Key West: Vacation Rental By Owner

Showing 20 Of 1117 Vacation Rentals
  • Property-1 Image 1
    House $1,147 / Nightly
    • 2 Bed
    • 2 Baths
    Key West, FL

    About THE PROPERTY: Casablanca Grande consists of the two neighboring vacation rentals "Casablanca" & "Casablanca Too", located at the edge of Old Town Key West... ...more

  • Property-2 Image 1
    Condo $374 / Nightly
    • 3 Bed
    • 4 Baths
    Key West, FL

    THE PROPERTY: Welcome to Steamplant 207! Two Level, 5 Star Luxury Residence with breathtaking panoramic views of Key West. * Private Rooftop Terrace with... ...more

  • Property-3 Image 1
    House $1,925 / Nightly
    • 7 Bed
    • 5 Baths
    • (7) Exceptional
    Key West, FL

    About THE PROPERTY: Just steps from everything Key West, The Truman Suites consists of 5 separate fully equipped suites just a few steps from world famous Duval... ...more

  • Property-4 Image 1
    House $1,448 / Nightly
    • 3 Bed
    • 3 Baths
    • (84) Wonderful
    Key West, FL

    About THE PROPERTY: “Southard Comfort” is true Island living in Historic "Old Town" Key West. Nancy & Carl welcome you to their Key West vacation home! This... ...more

  • Property-5 Image 1
    Townhome $1,095 / Nightly
    • 2 Bed
    • 3 Baths
    • (136) Excellent
    Key West, FL

    Island Oasis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click "Book Now!" You'll... ...more

  • Property-6 Image 1
    Townhome $226 / Nightly
    • 2 Bed
    • 3 Baths
    • (11) Wonderful
    Key West, FL

    Tropical 2-story conch style townhome recently renovated and newly furnished located in the Key West Golf Club Resort. The home sleeps 4-6 comfortably for the... ...more

  • Property-7 Image 1
    House Select Dates for Price
    • 1 Bed
    • 1 Baths
    • (2) Exceptional
    Key West, FL

    YOU KAYAK TO THE BOAT. No frills, off-grid style accommodations! Budget "boat camping" for backpackers/adventures. The 22-foot sailboat is SMALL& all yours. It's... ...more

  • Property-8 Image 1
    Cottage Select Dates for Price
    • 1 Baths
    • (29) Excellent
    Key West, FL

    Great location, great price! Osprey is the perfect getaway rental for a couple who wants to enjoy everything Key West has to offer! This bright and colorful... ...more

  • Property-9 Image 1
    Townhome Select Dates for Price
    • 2 Bed
    • 3 Baths
    • (26)
    Key West, FL

    Craig & Cindy Truman Annex Foundry Townhouse is a 2 bedroom 2 1/2 bath townhouse in the best location in all of Key West....Truman Annex. We offer 2 Foundry... ...more

  • Property-10 Image 1
    Resort Select Dates for Price
    • 2 Bed
    • 2 Baths
    Key West, FL

    Thank you for Visiting Chimera Vacations LLC.! Please verify availability prior to booking. Inquire for exclusive rates or Feel free to request a custom rate... ...more

  • Property-11 Image 1
    Resort Select Dates for Price
    • 2 Bed
    • 2 Baths
    Key West, FL

    Thank you for Visiting Chimera Vacations LLC.! Please verify availability prior to booking. Inquire for exclusive rates or Feel free to request a custom rate... ...more

  • Property-12 Image 1
    House $279 / Nightly
    • 1 Bed
    • 1 Baths
    • (24) Excellent
    Key West, FL

    Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect setting for a laid back and quiet afternoon.... ...more

  • Property-13 Image 1
    House $405 / Nightly
    • 1 Bed
    • 1 Baths
    • (37) Wonderful
    Key West, FL

    Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect setting for a laid back and quiet afternoon.... ...more

  • Property-14 Image 1
    Apartment Select Dates for Price
    • 1 Baths
    • (62) Excellent
    Key West, FL

    Welcome to; Key West Beach Front Studio Attention; Spammers/hackers are slipping thru the cracks of this listing- typing """""Is your property... ...more

  • Property-15 Image 1
    House Select Dates for Price
    • 3 Bed
    • 4 Baths
    • (10) Exceptional
    Key West, FL

    About THE PROPERTY: VILLA LUXE reveals a discreet but sexy glamour beyond its gates––and it’s no wonder, since it was once owned by a hip clothing brand. It’s... ...more

  • Property-16 Image 1
    Apartment Select Dates for Price
    • 1 Bed
    • 1 Baths
    • (7) Exceptional
    Key West, FL

    About THE PROPERTY: Horse Conch is a Key West hidden gem located in perhaps the best location you could ask for. Nestled in the heart of Old Town Key West -... ...more

  • Property-17 Image 1
    House Select Dates for Price
    • 4 Bed
    • 2 Baths
    • (2) Exceptional
    Key West, FL

    About THE PROPERTY: Tucked back on a quiet Key West street, this spectacular 4 bedroom 2 bathroom home rests centrally located to many great shops, restaurants,... ...more

  • Property-18 Image 1
    House $2,120 / Nightly
    • 4 Bed
    • 5 Baths
    • (45)
    Key West, FL

    About THE PROPERTY: Villa Josine is an amazingly beautiful home located in one of the most sought after locations in Key West. The open-concept living and... ...more

  • Property-19 Image 1
    House Select Dates for Price
    • 2 Bed
    • 2 Baths
    • (4) Exceptional
    Key West, FL

    About THE PROPERTY: Lola's Place features everything you might want or need for your monthly vacation in Key West, starting with a private, off-street parking... ...more

  • Property-20 Image 1
    House Select Dates for Price
    • 1 Bed
    • 1 Baths
    • (33)
    Key West, FL

    About THE PROPERTY: Casablanca is the perfect get-a-way vacation rental for those seeking a good time, but would like to stay a distance from all the Duval... ...more

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Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Key West. Many accommodations in Key West provide "Non Smoking Only", there are 1174, or there are 1028 of Vacation Rentals in Key West with a "Pool - Spa", there are also 921 with "Children Welcome", which is another great reason to visit Key West.

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Key West. The most expensive month of the next 12 months is in July, where prices hit an average of $361 a night. In June, prices will hit an average low of $320 per night.