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Results: 769 Rentals

  • Villa Olivietta
    From $343 per night (USD)

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    Villa Olivietta

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! This ultimate ...

    From $343 per night (USD)

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  • CAROLINE ON MY MIND ~ Special!
    From $125 per night (USD)

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    "CAROLINE ON MY MIND" ~ Special!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    CLASSIC KEY WEST.... This retreat is an elegant two bedroom, 2 bath condominium one block off of famous Duval Street. Se ...

    From $125 per night (USD)

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  • Paradise Palm
    From $80 per night (USD)

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    Paradise Palm

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    4

    Paradise Palm***PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***This is a beautiful, private two-story open plan townhome ba ...

    From $80 per night (USD)

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  • Four Palms
    From $371 per night (USD)

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    Four Palms

    Bedrooms:
    5.5
    Bathrooms:
    3
    Sleeps:
    8

    WELCOME TO FOUR PALMS! We are complying with the directives listed on the Monroe County website. Please be aware tha ...

    From $371 per night (USD)

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    Details
  • Angler's Retreat
    From $207 per night (USD)

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    Angler's Retreat

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    A stay in Anglers Retreat is more then just a rental, but will be part of your Key West vacation experience. In addition ...

    From $207 per night (USD)

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  • Dance of the Butterflies
    From $181 per night (USD)

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    Dance of the Butterflies

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! For a month i ...

    From $181 per night (USD)

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  • Hemingway's Hammock
    From $171 per night (USD)

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    Hemingway's Hammock

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...

    From $171 per night (USD)

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  • The Contented Crane
    From $382 per night (USD)

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    The Contented Crane

    Bedrooms:
    4.5
    Bathrooms:
    3
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Traveling to ...

    From $382 per night (USD)

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  • Bahamian Bamboo
    From $452 per night (USD)

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    Bahamian Bamboo

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! BAHAMIAN BAMB ...

    From $452 per night (USD)

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  • Paradise On The Ocean
    From $414 per night (USD)

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    Paradise On The Ocean

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    5

    This two bedroom condo is located in the Truman Annex, Key West's premier residential community in Harbour Place on the ...

    From $414 per night (USD)

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  • MEMORY MAKER ~ Ideal Location!
    From $645 per night (USD)

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    "MEMORY MAKER" ~ Ideal Location!

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    4

    A STYLISH CARIBBEAN SURPRISE RIGHT OFF DUVAL... Private single-family home with peaceful porches totaling two bedrooms, ...

    From $645 per night (USD)

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  • Attitude Key West At the Beach
    From $165 per night (USD)

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    Attitude Key West At the Beach

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    We understand that these are unprecedented times and no one knows what tomorrow will bring. Here in Key West we believe ...

    From $165 per night (USD)

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  • Pineapple Cottage
    From $478 per night (USD)

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    Pineapple Cottage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    WELCOME TO PINEAPPLE COTTAGE! We are complying with the directives listed on the Monroe County website. Please be awa ...

    From $478 per night (USD)

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    Details
  • Somewhere on the beach
    From $288 per night (USD)

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    Somewhere on the beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Somewhere on the Beach has Amazing sweeping views of the Atlantic. This property has just undergone a major fantastic re ...

    From $288 per night (USD)

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  • Tim & Laura's Island Retreat
    From $120 per night (USD)

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    Tim & Laura's Island Retreat

    Bedrooms:
    2.5
    Bathrooms:
    2
    Sleeps:
    5

    Contact us about special Summer Rates! Absolute Best Location! Our Townhome is set in the tranquil verdant gardens of ...

    From $120 per night (USD)

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  • Vibe in Paradise Key West B217
    From $125 per night (USD)

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    Vibe in Paradise Key West B217

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This property features an extra large floor plan from the popular B building at 1800 Atlantic. Enjoy the flow through br ...

    From $125 per night (USD)

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  • Perfect Harmony
    From $142 per night (USD)

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    Perfect Harmony

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! PERFECT HARMO ...

    From $142 per night (USD)

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  • The Ibis & The Crane
    From $763 per night (USD)

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    The Ibis & The Crane

    Bedrooms:
    9
    Bathrooms:
    6
    Sleeps:
    16

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Dreaming of a ...

    From $763 per night (USD)

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  • Botanical Island Delight C120
    From $240 per night (USD)

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    Botanical Island Delight C120

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This unit has a king in both bedrooms. 1800 Atlantic is directly on the Atlantic ocean in Key West, adjacent to Smather ...

