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Results: 769 Rentals

  • Island Escape in Truman Annex
    From $100 per night (USD)

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    Island Escape in Truman Annex

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This lovely Island Escape Condo is a upper level condo located in the Truman Annex Shipyard a luxury gated community. No ...

    From $100 per night (USD)

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  • Smooth Sailing
    From $218 per night (USD)

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    Smooth Sailing

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $218 per night (USD)

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  • DREAM MAKER at 1800 ATLANTIC
    From $274 per night (USD)

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    DREAM MAKER at 1800 ATLANTIC

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY Let us help make your dreams come true: Enjoy your tr ...

    From $274 per night (USD)

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  • Gulfside Vistas
    From $436 per night (USD)

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    Gulfside Vistas

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

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

    From $436 per night (USD)

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  • La Vie En Rose
    From $389 per night (USD)

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    La Vie En Rose

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

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

    From $389 per night (USD)

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  • Sago Palm
    From $279 per night (USD)

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    Sago Palm

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    4

    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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  • Banana Breeze
    From $250 per night (USD)

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    Banana Breeze

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    "Banana Breeze" is an upscale escape by the sea, and considered by some to be a hidden gem. Tucked away in your own oasi ...

    From $250 per night (USD)

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  • CORAL CABANA ~ Tropical Comfort!
    From $228 per night (USD)

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    "CORAL CABANA" ~ Tropical Comfort!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    GATED COMMUNITY, CLOSE TO BOATING AND GOLFING... Coral Cabana, in the Coral Hammock Community is a gorgeous three bedroo ...

    From $228 per night (USD)

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  • 3/4 Time
    From $357 per night (USD)

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    3/4 Time

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    If you’re looking for an upscale escape by the sea, 3/4 Time is your Key West hidden gem. Enjoy the island life in your ...

    From $357 per night (USD)

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  • Riviera Americana
    From $294 per night (USD)

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    Riviera Americana

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

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

    From $294 per night (USD)

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  • Awake to the Morning Reflections C437
    From $134 per night (USD)

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    Awake to the Morning Reflections C437

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Beautifully renovated 2 bedroom 2 bath penthouse overlooking the Atlantic Ocean and Smathers Beach. Fabulous kitchen wit ...

    From $134 per night (USD)

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  • Dolphin Watch
    From $714 per night (USD)

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    Dolphin Watch

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    RECENTLY UPDATED & VERY LUXURIOUS water front home located in the heart of downtown Key West within walking distance to ...

    From $714 per night (USD)

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  • Key West Condo
    From $124 per night (USD)

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    Key West Condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This 2 bedroom (one King and one Queen, plus Queen size pull out couch in the living room), 2 bathroom unit offers all ...

    From $124 per night (USD)

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  • Blu On White
    From $300 per night (USD)

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    Blu On White

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    NEW ON THE RENTAL MARKET This recently renovated four bedroom, three bathroom traditional shotgun house with a twist, ha ...

    From $300 per night (USD)

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  • Starrs Atlantic Oasis C138
    From $143 per night (USD)

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    Starrs Atlantic Oasis C138

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Beautiful 2 bedroom 2 bath unit, with a lovely view of the Atlantic Ocean. This unit is an extra large floor plan with a ...

    From $143 per night (USD)

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  • Fun In The Sun
    From $279 per night (USD)

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    Fun In The Sun

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    This stately 2 bedroom townhouse in the President's Walk area of Porter Lane is furnished with tropical and luxury decor ...

    From $279 per night (USD)

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  • Viva Margarita!
    From $256 per night (USD)

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    Viva Margarita!

    Bedrooms:
    5.5
    Bathrooms:
    3
    Sleeps:
    8

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

    From $256 per night (USD)

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

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    Pelican Landing Dominica 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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  • La Grande Reunion
    From $566 per night (USD)

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    La Grande Reunion

    Bedrooms:
    6.5
    Bathrooms:
    5
    Sleeps:
    10

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

    From $566 per night (USD)

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  • Villa Bahama
    From $273 per night (USD)

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    Villa Bahama

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

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

    From $273 per night (USD)

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

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    Pelican Landing Abaco 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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  • Aquamarine Delight on the Ocean C333
    From $134 per night (USD)

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    Aquamarine Delight on the Ocean C333

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy ocean views from this bright and airy 3rd floor unit. This newly renovated unit comes fully equipped with attenti ...

    From $134 per night (USD)

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  • Queen Emma
    From $770 per night (USD)

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    Queen Emma

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    This beautifully finished and decorated four bedroom, three bath home has classic Key West architecture and is located o ...

