Enter a destination to search

Key West: Vacation Rental By Owner

Search result 1 to 20 Of 1087
  • Property-1 Image 1
    House Select Dates for Price
    • 1Bed
    • 1Baths
    • (1) Exceptional
    Key West, FL

    This Shipyard unit has a Queen bed, one bathroom, very sunny, bright condo.It has a very nice large deck balcony facing Ft. Zachery, on the second level complete... ...more

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

    This Shipyard unit is a one level condominium on the second floor which has 2 decks to enjoy the beautiful weather and evening cocktails. This is a nicely... ...more

  • Property-3 Image 1
    House Select Dates for Price
    • 1Bed
    • 1Baths
    • (7) Excellent
    Key West, FL

    Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The condos are located 2 blocks from Duval... ...more

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

    Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The condos are located 2 blocks from Duval... ...more

  • Property-5 Image 1
    House Select Dates for Price
    • 1Bed
    • 1Baths
    • (7)
    Key West, FL

    Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The... ...more

  • Property-6 Image 1
    House Select Dates for Price
    • 2Bed
    • 1Baths
    • (7) Excellent
    Key West, FL

    Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The condos are located 2 blocks from Duval... ...more

  • Property-7 Image 1
    House Select Dates for Price
    • 2Bed
    • 3Baths
    • (1)
    Key West, FL

    This two bedroom condo is located in the Truman Annex, Key West's premier residential community in Harbour Place on the Atlantic Ocean front. All major rooms and... ...more

  • Property-8 Image 1
    House Select Dates for Price
    • 2Bed
    • 3Baths
    • (4)
    Key West, FL

    This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water and sunset views from your own private... ...more

  • Property-9 Image 1
    House Select Dates for Price
    • 4Bed
    • 4Baths
    • (4) Exceptional
    Key West, FL

    When you are seeking one of the best large home accommodations, look no further....you have found Admirals Treasure, a fabulous 4 bedroom, 4 bath home with it's... ...more

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

    This Private home is located in the historic Truman Annex of old town Key West, where you can get away from it all while being near the best that Key West has to... ...more

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

    In the same way Key West sunsets provide the perfect backdrop for a photo op, GOLDEN HOUR provides the perfect vacation setting for an unforgettable stay in... ...more

  • Property-12 Image 1
    House $5,234 / Nightly
    • 13Bed
    • 15Baths
    • (1) Exceptional
    Key West, FL

    Coordinating the entire gang for a dream Key West wedding, reunion, or simply a vacation of a lifetime is hard enough... let Last Key Realty make the... ...more

  • Property-13 Image 1
    House Select Dates for Price
    • 4Bed
    • 5Baths
    • (2) Excellent
    Key West, FL

    This ultimate Key West dream home is nestled in the highly desirable residential Old Town neighborhood of Solares Hill, just a quick walk from Duval Street and... ...more

  • Property-14 Image 1
    Condo Select Dates for Price
    • 3Bed
    • 2Baths
    • (5) Wonderful
    Key West, FL

    SUNSET DREAMS has everything you could want in a vacation home: it is very close to Old Town, so you'll be able to enjoy everything that Key West has to offer.... ...more

  • Property-15 Image 1
    Condo Select Dates for Price
    • 3Bed
    • 2Baths
    • (1) Exceptional
    Key West, FL

    SUNDRENCHED REFLECTIONS is very close to Old Town, with access to all the attractions that Key West has to offer. Yet, you'll be in your own world with a large... ...more

  • Property-16 Image 1
    Condo Select Dates for Price
    • 2Bed
    • 2Baths
    Key West, FL

    If your idea of a perfect Key West vacation is relaxing in an upscale condo centered around a breathtaking water view, A TOAST TO SUNSET is everything you are... ...more

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

    This freshly renovated condo is located at 1800 Atlantic Blvd on the beach, just steps from the Atlantic Ocean and sand in your toes. Enjoy quiet afternoons with... ...more

  • Property-18 Image 1
    House Select Dates for Price
    • 2Bed
    • 2Baths
    • (5) Wonderful
    Key West, FL

    THE CORAL FROG is a meticulously renovated and decorated one-story private home designed to be the resort-style haven you'd imagine yourself spending a month or... ...more

  • Property-19 Image 1
    House Select Dates for Price
    • 3Bed
    • 3Baths
    • (2) Exceptional
    Key West, FL

    PERFECT HARMONY is a newly updated home that embodies everything you could want in a vacation rental: comfort, privacy and a unique sense of tropical style. Most... ...more

  • Property-20 Image 1
    House Select Dates for Price
    • 5Bed
    • 6Baths
    • (3) Excellent
    Key West, FL

    On a quiet court just a short walk from Old Town and a block from the beach is CIELO TROPICALE, a stunning home completely hidden from the street by a high... ...more

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 January, where prices hit an average of $314 a night. In December, prices will hit an average low of $269 per night.