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$1,250,000
1401 Simonton Street 16
Key West, FL 33040
MLS# 618368
2 beds  |  2 baths  |  958 sqft

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Property Description
Luxury Condo Hotel with rare Transient Nightly Rental Rights - Exceptional Key West Value. Discover a rare opportunity to own a luxury condo-hotel residence in the heart of Key West with full transient nightly rental privileges - an increasingly scare asset class in the Florida Keys. This turnkey Investment generated almost $200,000 in actual gross rental revenue in 2005, offering strong income potential while preserving the true joy of ownership. Located at the iconic Santa Maria Resort, built in 2006 and consistently recognized as one of the Islands premier luxury resorts, this residence blends contemporary design with resort style comfort. This two bedroom, two bath residence is one of the few single-level units overlooking the resort style pool, capturing a serene sense of living rarely found in a condo hotel. Private poolside porch allows you to enjoy the relaxed sophistication of Island living - morning coffee, afternoon breezes and evenings wrapped in resort ambiance. Buyer can choose their own management company or choose to negotiate with the existing on-site company. All current reservations up to 180 days from closing must be honored. Being Sold Turn Key with all reservations in place allowing a seamless transition to the new owner. Resort Features include, Off Street Parking, 24 Hr Gym, Concierge, large Heated Pool and only One BLock To infamouns Duval St. This is not just an investment - it's a lifestyle-forward asset in one of the most supply-constrained markets in the country. Own a piece of Key West that pays you back, while still being yours to enjoy.

Details
Contract Information
Listing Board: Key West Association
Current Price: $1,250,000
Listing Date: 2026-01-28
List Price: $1,250,000
Location, Tax & Legal
KW Neighborhood: Old Town-S of Truman
Unit #: 16
City: KEY WEST
Mile Marker: 1
Marathon Neighborhood: N/A
Side: Ocean
Flood Zone: AE
Alternate Key #: 9087701
Parcel #: 00036231-001600
Zoning: HCT - Historic Commercial Tourist
Deed Restrictions: Unknown
Legal: UNIT 16 THE SANTA MARIA RESORT CONDOMINIUM OR2265-357/477 OR2272-1035 OR3126-1342
Taxes: 7984.55
Tax Year: 2025
Pub Sewer HkUp: Yes
Street #: 1401
Street Name: Simonton
Street Suffix: Street
Key/Island: Key West
State/Province: FL
Zip Code: 33040
County: Monroe
Subdivision: Filer Boyle Sub (1.0)
Area: 01 - Key West
General Property Description
Realtor.COM Type: Residential - Condo/Townhouse
Waterfront: No
Control Depth: 0
Lot Size: X
Lot SqFt: 0
Pool: Yes
Total Units: 0
SqFt Source: Property Data Card
Rentals Allowed: Yes
Style: Condo
Year Built: 2006
Living Apx SqFt: 958
Total Bedrooms: 2
Full Baths: 2
Total Baths: 2
Remarks & Misc
Remarks – Consumer: Luxury Condo Hotel with rare Transient Nightly Rental Rights - Exceptional Key West Value. Discover a rare opportunity to own a luxury condo-hotel residence in the heart of Key West with full transient nightly rental privileges - an increasingly scare asset class in the Florida Keys. This turnkey Investment generated almost $200,000 in actual gross rental revenue in 2005, offering strong income potential while preserving the true joy of ownership. Located at the iconic Santa Maria Resort, built in 2006 and consistently recognized as one of the Islands premier luxury resorts, this residence blends contemporary design with resort style comfort. This two bedroom, two bath residence is one of the few single-level units overlooking the resort style pool, capturing a serene sense of living rarely found in a condo hotel. Private poolside porch allows you to enjoy the relaxed sophistication of Island living - morning coffee, afternoon breezes and evenings wrapped in resort ambiance. Buyer can choose their own management company or choose to negotiate with the existing on-site company. All current reservations up to 180 days from closing must be honored. Being Sold Turn Key with all reservations in place allowing a seamless transition to the new owner. Resort Features include, Off Street Parking, 24 Hr Gym, Concierge, large Heated Pool and only One BLock To infamouns Duval St. This is not just an investment - it's a lifestyle-forward asset in one of the most supply-constrained markets in the country. Own a piece of Key West that pays you back, while still being yours to enjoy.
Directions: Located on Corner of Simonton and South
Association Info
Mandatory Home Owners Asc: Yes
1st Right of Refusal: No
Association Fee $: 3013.4
Assoc/Mnt Fee Per: Monthly
License Info
Transient Rntl Licns: Yes
Fee Includes
Bldg Exterior Mnt: 1
Building Insurance: 1
Common Area Mnt: 1
Dockage
None: 1
Tax Exemptions
None: 1
Appliances
Dishwasher: 1
Dryer: 1
Microwave: 1
Oven: 1
Range: 1
Refrigerator: 1
Stainless Steel Appliance(s): 1
Washer: 1
Cooling
Central Air: 1
Waterfront
None: 1
Waterview
No Waterview: 1
Neighborhood Feature
Beach: 1
Bike Paths: 1
Tennis Courts: 1
Interior Features
Built-in Cabinets: 1
Drapes/Blinds Incl: 1
Fire Sprinkler: 1
Granite Counter Top: 1
Window Treatments: 1
Property Condition
Updated/Remodeled: 1
Building Style
Above Flood: Yes
Vehicle Storage
Car(s): 1
Guest Parking: 1
Open Parking: 1
Off Street Parking: 1
Construction
CBS: 1
Concrete: 1
Land Size
Less Than 1/4 Acre: 1
Furnished
Furnished: 1
Utilities
FKAA: 1
Porch/Balcony
Open Porch/Balcony: 1
Exterior Features
Lanai: 1
Lighting: 1
Pool Info
In Ground: 1
Lap: 1
Heated: Yes
Pre-Wired
Cable: 1
Status Change Info
Status: Active
Property Features
Fee Includes: Bldg Exterior Mnt; Building Insurance; Common Area Mnt
Tax Exemptions: None
Waterfront: None
Waterview: No Waterview
Dockage: None
Property Condition: Updated/Remodeled
Vehicle Storage: Guest Parking; Off Street Parking; Open Parking
Furnished: Furnished
Cooling: Central Air
Utilities: FKAA
Interior Features: Built-in Cabinets; Drapes/Blinds Incl; Fire Sprinkler; Granite Counter Top; Window Treatments
Pre-Wired: Cable
Appliances: Dishwasher; Dryer; Microwave; Oven; Range; Refrigerator; Stainless Steel Appliance(s); Washer
Exterior Features: Lanai; Lighting
Pool Info: In Ground; Lap
Construction: CBS; Concrete
Neighborhood Feature: Beach; Bike Paths; Tennis Courts
Land Size: Less Than 1/4 Acre

Listing Office: Suzanne Moore Real Estate

Last Updated: January - 29 - 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.