218 Whitehead St, Key West, FL 33040
Property image
Property image
FOR RENT

$5,000/mo

Original price: $5,500
  • 3 Beds
  • 2 Baths
  • 1,407 sqft

218 Whitehead St, Key West, FL 33040

Truman Annex
Price may not include required fees and charges.
Cost and fees breakdown

Home Highlights

Central & Central Air
Single-Family Home

Local Information

  • Map ViewExplore the area around 218 Whitehead St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

About this House

Rare opportunity to lease a spacious 1,407-square-foot second-floor apartment in the heart of Old Town Key West. This 3-bedroom, 2-bath residence features an expansive open-concept floor plan, generous living and dining areas, and two private balconies overlooking one of the city's most iconic intersections. Filled with natural light and offering ample space for comfortable living, the apartment is ideally suited for employee housing or a long-term residence. Located at the corner of Whitehead Street and Front Street, tenants will enjoy immediate access to the Historic Seaport, Duval Street, world-class dining, shopping, and Key West's most popular attractions. A unique opportunity to lease a residence in one of the island's most desirable and walkable locations.

Details for 218 Whitehead St

Interior Features

Heating & Cooling
Heating: CentralAir ConditioningHeating Fuel: Central

Days on Market

Days on Market: 25 days on Trulia

Property Information

Year Built
Year Built: 1942
Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: Contact For Details

Agent Information

Listing Agent
MLS/Source ID: 620616
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Costs and Fees

Required monthly rent & fees
  • Base rent
    $5,000/mo
Required one-time fees
  • Security deposit
    Contact for details
  • Application fee
    Contact for details
  • Administrative fee
    Contact for details
Pricing is subject to change. All calculations are estimates and provided for informational purposes only. Actual amounts may include additional mandatory or optional fees. Please consult the community manager for a complete breakdown of all rental costs.
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Rental Market Trends in Truman Annex

Last updated Sep 2026
Trulia Rent Estimate$5,204/mo
Average rent
$6K
$1.4KMoM
Available listings
3
View rental market trends in Key West, FL

Around this home

Neighborhood Overview

Truman Annex
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Truman Annex

At least 1 Trulia users voted on each feature.

  • 100 % Say it's walkable to grocery stores

  • 100 % Say it's quiet

  • 100 % Say there's wildlife

  • 100 % Say neighbors are friendly

  • 100 % Say it's walkable to restaurants

  • 100 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "It’s a great neighborhood, we absolutely love having the opportunity to be able to live here!! We don’t have young kids so can’t really express things that are impt for them to know!!"
    1
    Flag
  • Langanlady
    "I have a 2 minute commute to the county courthouse. I could walk or bike but I am lazy and drive a car. "
    0
    Flag
  • Maya T.
    "This is the heart of historic Old Town Key West!"
    1
    Flag

Local Legal Protections

LGBTQ • Source of Income

Price and Tax history

DateEventPrice
Aug 18, 2026
Source: FLKMLS #620616
PriceChange
$5,000
Price decreased by 9%
Aug 13, 2026
Source: FLKMLS #620616
Listed For Rent
$5,500
Aug 12, 2026
Source: Zillow Rentals
ListingRemoved
$5,500
Jul 22, 2026
Source: Zillow Rentals
Listed For Rent
$5,500
Oct 19, 2009
Source: Agent Provided
ListingRemoved
$2,750,000
Berkshire Hathaway HomeServices Knight & Gardner Realty
Team GardnerLangley

Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
$180,000 PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.

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218 Whitehead St, Key West, FL is a 3 bedroom, 2 bathroom, 1,407 sqft single-family home built in 1942. 218 Whitehead St is located in Truman Annex, Key West. 218 Whitehead St was listed for rent for $5,000/month on Aug 13, 2026.