upper level) newly furnished, gorgeous home in Key West on spectacular Fleming street in the old town, historic district, just a few blocks from famous Duval street. Amenities included: central air, central heat, deck, dishwasher, hardwood floors, stainless steel appliances, washer and dryer and pool. Small dog or two

    1022 Fleming St Unit Lower, Key West, FL 33040
  • /18

    $5,000 per month

    • 3 Beds
    • 2 Baths
    • 912 Sq Ft
    • Property for Rent

    2401 Patterson Ave Unit 101, Key West, FL 33040

    Spacious 3BD/2BA - Renovated First-Floor Duplex in MidtownThis fully renovated 3-bedroom, 2-bath apartment offers everything you need for comfortable long-term living in Key West's Midtown neighborhood. Located on the first floor of a freshly updated duplex, this home features a large open-concept living area and kitchen with all new appliances and high-end finishes. The unit includes a brand-new

    Jody Clark Key West Luxury Real Estate Inc (KW)

    2401 Patterson Ave Unit 101, Key West, FL 33040
  • /5

    $1,500 per month

    • 1 Bed
    • 1 Bath
    • House for Rent

    2102 Staples Ave, Key West, FL 33040

    Property Id: 1785777Key West, FL (Midtown) - available July 1Private furnished bedroom and bathroom with private entrance for rent for a single person. Room comes furnished including tv, microwave, refrigerator and window AC. Walking distance to the beach.  Ready to move in.$1500 per month - utilities and wi-fi included. 6-month lease. First month's rent ($1500),

    2102 Staples Ave, Key West, FL 33040
  • /14

    $4,800 per month

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Property for Rent

    844 Olivia St, Key West, FL 33040

    AVAILABLE SEPTEMBER 1,2025 3 bedroom 2 bathroom in Old Town Key West with off street parking. Make an appointment to view this home and see all the possibilities this home has to offer. First room can be a bedroom or living area. Back room is a washer dryer room, it also has a small bathroom and shower. Upstairs loft is a great room for a bedroom along with seating area or bedroom and office, one

    Rebecca Cobo Berkshire Hathaway HomeServices Knight & Gardner Realty

    844 Olivia St, Key West, FL 33040
  • /23

    $4,500 per month

    • 3 Beds
    • 2 Baths
    • 1,266 Sq Ft
    • Condo for Rent

    2408 Flagler Ave, Key West, FL 33040

    The spacious master suite features an en suite bathroom and direct access to the private backyard. One of the bedrooms makes an ideal office or guest room. The back patio was recently updated with elegant travertine pavers, and custom built-ins provide additional storage space, This charming 3-bedroom, 2-bath CBS home sits on a generous lot, complete with lush tropical landscaping and a stunning

    2408 Flagler Ave, Key West, FL 33040
  • /13

    $4,700 per month

    • 2 Beds
    • 1 Bath
    • 744 Sq Ft
    • Property for Rent

    1324 Seminary St Unit B, Key West, FL 33040

    This tastefully updated two-bedroom, one-bath condo in Midtown Key West is available for a yearly rental! Offering a cozy and inviting living space this property features a private pool, spacious outdoor living areas, and beautiful professional landscaping. Enjoy the convenience of two assigned parking spaces, plus additional room for scooters -- a rare find in this area. Ideally located less

    Rebecca Cobo Berkshire Hathaway HomeServices Knight & Gardner Realty

    1324 Seminary St Unit B, Key West, FL 33040
  • /9

    $5,500 per month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Condo for Rent

    1800 Atlantic Blvd Unit 302A, Key West, FL 33040

    1800 Atlantic blvd. Has so much to offer, quiet location, fantastic apartment views, and a long list of amenities.

    1800 Atlantic Blvd Unit 302A, Key West, FL 33040
  • /12

    $5,000 per month

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • Property for Rent

    417 Southard St Unit B, Key West, FL 33040

    This 2-bedroom, 2-bathroom furnished apartment is conveniently located just steps away from Duval Street, Mile Marker 0, and within walking distance to the Southernmost Point, Fort Zachary Taylor Historic State Park. The apartment boasts Beautiful bathrooms with walk-in showers, spacious kitchens equipped with upgraded stainless steel appliances, a stunning waterfall kitchen counter with seating,

    Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

    417 Southard St Unit B, Key West, FL 33040
  • /25

    $4,700 per month

    • 2 Beds
    • 1 Bath
    • 744 Sq Ft
    • Condo for Rent

    1324 Seminary St Unit 1324 Seminary St, Key West, FL 33040

    This tastefully updated two-bedroom, one-bath condo in Midtown Key West is available for a yearly rental! Offering a cozy and inviting living space this property features a private pool, spacious outdoor living areas, and beautiful professional landscaping. Enjoy the convenience of two assigned parking spaces, plus additional room for scooters — a rare find in this area. Ideally located less than