    From $770 per night (USD)

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  • VILLAGE ROOSTER~Location!
    From $107 per night (USD)

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    "VILLAGE ROOSTER"~Location!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    BAHAMA VILLAGE TREASURE... This Old Town Key West home is just steps from the award winning restaurants and charming bou ...

    From $107 per night (USD)

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  • Sunset Reverie
    From $177 per night (USD)

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    Sunset Reverie

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $177 per night (USD)

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  • Blue Lagoon
    From $429 per night (USD)

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    Blue Lagoon

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This cheery property located on Southard Street features three bedrooms, one on the first level and two on on the second ...

    From $429 per night (USD)

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  • Poolside Hangover
    From $236 per night (USD)

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    Poolside Hangover

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This is an amazing two bedroom TWO BATH condo over by the gorgeous pool. Fully equipped for you to enjoy your time away ...

    From $236 per night (USD)

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  • Starshine Key West
    From $207 per night (USD)

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    Starshine Key West

    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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  • Eden @ The Annex
    From $273 per night (USD)

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    Eden @ The Annex

    Bedrooms:
    2.5
    Bathrooms:
    2
    Sleeps:
    5

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...

    From $273 per night (USD)

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  • PINEAPPLE COTTAGE ~ Relaxing!
    From $89 per night (USD)

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    "PINEAPPLE COTTAGE" ~ Relaxing!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    RELAXED DOWNTOWN LIVING... Envelop yourself in true island living in this cute cottage just for the two of you. Located ...

    From $89 per night (USD)

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  • Worlds End
    From $414 per night (USD)

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    Worlds End

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    5

    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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  • Latitude Adjustment @ Truman Annex
    From $300 per night (USD)

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    Latitude Adjustment @ Truman Annex

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    This Foundry townhouse is a Bostonian style 3 level home located in Old Town Key West. This home has been recently renov ...

    From $300 per night (USD)

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  • A Low Tide
    From $207 per night (USD)

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    A Low Tide

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    A Low Tide is a charming first floor end unit in the Shipyard Condominiums in the award wining gated community of the Tr ...

    From $207 per night (USD)

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  • Captains Wheel
    From $279 per night (USD)

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    Captains Wheel

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    This very popular getaway in the award-winning Truman Annex is a tropically decorated 2 bedroom, 2.5 bath town home feat ...

    From $279 per night (USD)

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  • LOST SHAKER OF SALT ~ Relax!
    From $695 per night (USD)

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    "LOST SHAKER OF SALT" ~ Relax!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    THE HEART OF OLD TOWN... Charming Old Town home in the heart of Key West.  Located on Southard Street just steps from Du ...

    From $695 per night (USD)

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  • Sun, Sea, And Sky
    From $171 per night (USD)

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    Sun, Sea, And Sky

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Sun Sea and Sky is only two blocks from bustling Duval Street, the heart of Old Town Key West, with an easy walk to rest ...

    From $171 per night (USD)

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  • Tropical Jewel
    From $228 per night (USD)

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    Tropical Jewel

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    WELCOME TO TROPICAL JEWEL! We are complying with the directives listed on the Monroe County website. Please be awar ...

    From $228 per night (USD)

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  • Royal Poinciena @ Truman Annex
    From $171 per night (USD)

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    Royal Poinciena @ Truman Annex

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    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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  • Galleon Resort Efficiency in Old Town
    From $171 per night (USD)

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    Galleon Resort Efficiency in Old Town

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    2

    This efficiency is located on the 5th floor of the Galleon Resort. One of only two efficiencies with both a king size b ...

    From $171 per night (USD)

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  • Archipelago II
    From $279 per night (USD)

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    Archipelago II

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    This newer renovation is a gorgeous 2 bedroom, 2.5 bath townhouse. The kitchen and baths are new and living room, dining ...

    From $279 per night (USD)

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  • Southernmost Solace
    From $109 per night (USD)

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    Southernmost Solace

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $109 per night (USD)

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  • Southernmost Bliss
    From $527 per night (USD)

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    Southernmost Bliss

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

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

    From $527 per night (USD)

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  • Away from it All
    From $207 per night (USD)

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    Away from it All

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Shipyard Condominiums ligger i det prestigefyllda gated community of Truman Annex i Key Wests gamla stadsdel. Condos li ...

