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Old Town Homes for Rent

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  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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 Old Town

Old Town in Key West is a historic neighborhood known for its distinctive conch-style homes, characterized by cozy front porches, wooden shutters, and intricate trim. Many of these homes, particularly in Bahama Village, date back to the 1800s and are built on raised platforms to improve air circulation and reduce mold and water damage. The area is in the X-flood zone, making it less flood-prone than other parts of Key West, though flood insurance and hurricane preparedness are recommended. Homeowners must maintain the original exterior of their properties, with renovations reviewed by the Historic Architectural Review Commission. Interiors, however, are often modernized with open floor plans and updated kitchens. The neighborhood is rich in cultural and culinary attractions, with numerous restaurants offering local specialties like conch fritters and Key lime pie. Notable dining spots include Old Town Tavern & Beer Garden, Blue Heaven, and Santiago’s Bodega. For things to do, residents can explore the Red Barn Theatre, Key West Theater, and Tropic Cinema, or visit the Key West Museum of Art & History. Fort Zachary Taylor Historic State Park and Truman Waterfront Park provide outdoor recreation options, including snorkeling, picnicking, and a weekly farmers market. Key West High School, which has a high rating, serves the area, and there are several private school options as well. The crime rate in Old Town is lower than the national average, contributing to its appeal for residents.

Frequently Asked Questions

What are the most popular neighborhoods for renters near Old Town?
The most popular neighborhoods for renters near Old Town are Mid Town and New Town.
What are the most popular zip codes for renters near Old Town?
The most popular zip codes for renters near Old Town is 33040.
How to Rent a Home