    1324 Seminary St Unit 1324 Seminary St, Key West, FL 33040
  • /8

    $7,000 per month

    • 4 Beds
    • 2 Baths
    • Property for Rent

    417 Southard St Unit A, Key West, FL 33040

    Long term rental, 4 bedroom, 2-bathroom furnished apartment is conveniently located just steps away from Duval Street, Mile Marker 0, and within walking distance to the Southernmost Point, Fort Zachary Taylor Historic State Park. The apartment boasts Beautiful bathrooms with walk-in showers, spacious kitchens equipped with upgraded stainless steel appliances, a stunning waterfall kitchen counter

    Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

    417 Southard St Unit A, Key West, FL 33040
  • /15

    $2,800 per month

    • 2 Beds
    • 1 Bath
    • 560 Sq Ft
    • Condo for Rent

    1209 William St Unit 1, Key West, FL 33040

    This 2/1 Old Town apartment is in good condition with a new shower and combination window and ductless a/c units. Stack laundry in the unit and 1 off street parking spot included. Available August 1st. F/L/S to move in. Please contact David Austin, Anchor Line Realty, Licensed Real Estate Broker for showings.

    1209 William St Unit 1, Key West, FL 33040
  • /14

    $3,450 per month

    • 1 Bed
    • 1 Bath
    • 450 Sq Ft
    • Property for Rent

    623 Whitehead St, Key West, FL 33040

    Charming 1-Bedroom Home in Old Town with Bonus Loft Space! Fully renovated 1-bedroom, 1-bathroom rental home in the heart of Old Key West, featuring a bonus loft, one off-street parking space and a washer/dryer inside. Fully furnished, the property includes a cozy sitting room, a well-equipped kitchen, large bedroom, and updated bathroom with new shower. Relax on the porch, surrounded by lush

    Damian Vantriglia Berkshire Hathaway HomeServices Knight & Gardner Realty

    623 Whitehead St, Key West, FL 33040
  • /6

    $2,200 per month

    • Studio
    • 1 Bath
    • 252 Sq Ft
    • Condo for Rent

    908 Elizabeth St Unit 4, Key West, FL 33040

    Very cute little garden studio available Early August. Small but in the very HEART of it all! Walk to everything Old Town has to offer! Tenant pays electric and cable/internet. F/S/S. Sorry No Pets!

    908 Elizabeth St Unit 4, Key West, FL 33040
  • /20

    $2,900 per month

    • 2 Beds
    • 1 Bath
    • 859 Sq Ft
    • Property for Rent

    2523 Seidenberg Ave, Key West, FL 33040

    SEASONAL RENTAL ONLY*Available Sept 15th-January 1stNestled in a private, fenced-in yard, this thoughtfully designed 2-bedroom 1-bath home offers modern comforts with timeless charm.Features Include:Dipping Pool: Refresh and unwind in your private pool.Spacious Porch: Enjoy morning coffee or evening cocktails in the breezy outdoor space.Dedicated Workspace: A stylish desk area for work or

    Jessica Celli Berkshire Hathaway HomeServices Knight & Gardner Realty

    2523 Seidenberg Ave, Key West, FL 33040
  • /28

    $3,300 per month

    • 2 Beds
    • 1 Bath
    • 700 Sq Ft
    • Condo for Rent

    1504 Flagler Ave, Key West, FL 33040

    We are family oriented here at this property, we make our tenants feel at home like family.

    1504 Flagler Ave, Key West, FL 33040
  • /34

    $3,600 per month

    • 1 Bed
    • 1 Bath
    • 416 Sq Ft
    • House for Rent

    709 Emma St Unit 1, Key West, FL 33040

    Tropical and Islandy Bungalow Style Home In KEY WEST!! Cute As A Button! 1 Bedroom 1 Full Bath, Furnished, Very Modern, Remodeled, Single Family Home. Located In Old Town/Downtown Area. 3 Blocks From Duval St., Yet Far Enough Away To Enjoy Your Private, Quiet Lifestyle. Property Is Fenced. Large Front Porch, Spacious Side Yard For Entertaining. Assigned Off Street Parking. Central Air. Electric,

    Sabrina Liguori Premium Properties Real Estate

    709 Emma St Unit 1, Key West, FL 33040
  • /28

    $3,000 per month

    • 2 Beds
    • 1 Bath
    • 700 Sq Ft
    • Condo for Rent

    1504 Flagler Ave, Key West, FL 33040

    We are family oriented here at this property, we make our tenants feel at home like family.