    From $240 per night (USD)

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  • Natures Preserve Tranquility A208
    From $161 per night (USD)

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    Natures Preserve Tranquility A208

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Lovely 2nd floor unit. Beautifully renovated, This unit has luxurious finishes. Both bedrooms and the living room open o ...

    From $161 per night (USD)

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  • Driftwood Dreams
    From $111 per night (USD)

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    Driftwood Dreams

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! This freshly ...

    From $111 per night (USD)

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  • A Toast to Sunset
    From $136 per night (USD)

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    A Toast to Sunset

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! If your idea ...

    From $136 per night (USD)

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  • Excitement on Key West Ocean
    From $274 per night (USD)

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    Excitement on Key West Ocean

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY You feel the excitement the moment you arrive. The war ...

    From $274 per night (USD)

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  • Azure Morning
    From $459 per night (USD)

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    Azure Morning

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Your spacious oceanfront balcony will be a front row seat for a panorama of azure blue ocean and sky. There are touches ...

    From $459 per night (USD)

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  • BELLA VITA ~ Location!
    From $250 per night (USD)

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    "BELLA VITA" ~ Location!

    Bedrooms:
    2.5
    Bathrooms:
    2
    Sleeps:
    4

    IDEAL LOCATION IN GREAT COMMUNITY... Enjoy your stay at the President's Walk at Truman Annex.  This well manicured commu ...

    From $250 per night (USD)

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  • The Artists' Muse
    From $584 per night (USD)

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    The Artists' Muse

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! For many, the ...

    From $584 per night (USD)

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  • Absolute Key West
    From $329 per night (USD)

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    Absolute Key West

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    4

    This Private home is located in the historic Truman Annex of old town Key West, where you can get away from it all while ...

    From $329 per night (USD)

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  • Southard Comfort in the Truman Annex
    From $207 per night (USD)

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    Southard Comfort in the Truman Annex

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    LOCATION, LOCATION, LOCATION and under new ownership. Southard Comfort is on Southard Street in the TRUMAN ANNEX, which ...

    From $207 per night (USD)

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  • Ocean Motion Too
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    Ocean Motion Too

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    7

    Have this yacht all to yourselves with its spacious and bright with windows surrounding it making views of the ocean ama ...

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  • Boathouse Harbor Retreat C337
    From $134 per night (USD)

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    Boathouse Harbor Retreat C337

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This property has been totally renovated and features a fantastic roll in custom shower which is fully wheelchair access ...

    From $134 per night (USD)

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  • Alhambra
    From $171 per night (USD)

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    Alhambra

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...

    From $171 per night (USD)

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  • Island Spa
    From $171 per night (USD)

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    Island Spa

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This Shipyard unit has a Queen bed, one bathroom, very sunny, bright condo.It has a very nice large deck balcony facing ...

    From $171 per night (USD)

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  • Sunset Dreams
    From $353 per night (USD)

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    Sunset Dreams

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! SUNSET DREAMS ...

    From $353 per night (USD)

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  • Casita Angelita
    From $218 per night (USD)

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    Casita Angelita

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! This moderniz ...

    From $218 per night (USD)

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  • Atlantic Paradise Found C232
    From $288 per night (USD)

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    Atlantic Paradise Found C232

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Atlantic Paradise Found C232 at 1800 Atlantic Condominiums is a beautifully appointed spacious condominium with a lovely ...

    From $288 per night (USD)

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  • Key West On My Mind 305
    From $288 per night (USD)

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    Key West On My Mind 305

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Stunning 2 bedroom ocean-view oasis vacation rental at the fabulous 1800 Atlantic in Key West. Our family owned unit has ...

    From $288 per night (USD)

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  • Banana Blossoms
    From $382 per night (USD)

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    Banana Blossoms

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! When explorin ...

    From $382 per night (USD)

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  • CARIBBEAN SOUL ~ Has it All!
    From $179 per night (USD)

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    "CARIBBEAN SOUL" ~ Has it All!

    Bedrooms:
    4.5
    Bathrooms:
    3
    Sleeps:
    6

    QUINTESSENTIAL KEY WEST HOME LEAVING NOTHING MORE TO BE DESIRED... Framed by a white picket fence you will be welcomed t ...

    From $179 per night (USD)

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  • Villa Aqua
    From $50 per night (USD)

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    Villa Aqua

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...

    From $50 per night (USD)

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  • Boli Townhouse in Key West
    From $75 per night (USD)

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    Boli Townhouse in Key West

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    We want you to know that your safety and comfort while in Key West is our utmost priority. We have upgraded our meticulo ...