    From $207 per night (USD)

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  • Brisa Fresca
    From $545 per night (USD)

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    Brisa Fresca

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

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

    From $545 per night (USD)

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  • Galleria Vacation Rental
    From $55 per night (USD)

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    Galleria Vacation Rental

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    2

    Quiet, quaint and conveniently located in the heart of key west. This small little studio is a great place to rest your ...

    From $55 per night (USD)

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  • Star of the Seaport
    From $872 per night (USD)

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    Star of the Seaport

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    12

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

    From $872 per night (USD)

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  • Sweet Home Angelita
    From $491 per night (USD)

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    Sweet Home Angelita

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    13

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

    From $491 per night (USD)

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  • Meyers Island Oasis on Atlantic B316
    From $125 per night (USD)

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    Meyers Island Oasis on Atlantic B316

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This is a lovely 3rd floor partial ocean-view unit. You will love the spacious 50 ft private balcony that runs the lengt ...

    From $125 per night (USD)

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  • Casa Coastal East C231
    From $125 per night (USD)

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    Casa Coastal East C231

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Casa Coastal East – C231 After a recent remodel of the kitchen and bath, this unit underwent a total makeover with its n ...

    From $125 per night (USD)

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  • The Royal Compound
    From $1526 per night (USD)

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    The Royal Compound

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    8

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

    From $1526 per night (USD)

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  • SERENITY~ Impeccable!
    From $1145 per night (USD)

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    "SERENITY"~ Impeccable!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    LOCAL LIVING.... Spend time relaxing in Paradise in the perfect home. Serenity is a beautifully decorated,  4 bedroom ho ...

    From $1145 per night (USD)

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  • Pelican Landing St.John Penthouse
    From $400 per night (USD)

    VRBO

    Pelican Landing St.John Penthouse

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

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

    From $400 per night (USD)

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  • Aah Paradise
    From $300 per night (USD)

    VRBO

    Aah Paradise

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    4

    AAH PARADISE This Foundry townhouse is a Bostonian style 3 level home located in Old Town Key West. This home has been r ...

    From $300 per night (USD)

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  • Old Town Suites - 2 Bedroom Suite, 1/2 block from Duval street
    From $50 per night (USD)

    VRBO

    Old Town Suites - 2 Bedroom Suite, 1/2 block from Duval street

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    This fully furnished 2nd level apartment features a sofa bed in the living area and fully-equipped kitchen. Located just ...

    From $50 per night (USD)

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  • Sweet Americana
    From $1304 per night (USD)

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    Sweet Americana

    Bedrooms:
    11
    Bathrooms:
    8
    Sleeps:
    20

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! It doesn't ge ...

    From $1304 per night (USD)

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  • GARDEN OASIS ~ Private!
    From $196 per night (USD)

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    "GARDEN OASIS" ~ Private!

    Bedrooms:
    4.5
    Bathrooms:
    4
    Sleeps:
    8

    WHEN ONLY THE BEST WILL DO... Located in the Casa Marina Area of Key West known for spacious and elegant fine homes; the ...

    From $196 per night (USD)

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  • BOOMERANG BOATHOUSE~ Charm!
    From $1295 per night (USD)

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    "BOOMERANG BOATHOUSE"~ Charm!

    Bedrooms:
    3.5
    Bathrooms:
    4
    Sleeps:
    8

    RETURN TO EQUANIMITY... “Boomerang Boathouse” is nestled in the peaceful neighborhood locals refer to as The Meadows.  T ...

    From $1295 per night (USD)

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  • Neptune's Penthouse
    From $240 per night (USD)

    VRBO

    Neptune's Penthouse

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $240 per night (USD)

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  • Key West Charm
    From $200 per night (USD)

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    Key West Charm

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Rent our house and enjoy all the charm Key West has to offer in our beautiful, newly renovated, decoratively appointed, ...

    From $200 per night (USD)

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  • SEA LA VIE~ Cozy Elegance!
    From $1455 per night (USD)

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    "SEA LA VIE"~ Cozy Elegance!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    THREE STORY GRANDEUR… Located in the Casa Marina District in Old Town.  This home is elegant, yet quite the tropical del ...

    From $1455 per night (USD)

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  • The Coral Frog
    From $272 per night (USD)

    VRBO

    The Coral Frog

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $272 per night (USD)

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  • La Casita En Cima
    From $124 per night (USD)

    VRBO

    La Casita En Cima

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $124 per night (USD)

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  • Papa's Casita
    From $683 per night (USD)

    VRBO

    Papa's Casita

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

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

    From $683 per night (USD)

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

    VRBO

    Pelican Landing Eleuthera 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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    Details
  • Historic Seaport Charmer
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    Historic Seaport Charmer

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Short one block walk to the harbor with great restaurants and bars. Park your car in the City Old Town Garage across the ...

