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    Key West, FL Hospitality Properties for Sale

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    Boutique Guesthouse in Old Town
    $11,500,000

    Boutique Guesthouse in Old Town

    412 Frances St, Key West, FL 33040

    Historic Key West guesthouse with 15 deluxe rooms.

    • Turnkey, fully furnished guesthouse with proven rental history, ensuring immediate income.
    • Prime location in the heart of Old Town Key West, walking distance to Duval Street and the Historic Seaport.
    • Licensed for 14 transient rentals, offering a steady stream of visitors.
    • Historic property listed on the National Register of Historic Places, adding unique character.
    • Features a serene heated pool, lush tropical gardens, and expansive covered porches.
    Updated: Sep 25, 2025
    View details
    Waterfront Property with Multifamily Units
    $4,750,000

    Waterfront Property with Multifamily Units

    901 Eisenhower Dr, Key West, FL 33040

    Historic Key West waterfront property with multifamily and commercial potential.

    • Waterfront property on a sprawling 15,609 sq ft lot zoned General Commercial, offering diverse development opportunities.
    • Legal five‑unit multi‑family configuration with a historic main house (4 units, 5 bedrooms, 4 bathrooms) and a separate cottage (2 bedrooms, 1 bathroom).
    • Prime location beside Garrison Bight, near Bayview Park and Tennis Courts.
    • Historic property built prior to 1912, held by the same family for over a century, offering unique Old Town charm.
    • Includes appliances: Dishwasher, Dryer, Range, Refrigerator, Washer.
    Updated: Dec 31, 2025
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    Key West Hotel/Motel Opportunity
    $19,550,000

    Key West Hotel/Motel Opportunity

    Hotel/Motel located in Old Town Key West, Florida.

    823 Fleming St, Key West, FL 33040
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    Waterfront Multi-Family Investment Opportunity
    $4,750,000
    3,788 SF

    Waterfront Multi-Family Investment Opportunity

    Historic Key West property with multi-family units and commercial zoning.

    901 Eisenhower Dr, Key West, FL 33040
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    Historic Key West Inn For Sale
    $20,350,000

    Historic Key West Inn For Sale

    38-room boutique hotel with historic charm and modern amenities.

    521 United St, Key West, FL 33040
    View details
    Based on your search, we've compiled 507 Potential Opportunities for your consideration. Besides 5 Active listings in Key West, FL, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 496 Off-Market properties to explore as potential leads, plus 2 Land Listings that present a potential for development.

    Explore Opportunities in Nearby Cities

    Here are 4 Similar properties we found in Nearby Locations for your consideration.

    Tranquility Bay Beach House Resort
    $520,000

    Tranquility Bay Beach House Resort

    Two-bedroom beach house with rental potential in lush resort area.

    2600 Overseas Hwy, Marathon, FL 33050
    View details
    Waterfront Redevelopment Opportunity with Dockage
    $3,549,000
    6,128 SF

    Waterfront Redevelopment Opportunity with Dockage

    Rare waterfront redevelopment opportunity with deep water dockage and highway frontage.

    14 125Th Street Gulf, Marathon, FL 33050
    View details
    Waterfront RV Lot with Boat Lift
    $395,000

    Waterfront RV Lot with Boat Lift

    Waterfront RV lot featuring a boat lift, dock, and full hookups.

    150 Smallwood Dr, Chokoloskee, FL 34138
    View details
    Chokoloskee RV Lot with Boat Slip
    $179,000

    Chokoloskee RV Lot with Boat Slip

    RV lot with boat slip in Outdoor Resorts Chokoloskee.

    150 Smallwood Dr, Chokoloskee, FL 34138
    View details

    Potential Development Sites for Consideration

    Can't find the perfect fit? These Land listings present an alternative path: the potential to develop a property for your specific goals.

    Important: These AI-suggestions are a starting point, not a guarantee of permitted use. All zoning, permitting, and land use information must be independently verified by you with the appropriate local authorities before making any commitments.

    Private Island Near Key West
    $7,950,000

    Private Island Near Key West

    Private island with beach, equestrian potential, and mainland access.

    7200 5Th St, Key West, FL 33040
    View details
    Private Island in Florida Keys
    $1,499,000

    Private Island in Florida Keys

    61.1-acre private island near Shark Key, Florida.

    Gulf Oharas Ky St, Key West, FL 33040
    View details

    Explore Off-Market Properties in Key West, FL

    Consider similar Off-Market properties in Key West, FL. You may contact the owners directly to inquire about their potential intentions to sell. To help you make a strong first impression, we can assist by reaching out to these owners with compelling proposals created using our AI tool.