    From $75 per night (USD)

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  • Tropical Executive
    From $414 per night (USD)

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    Tropical Executive

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...

    From $414 per night (USD)

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  • Waters Edge at Key Haven
    From $179 per night (USD)

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    Waters Edge at Key Haven

    Bedrooms:
    4.5
    Bathrooms:
    4
    Sleeps:
    8

    Spacious 2-story 4 bedroom, 3.5 bathroom home. This gulf front and canal front home has spectacular views and water acc ...

    From $179 per night (USD)

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  • Oceanfront
    From $100 per night (USD)

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    Oceanfront

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Discover the charm and grace of Old Key West in a new and distinctive setting. Luxury, two-bedroom, two-bath, waterfront ...

    From $100 per night (USD)

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  • Key West Home/Pool onthe Water
    From $239 per night (USD)

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    Key West Home/Pool onthe Water

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    BOAT LOVERS! Five minutes to open ocean. Keep your boat in the canal right at your back door. KAYAK LOVERS! Slip t ...

    From $239 per night (USD)

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  • BMW Fantasy
    From $300 per night (USD)

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    BMW Fantasy

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    Downtown Duval St. 2 bedroom 2 1/2 bath condo, located in the heart of Old Town. Walking distance to many of the main at ...

    From $300 per night (USD)

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  • The Commodore's Manor
    From $763 per night (USD)

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    The Commodore's Manor

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    14

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! THE COMMODORE ...

    From $763 per night (USD)

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  • Key West Suites Hotel #201
    From $234 per night (USD)

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    Key West Suites Hotel #201

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    6

    Key West Suites Hotel #201 Welcome to your charming private studio apartment right on Duval street! Built in 1919, it u ...

    From $234 per night (USD)

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  • CONCH HEAVEN ~ Easy Breezy!
    From $645 per night (USD)

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    "CONCH HEAVEN" ~ Easy Breezy!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    OLD TOWN LOCATION... A beautifully furnished and comfortable home, located a short distance from Duval Street.  Have bik ...

    From $645 per night (USD)

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  • Galleon Resort Waterfront Luxury in Old Town Key West
    From $350 per night (USD)

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    Galleon Resort Waterfront Luxury in Old Town Key West

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It ...

    From $350 per night (USD)

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  • Keys Kokomo
    From $185 per night (USD)

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    Keys Kokomo

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Get here fast ...

    From $185 per night (USD)

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  • Tom's Oceanfront Penthouse
    From $205 per night (USD)

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    Tom's Oceanfront Penthouse

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Covid Cancellation Policy: Until there is a Corona vaccine a 100% refund will be given up until the day of arrival. No ...

    From $205 per night (USD)

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  • Happy Hour Haven
    From $236 per night (USD)

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    Happy Hour Haven

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    It is always "Happy Hour" in this lovely second floor condo. Coffee in the morning, cocktails anytime, or just relax wi ...

    From $236 per night (USD)

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  • Key West State of Mind
    From $156 per night (USD)

    VRBO

    Key West State of Mind

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! KEY WEST STAT ...

    From $156 per night (USD)

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  • Boater's Dream at Sunset Marina
    From $117 per night (USD)

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    Boater's Dream at Sunset Marina

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    30- Night minimum stay: Private and quiet, this luxurious unit is an ideal place for relaxing and you are only minutes a ...

    From $117 per night (USD)

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  • Eisenhower Retreat
    From $599 per night (USD)

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    Eisenhower Retreat

    Bedrooms:
    4.5
    Bathrooms:
    4
    Sleeps:
    10

    A reflection of old Key West, Eisenhower's Retreat was designed and built with the architectural feel of an old "Conch H ...

    From $599 per night (USD)

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  • SUGAR SHACK ~ Escape Reality!
    From $250 per night (USD)

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    "SUGAR SHACK" ~ Escape Reality!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    PERFECT FAMILY RETREAT IN LUSH GATED COMMUNITY Enjoy this incredible family townhome in Coral Hammock’s lush community j ...

    From $250 per night (USD)

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  • Southernmost Sanctuary
    From $207 per night (USD)

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    Southernmost Sanctuary

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Southernmost Sanctuary is a beautiful two bedroom, one bath condominium has recently been updated located in the Shipyar ...

    From $207 per night (USD)

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  • Life in the Slow Lane
    From $300 per night (USD)

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    Life in the Slow Lane

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    4

    This charming unit has a whimsy nautical feel with the blue and white decor. There are two master suites, one on the ...

