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  • The Green House -Sunrise

    Key West, Florida

    Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of... ...more

    Beds: 1 Baths: 1 Property type: Apartment
    $266 / Nightly
  • Key West Condo close to the Ocean

    Key West, Florida

    This 2 bedroom, 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located just minutes from Smathers Beach, two miles from Higgs... ...more

    Beds: 2 Baths: 2 Property type: Condo (4) Exceptional
    $300 / Nightly
  • Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes

    Key West, Florida

    2 Bdrm, 1 Bath, Washer/dryer, Dishwasher, Great Porch View Of Southard St, PoolBRBRMultiple week and military discounts available. Great Fall rates! Queen bed in Master Bedroom, two single beds in... ...more

    Beds: 2 Baths: 1 Property type: Townhouse (4) Exceptional
    $315 / Nightly
  • Thomas Street

    Key West, Florida

    We hope you will enjoy this home where Ernest Hemingway and Jimmy Buffet memorabilia welcome you into the abode our first guest affectionately called “The Writer's Retreat'. This two bedroom, one... ...more

    Beds: 2 Baths: 1 Property type: House
    $300 / Nightly
  • Key West Island Vacation

    Key West, Florida

    YOUR PRIVATE GETAWAY IN KEY WEST, FLORIDA.  This beautifully historic 2 bedroom 2 bath home is conveniently located in Old Town Key West, FL. Just a short walk from everything you could dream of,... ...more

    Beds: 2 Baths: 2 Property type: House
    $419 / Nightly
  • Steps to Duval, Old Town Charm -Grand Bahama Suite

    Key West, Florida

    Just steps away from shops, restaurants, and the excitement of Duval Street, yet set on a quiet side street in a world of its own. With 3 bedrooms and 2 Baths, The Grand Bahama Suite has plenty... ...more

    Beds: 3 Baths: 2 Property type: Apartment (69) Excellent
    $329 / Nightly
  • The Green House - Sunset

    Key West, Florida

    Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of... ...more

    Beds: 1 Baths: 1 Property type: Apartment
    $266 / Nightly
  • Luxury Rental Old Town Key West Close to Beach. Private Heated Pool

    Key West, Florida

    Beautiful Keywest home blocks from Higgs Beach, playgrounds, restaurants, and famous Duval street. This rental includes use of 2 beach cruisers. Private Pool and front yard. Tropical Oasis.... ...more

    Beds: 3 Baths: 2 Property type: House (12) Excellent
    $429 / Nightly
  • LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!! SLEEPS 2-4, 3 BLKS TO BEACH

    Key West, Florida

    La Dolce Vita is just steps to Duval Street! "La Dolce Vita" is beautiful and is a totally renovated condo. Please check out our calendars for availability, photos and video. Everything... ...more

    Beds: 1 Baths: 1 Property type: Apartment (8) Exceptional
    $200 / Nightly
  • Ocean Vista

    Key West, Florida

    Modern 2 bedroom/2 bath condo with nice size balcony overlooks the Atlantic Ocean. California king bed in Master Bedroom and twin beds in the guest bedroom that can be converted into a king bed.... ...more

    Beds: 2 Baths: 2 Property type: Condo
    $299 / Nightly
  • Sunrise At Seaside Condo 2 bedroom 2 bath

    Key West, Florida

    Tropical 2 bedroom, 2 bath condo 1/2 mile from Smather's Beach in Key West. Fully appointed kitchen and living room. Balcony overlooking Salt Ponds and distant ocean view. Large heated pool... ...more

    Beds: 2 Baths: 2 Property type: Apartment (33) Excellent
    $149 / Nightly
  • Beautiful Mango House

    Key West, Florida

    Come stay at the Key West Mango Retreat! Live like a local Key Wester with your own tropical garden filled with banana, mango and papaya. Cool off in your private pool, and bike 5 minutes to world... ...more

    Beds: 2 Baths: 1 Property type: House
    $159 / Nightly
  • Bahama House - A++ Location with private pool/parking - walk to everything!

    Key West, Florida

    Location, location, location! Brand new and beautiful, this spacious house is conveniently located on a quiet street in the heart of Old Town Key West only 1/2 block from the fabulous shops,... ...more

    Beds: 3 Baths: 4 Property type: House
    $595 / Nightly
  • Seaside Condo 2 pools summer specials

    Key West, Florida

    This delightful sunny, quiet apartment is located across the street from Smathers beach and just a ten minute drive to Old Town. The apartment is set in a large lush tropical garden with two... ...more

    Beds: 1 Baths: 1 Property type: Condo (2) Exceptional
    $87 / Nightly
  • Elegant, Two Bedroom Condo Close to the Ocean

    Key West, Florida

    This quiet four-story condominium building is located just a short walk across the road to the Ocean with a recreational side walk miles long for running, walking, rollerblading and biking to... ...more

    Beds: 2 Baths: 2 Property type: Apartment (17) Very Good
    $300 / Nightly
  • Atlantis House Garden Suite

    Key West, Florida

    About us... #1 rated Guesthouse in Key West on TripAdvisor for 2016 and 2017! Romantic, Private, Boutique.... steps away from the Beach and Ocean and the Key West Marine Park. Free bike use, super... ...more

    Beds: 1 Baths: 1 Property type: Cottage
    $179 / Nightly
  • DISCOUNTED! 45' Luxury Yacht & Other Boats

    Key West, Florida

    This yacht is very spacious and bright with windows surrounding it making views of the ocean amazing. The marina and its grounds are meticulous and located in the middle of a turquoise paradise... ...more

    Beds: 2 Baths: 2 Property type: Yacht (2) Excellent
    $200 / Nightly
  • Center of It All - Paradise Island Suite

    Key West, Florida

    Relax of the Island Style front porch and enjoy Key West at it's finest. Centrally located, less than a block from Duval - this Completely updated 2 Bedroom, 1 Bath will simply amaze you! High... ...more

    Beds: 2 Baths: 1 Property type: Apartment (36) Exceptional
    $249 / Nightly
  • Olivia Place

    Key West, Florida

    Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderful home, which has recently been completely renovated, boasts 4 bedrooms,... ...more

    Beds: 4 Baths: 4 Property type: House
    $300 / Nightly
  • Key West Gulf front Home with private dock and pool.

    Key West, Florida

    Our beautiful, private home is located in a private, small subdivision with about 25 homes all on the open water, Gulf view. Its's a lovely home with 1 bedroom downstairs with a half bath and 2... ...more

    Beds: 3 Baths: 3 Property type: House
    $285 / Nightly

Key West: Vacation Rental By Owner

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.