    1504 Flagler Ave, Key West, FL 33040
  • /16

    $5,500 per month

    • 2 Beds
    • 2 Baths
    • 1,357 Sq Ft
    • Condo for Rent

    1800 Atlantic Blvd Unit 122C, Key West, FL 33040

    This tastefully decorated 2 bedroom 2 bath is being offered furnished annually but will consider seasonal occupancy with 6 months or longer. Some of the building amenities include the Oceanfront heated pool, hot tub, BBQ areas, Gym, tennis courts and assigned covered parking with guest parking. The building has controlled access and is conveniently located next to Smathers Beach.

    Kenneth Herzbrun Lokation Real Estate

    1800 Atlantic Blvd Unit 122C, Key West, FL 33040
  • /58

    $12,500 per month

    • 3 Beds
    • 4 Baths
    • 2,800 Sq Ft
    • Property for Rent

    400 Aronovitz Ln, Key West, FL 33040

    Zen Villa - A Luxe Retreat in the Heart of Old Key West! A tranquil reprieve amidst the city's energy, waiting to welcome you in. Just steps from the vibrant heartbeat of Old Town, Zen Villa is where modern luxury meets island tranquility. Designed for those who crave both exhilaration and escape, this stunning contemporary retreat offers an effortless blend of indoor-outdoor living, lush

    Damian Vantriglia Berkshire Hathaway HomeServices Knight & Gardner Realty

    400 Aronovitz Ln, Key West, FL 33040
  • /37

    $13,000 per month

    • 4 Beds
    • 4 Baths
    • Property for Rent

    2214 Seidenberg Ave, Key West, FL 33040

    Welcome to your luxurious oasis in Key West, where modern comfort meets tropical paradise. This stunning new construction home features four spacious bedrooms, each with an en suite bathroom. Lushly landscaped grounds, this 5,700 square foot property offers plenty of room to unwind and enjoy the beauty of the island.Imagine starting your day with a refreshing swim in the large, private, heated

    Paige Bethel Island Home Realty Inc.

    2214 Seidenberg Ave, Key West, FL 33040
  • /33

    $14,000 per month

    • 4 Beds
    • 4.5 Baths
    • 2,250 Sq Ft
    • House for Rent

    710 Caroline St, Key West, FL 33040

    This magnificent, historic, turn-key home is located on infamous Caroline Street, just a few blocks from Duval Street in the Historic Seaport area, making it one of the most ideal locations in Key West. The property underwent a multi-year complete renovation culminating in 2023, including being raised appx. 5 feet and impact glass windows & doors. The 2,250-square-foot home features a stunning

    jesse friedman Real Broker, LLC

    710 Caroline St, Key West, FL 33040

Why Live in Truman Annex

Truman Annex in Key West offers a diverse range of housing options, from classic Southern Cottage-style row homes to grand Italian Revival residences, all unified by their white exteriors. The neighborhood includes multi-unit properties like The Foundry’s townhouses and Harbour Place condos, which repurposed former military buildings. Amenities such as a large community pool at Shipyard Condos and private courtyards at President’s Walk townhouses enhance the living experience. Many properties allow for weekly and monthly rentals, appealing to seasonal residents. The area is safer than the national average, providing a secure environment for families and individuals alike. Truman Annex is within walking distance of Duval Street, known for its vibrant bars, restaurants, and shops. Popular spots include Hog’s Breath Saloon, Sloppy Joe’s, and the Green Parrot, which hosts live music regularly. Dining options extend beyond Duval Street with establishments like Blue Heaven and El Meson de Pepe. For groceries, Fausto’s Food Palace and national chains like Publix and Winn-Dixie are about 3 miles away in New Town. Cultural attractions near Truman Annex include the Custom House Museum, the Waterfront Playhouse, and the Key West Aquarium. The neighborhood also hosts various events throughout the year, such as Hemingway Days and the Key West Songwriters Festival. Educational options are strong, with highly rated schools like Sigsbee Charter School and Key West High School serving the area. Truman Waterfront Park and Fort Zachary Taylor Historic State Park offer recreational opportunities, including playgrounds, trails, and popular beaches for swimming and snorkeling.

Frequently Asked Questions

What are the most popular neighborhoods for renters near Truman Annex?
The most popular neighborhoods for renters near Truman Annex are Old Town, Mid Town and New Town.
What are the most popular zip codes for renters near Truman Annex?
The most popular zip codes for renters near Truman Annex is 33040.
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