    From $300 per night (USD)

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  •  237 Southard Street, Key West
    From $125 per night (USD)

    VRBO

    237 Southard Street, Key West

    Bedrooms:
    2.5
    Bathrooms:
    2
    Sleeps:
    4

    Walk or take your bikes everywhere from this little part of Paradise, you will never need a car. Located in beautiful O ...

    From $125 per night (USD)

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  • Shady Nook
    From $207 per night (USD)

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    Shady Nook

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Two blocks away from Duval Street with direct access to Thomas Street through the rear gate. Has free hook up for intern ...

    From $207 per night (USD)

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  • Truman Treasure
    From $225 per night (USD)

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    Truman Treasure

    Bedrooms:
    5
    Bathrooms:
    3
    Sleeps:
    5

    Private home of three bedrooms and 2 1/2 Baths within a gated community. High definition TV found in every bedroom in ...

    From $225 per night (USD)

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  • Banyan Court 238
    From $100 per night (USD)

    VRBO

    Banyan Court 238

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This is a luxury town home, located in the heart of old town and walking distance to all main attractions, including th ...

    From $100 per night (USD)

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  • Atlantic Reflections
    From $302 per night (USD)

    VRBO

    Atlantic Reflections

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! ATLANTIC REFL ...

    From $302 per night (USD)

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  • Sailor's Story
    From $279 per night (USD)

    VRBO

    Sailor's Story

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...

    From $279 per night (USD)

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  • Atlantic Oasis Penthouse on the Ocean C420
    From $288 per night (USD)

    VRBO

    Atlantic Oasis Penthouse on the Ocean C420

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Penthouse property with vaulted ceilings at the famous 1800 Atlantic. Both bedrooms and the living room have access to y ...

    From $288 per night (USD)

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  • The Pearl in Paradise
    From $133 per night (USD)

    VRBO

    The Pearl in Paradise

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Located on a quiet street in Key West, a tranquil residential neighborhood located just behind the Key West Historical d ...

    From $133 per night (USD)

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  • Pelican Landing Antigua Retreat
    From $300 per night (USD)

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    Pelican Landing Antigua Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...

    From $300 per night (USD)

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  • Nature's Edge
    From $273 per night (USD)

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    Nature's Edge

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! NATURE'S EDGE ...

    From $273 per night (USD)

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  • SEAPORT SANCTUARY ~ Romantic!
    From $680 per night (USD)

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    "SEAPORT SANCTUARY" ~ Romantic!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    A QUIET BUNGALOW IN THE HISTORIC SEAPORT... Private one bedroom home in the heart of Old Town.  A great place for a coup ...

    From $680 per night (USD)

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  • Casa Manana Key West Monthly
    From $143 per night (USD)

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    Casa Manana Key West Monthly

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Casa Mañana at 800 Virginia Street is perfectly situated for the guest who wants to enjoy Key West at its finest. Locat ...

    From $143 per night (USD)

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  • Good Vibrations
    From $491 per night (USD)

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    Good Vibrations

    Bedrooms:
    5.5
    Bathrooms:
    4
    Sleeps:
    10

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Key West has ...

    From $491 per night (USD)

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  • The Simonton Studio
    From $45 per night (USD)

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    The Simonton Studio

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    2

    The Simonton Studio is neat, sweet and complete. This pet friendly accommodation is the perfect location for exploring ...

    From $45 per night (USD)

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  • William Skelton Home
    From $459 per night (USD)

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    William Skelton Home

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    14

    The William Skelton "Pink House" is located just steps from Duval Street in the heart of Old Town Key West. At this very ...

    From $459 per night (USD)

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  • BellaMaggio
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    BellaMaggio

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    11

    This yacht is one of a kind with its four state room layout, each room having its own private bath and shower. There is ...

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  • Pelican Landing Florida Retreat
    From $300 per night (USD)

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    Pelican Landing Florida Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...

    From $300 per night (USD)

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  • Archipelago
    From $557 per night (USD)

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    Archipelago

    Bedrooms:
    5.5
    Bathrooms:
    4
    Sleeps:
    12

    This gorgeous townhouse has 4 bedrooms, 4 full Bathrooms, and 2 half bathrooms. It is unique in that it has 2 of everyt ...

    From $557 per night (USD)

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  • Island Oasis
    From $205 per night (USD)

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    Island Oasis

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    WELCOME TO ISLAND OASIS! We are complying with the directives listed on the Monroe County website. Please be aware th ...

    From $205 per night (USD)

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  • Paradise Perfected
    From $182 per night (USD)

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    Paradise Perfected

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Hidden behind ...