    813 Simonton St

    813 Simonton St

    Hotels • 0.78 Acres
    Value Estimation by Request
    813 Simonton St, Key West, FL 33040
    View details
    525 United St

    525 United St

    Hotels • 0.50 Acres
    Value Estimation by Request
    525 United St, Key West, FL 33040
    View details
    413 Appelrouth Ln

    413 Appelrouth Ln

    Hotels • 0.46 Acres
    Value Estimation by Request
    413 Appelrouth Ln, Key West, FL 33040
    View details
    1102 Duval St, Unit G

    1102 Duval St, Unit G

    HOTEL/MOTEL • 835 SF
    Value Estimation
    $285,000
    1102 Duval St, Key West, FL 33040-3100
    View details
    1327 Duval St

    1327 Duval St

    HOTEL/MOTEL • 4,328 SF
    Value Estimation
    $550,000
    1327 Duval St, Key West, FL 33040-3131
    View details
    910 Simonton St, Unit 6

    910 Simonton St, Unit 6

    HOTEL/MOTEL • 528 SF
    Value Estimation
    $1,115,000
    910 Simonton St, Key West, FL 33040-7491
    View details
    3841 Roosevelt Blvd, Unit 323

    3841 Roosevelt Blvd, Unit 323

    HOTEL/MOTEL • 1,357 SF
    Value Estimation
    $795,000
    3841 Roosevelt Blvd, Key West, FL 33040-4534
    View details
    3841 Roosevelt Blvd, Unit 331

    3841 Roosevelt Blvd, Unit 331

    HOTEL/MOTEL • 1,357 SF
    Value Estimation
    $880,000
    3841 Roosevelt Blvd, Key West, FL 33040-4534
    View details
    200 Sunset Ln

    200 Sunset Ln

    HOTEL/MOTEL • 0.61 Acres
    Value Estimation
    $160,000
    200 Sunset Ln, Key West, FL 33040-8312
    View details
    2801 Roosevelt Blvd, Unit 38

    2801 Roosevelt Blvd, Unit 38

    HOTEL/MOTEL • 1,564 SF
    Value Estimation
    $265,000
    2801 Roosevelt Blvd, Key West, FL 33040-4073
    View details
    3841 Roosevelt Blvd, Unit 115

    3841 Roosevelt Blvd, Unit 115

    HOTEL/MOTEL • 1,357 SF
    Value Estimation
    $1,360,000
    3841 Roosevelt Blvd, Key West, FL 33040-4534
    View details
    2801 Roosevelt Blvd, Unit 27

    2801 Roosevelt Blvd, Unit 27

    HOTEL/MOTEL • 1,561 SF
    Value Estimation
    $280,000
    2801 Roosevelt Blvd, Key West, FL 33040-4073
    View details
    512 Petronia St

    512 Petronia St

    HOTEL/MOTEL • 836 SF
    Value Estimation
    $260,000
    512 Petronia St, Key West, FL 33040-7441
    View details
    2801 Roosevelt Blvd, Unit 26

    2801 Roosevelt Blvd, Unit 26

    HOTEL/MOTEL • 1,514 SF
    Value Estimation
    $280,000
    2801 Roosevelt Blvd, Key West, FL 33040-4073
    View details
    200 Sunset Ln

    200 Sunset Ln

    HOTEL/MOTEL • 0.16 Acres
    Value Estimation by Request
    200 Sunset Ln, Key West, FL 33040-8312
    View details
    1445 Roosevelt Blvd

    1445 Roosevelt Blvd

    HOTEL/MOTEL • 5.05 Acres
    Value Estimation
    $240,000
    1445 Roosevelt Blvd, Key West, FL 33040-4538
    View details
    617 Frnt St

    617 Frnt St

    HOTEL/MOTEL • 0.44 Acres
    Value Estimation
    $245,000
    617 Frnt St, Key West, FL 33040-6620
    View details
    2801 Roosevelt Blvd, Unit 40

    2801 Roosevelt Blvd, Unit 40

    HOTEL/MOTEL • 1,534 SF
    Value Estimation
    $280,000
    2801 Roosevelt Blvd, Key West, FL 33040-4073
    View details
    3841 Roosevelt Blvd, Unit 326

    3841 Roosevelt Blvd, Unit 326

    HOTEL/MOTEL • 1,357 SF
    Value Estimation
    $345,000
    3841 Roosevelt Blvd, Key West, FL 33040-4534
    View details

    Key West, FL Hospitality Properties Investment Opportunities Market Analysis

    Explore 501 hospitality properties for sale in Key West, FL, showcased through 5 active listings on our real estate platform. These investment opportunities span a total of 40,807,656 square feet of properties for sale, with an estimated market value of $217,170,000.

    Prices for hospitality properties in Key West, FL start at $195,000, averaging $775,607, and reaching up to $9,255,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you have the most current data.

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