1009 Whitehead Street
Key West, FL 33040
MLS# 620355
2 beds | 2 baths | 809 sqft
Property DescriptionIncome-Producing Transient Licensed Gem in the Heart of Old Town Key West! Rare opportunity to own a highly sought-after transient licensed vacation rental in one of Key West's most desirable Old Town locations. This charming 2-bedroom, 2-bath home also features a versatile bonus room, offering additional space for guests, a home office, or a creative retreat. Thoughtfully updated from top to bottom, the property boasts a new roof, A/C system, appliances, water heater, furniture, decking, pool and much more--providing a truly turnkey investment. A proven performer, this popular vacation rental enjoys strong occupancy, excellent reviews, and consistent income potential.
''Potter's Cottage'' a true Key West conch house, showcases artistic character and unique touches of the former owner who was a well known Key West potter, creating an authentic Key West experience that guests love. Outside, enjoy a beautifully refreshed salt water pool area, a covered lanai, an outdoor shower, new Trex decking, and inviting outdoor living spaces designed for relaxation and entertaining. The quaint front porch offers the perfect spot to unwind and soak in the vibrant neighborhood atmosphere. Ideally situated in the heart of Old Town, you're just steps from Duval Street, world-class dining, shopping, galleries, entertainment, and historic attractions. Leave the car behind--everything Key West has to offer is within easy walking or biking distance. Whether you're seeking a profitable investment, a personal island getaway, or the best of both worlds, this exceptional property delivers. A buyer can step into existing bookings and reputation on day one, proven 5.0 rating, 100 plus reviews and strong repeat bookings. Schedule your private showing today and discover this outstanding Key West opportunity.
Listing Board: Key West Association
As is Rght to Inspct: Yes
Current Price: $2,800,000
Listing Date: 2026-06-21
KW Neighborhood: Old Town-S of Truman
City: KEY WEST
Off Shore Island: No
Mile Marker: 1
Marathon Neighborhood: N/A
Side: Median
Flood Zone: 0.2 PCT ANNUAL CHANC
Alternate Key #: 1028100
Parcel #: 00027330-000000
Zoning: HMDR - Historic Medium Density Residential
Deed Restrictions: Unknown
Legal: KW SUB 8 PT LOT 3 SQR 3 TR 11 ZZ-130 OR575-208/11 OR771-1386 OR822-1408/09 OR843-1957 OR892-2034 OR999-1824 OR1124-1871
Taxes: 8455.65
Tax Year: 2025
Pub Sewer HkUp: Yes
Street #: 1009
Street Name: Whitehead
Street Suffix: Street
Key/Island: Key West
State/Province: FL
Zip Code: 33040
County: Monroe
Subdivision: Old Town - Unrecord (1.0)
Area: 01 - Key West
Realtor.COM Type: Residential - Single Family
Waterfront: No
Control Depth: 0
Lot Size: X
Lot Sqft Source: Tax Records
Total Units: 0
Acres: 0.03
SqFt Source: Unknown/Condo
Rentals Allowed: Yes
Min Rental Days: 1
Style: Single Family
Year Built: 1918
Living Apx SqFt: 809
Total Bedrooms: 2
Full Baths: 2
Total Baths: 2
Remarks – Consumer: Income-Producing Transient Licensed Gem in the Heart of Old Town Key West! Rare opportunity to own a highly sought-after transient licensed vacation rental in one of Key West's most desirable Old Town locations. This charming 2-bedroom, 2-bath home also features a versatile bonus room, offering additional space for guests, a home office, or a creative retreat. Thoughtfully updated from top to bottom, the property boasts a new roof, A/C system, appliances, water heater, furniture, decking, pool and much more--providing a truly turnkey investment. A proven performer, this popular vacation rental enjoys strong occupancy, excellent reviews, and consistent income potential.
''Potter's Cottage'' a true Key West conch house, showcases artistic character and unique touches of the former owner who was a well known Key West potter, creating an authentic Key West experience that guests love. Outside, enjoy a beautifully refreshed salt water pool area, a covered lanai, an outdoor shower, new Trex decking, and inviting outdoor living spaces designed for relaxation and entertaining. The quaint front porch offers the perfect spot to unwind and soak in the vibrant neighborhood atmosphere. Ideally situated in the heart of Old Town, you're just steps from Duval Street, world-class dining, shopping, galleries, entertainment, and historic attractions. Leave the car behind--everything Key West has to offer is within easy walking or biking distance. Whether you're seeking a profitable investment, a personal island getaway, or the best of both worlds, this exceptional property delivers. A buyer can step into existing bookings and reputation on day one, proven 5.0 rating, 100 plus reviews and strong repeat bookings. Schedule your private showing today and discover this outstanding Key West opportunity.
Mandatory Home Owners Asc: No
1st Right of Refusal: No
# of City License: 1
Transient Rntl Licns: Yes
Ceiling Fans(s): 1
Central Air: 1
Cathedral Ceilings: 1
Dade County Pine: 1
Drapes/Blinds Incl: 1
Granite Counter Top: 1
Above Flood: Unknown
Conch: 1
Impact Rstnce Doors: 1
Impact Rstnce Window: 1
FKAA: 1
Municipal Sewer: 1
Deck: 1
Open Porch/Balcony: 1
In Ground: 1
Salt Water: 1
Property Condition: Updated/Remodeled
Cooling: Ceiling Fans(s); Central Air
Utilities: FKAA; Municipal Sewer
Interior Features: Cathedral Ceilings; Dade County Pine; Drapes/Blinds Incl; Granite Counter Top
Appliances: Dishwasher; Dryer; Microwave; Oven; Refrigerator; Washer
Pool Info: In Ground; Salt Water; Decked
Land Size: Less Than 1/4 Acre
Terms: Cash; Conventional
Listing Office: Brenda Donnelly Real Estate LLC
Last Updated: June - 21 - 2026
The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.