    From $182 per night (USD)

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  • Villa Nomade at Shipyard Condominiums
    From $79 per night (USD)

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    Villa Nomade at Shipyard Condominiums

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Relax at Villa Nomade in luxurious surroundings. Featuring a fully equipped kitchen with bar seating and dining area. Th ...

    From $79 per night (USD)

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  • Studio Blu
    From $134 per night (USD)

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    Studio Blu

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in ...

    From $134 per night (USD)

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  • Another Day In Paradise
    From $207 per night (USD)

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    Another Day In Paradise

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...

    From $207 per night (USD)

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  • Colorful Cocktail
    From $279 per night (USD)

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    Colorful Cocktail

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This Shipyard unit is a two level condominium which has a private courtyard with a deck to enjoy the beautiful weather a ...

    From $279 per night (USD)

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  • Angel Fish
    From $279 per night (USD)

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    Angel Fish

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    Tropically decorated 2 bedroom 2 bathroom townhouse in secluded area of Truman Annex, complete with updated appliances, ...

    From $279 per night (USD)

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  • Shang-Ri-La
    From $218 per night (USD)

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    Shang-Ri-La

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! SHANG-RI-LA i ...

    From $218 per night (USD)

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  • Havana House
    From $204 per night (USD)

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    Havana House

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Located on So ...

    From $204 per night (USD)

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  • A Gulfstream Drift
    From $614 per night (USD)

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    A Gulfstream Drift

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    7

    Imagine yourself watching the sunset over the ocean from the huge penthouse balcony. This tropical retreat in Paradise h ...

    From $614 per night (USD)

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  • The “Lady Chelle”
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    The “Lady Chelle”

    Bedrooms:
    2.5
    Bathrooms:
    1
    Sleeps:
    4

    *Our boat is being cleaned according to CDC guidelines in order to ensure your safety and comfort throughout your v ...

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  • Pelican Landing Aruba Retreat
    From $300 per night (USD)

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    Pelican Landing Aruba Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...

    From $300 per night (USD)

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  • Noona's Mansion
    From $1908 per night (USD)

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    Noona's Mansion

    Bedrooms:
    6.5
    Bathrooms:
    6
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Located in Tr ...

    From $1908 per night (USD)

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  • Seascape
    From $207 per night (USD)

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    Seascape

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...

    From $207 per night (USD)

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  • Billy's Blue Heaven Condo
    From $342 per night (USD)

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    Billy's Blue Heaven Condo

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    BIlly's Blue Heaven is fresh, clean and Pristine. and Includes one private parking spot directly in front of the condo. ...

    From $342 per night (USD)

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  • Window On The Sea
    From $414 per night (USD)

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    Window On The Sea

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    5

    Wake up to beautiful views of the Gulf Waters in this 2 bedroom 2 bathroom condo in the highly coveted Harbor Place Cond ...

    From $414 per night (USD)

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  • BEACH HOUSE ~ Prestigious!
    From $300 per night (USD)

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    "BEACH HOUSE" ~ Prestigious!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    PRESTIGIOUS TROPICAL RETREAT... Indulge in this spectacular two-story home situated in the premier gated community of hi ...

    From $300 per night (USD)

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  • Charming Old Town Cottage
    From $200 per night (USD)

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    Charming Old Town Cottage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    This charming conch home is newly renovated. Classic wood frame with Two bedrooms and Two baths on the first floor as we ...

    From $200 per night (USD)

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  • Sunset Dalite
    From $414 per night (USD)

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    Sunset Dalite

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy the breathtaking views of the Atlantic Ocean and the Gulf of Mexico from your front row seat! | This gorgeous cond ...

    From $414 per night (USD)

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  • The Zesty Lime
    From $436 per night (USD)

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    The Zesty Lime

    Bedrooms:
    4.5
    Bathrooms:
    3
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Key West is k ...

    From $436 per night (USD)

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  • The Key West Hen
    From $175 per night (USD)

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    The Key West Hen

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Give me a call if you’d like to book our home 702-232-2750 Welcome to your home away from home and enter through the c ...

    From $175 per night (USD)

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  • Southernmost Palms
    From $300 per night (USD)

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    Southernmost Palms

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! When you thin ...

    From $300 per night (USD)

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  • THE FREE SPIRIT
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    THE FREE SPIRIT

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    PLEASE NOTE ... THIS YACHT IS CURRENTLY NOT FOR CHARTER. ALL INQUIRIES REGARDING CHARTERS WILL NOT BE ACKNOWLEDGED If ...

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  • Villa Alta
    From $50 per night (USD)

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    Villa Alta

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get wit ...

    From $50 per night (USD)

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