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  • HEART OF OLD TOWN, KEY WEST!!
    From $125 per night (USD)

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    HEART OF OLD TOWN, KEY WEST!!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    La Dolce Vita is located in the heart of Old Town Key West and just steps to Duval Street in the heart of the Historic ...

    From $125 per night (USD)

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  • A Sanctuary Home
    From $134 per night (USD)

    VRBO

    A Sanctuary Home

    Bedrooms:
    3.5
    Bathrooms:
    3
    Sleeps:
    6

    A Sanctuary Home*****PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***** | Stay on the only 18-hole golf club in the Florida ...

    From $134 per night (USD)

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  • Foundry 7
    From $271 per night (USD)

    VRBO

    Foundry 7

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    5

    WELCOME TO FOUNDRY 7! We are complying with the directives listed on the Monroe County website. Please be aware that ...

    From $271 per night (USD)

    VRBO

    Details
  • SUNKISSED - Livin' off Duval!
    From $745 per night (USD)

    VRBO

    "SUNKISSED" - Livin' off Duval!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    7

    JUST OFF DUVAL... Private single family home with three bedrooms and three bathrooms.  Open the rear French doors to a p ...

    From $745 per night (USD)

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  • 1800 Atlantic Ocean Front Ste
    From $349 per night (USD)

    VRBO

    1800 Atlantic Ocean Front Ste

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Notice: Due to Corona Virus We suggest you purchase "Cancel For Any Reason Insurance". VRBO offers insurance at time of ...

    From $349 per night (USD)

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    Details
  • High Tide
    From $257 per night (USD)

    VRBO

    High Tide

    Bedrooms:
    2.5
    Bathrooms:
    2
    Sleeps:
    4

    If you have high expectations you are going to enjoy staying at High Tide. You are within walking distance to restaurant ...

    From $257 per night (USD)

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  • Sundrenched Reflections
    From $136 per night (USD)

    VRBO

    Sundrenched Reflections

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $136 per night (USD)

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  • A License To Chill
    From $300 per night (USD)

    VRBO

    A License To Chill

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    The historic Foundry, known as building #11, features three story townhomes, located in the award-winning residential ne ...

    From $300 per night (USD)

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  • All Together Now
    From $2507 per night (USD)

    VRBO

    All Together Now

    Bedrooms:
    16
    Bathrooms:
    13
    Sleeps:
    32

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

    From $2507 per night (USD)

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    Details
  • Latitude Penthouse Key West B417
    From $288 per night (USD)

    VRBO

    Latitude Penthouse Key West B417

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Top floor penthouse ocean-view condominium at 1800 Atlantic in the highly desirable B building. This unit has recently b ...

    From $288 per night (USD)

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  • The Lime & The Coconut
    From $872 per night (USD)

    VRBO

    The Lime & The Coconut

    Bedrooms:
    9
    Bathrooms:
    6
    Sleeps:
    16

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

    From $872 per night (USD)

    VRBO

    Details
  • Heavenly Zen
    From $472 per night (USD)

    VRBO

    Heavenly Zen

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

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

    From $472 per night (USD)

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    Details
  • STARFISH
    From $110 per night (USD)

    VRBO

    STARFISH

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    When choosing your dates, please keep in mind that we rent a minimum of 7 DAYS from SATURDAY to SATURDAY. (One exception ...

    From $110 per night (USD)

    VRBO

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  • Ocean Serenity C338 East
    From $161 per night (USD)

    VRBO

    Ocean Serenity C338 East

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This is a unique unit with an amazing view of the Atlantic ocean. Your home away from home, all the conveniences you wou ...

    From $161 per night (USD)

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    Details
  • The Grande Vista C432
    From $288 per night (USD)

    VRBO

    The Grande Vista C432

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The Grand Vista - 2 bedroom suite 2 Bedroom 2 bath suite, some renovations with flat screen plasma TV's in both bedro ...

    From $288 per night (USD)

    VRBO

    Details
  • Conch Casa Grande
    From $1417 per night (USD)

    VRBO

    Conch Casa Grande

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    8

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

    From $1417 per night (USD)

    VRBO

    Details
  • A Sunset And Harbour View
    From $614 per night (USD)

    VRBO

    A Sunset And Harbour View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Exceptional accommodations, spectacular location and first class amenities await you and your group! View passing ships ...

    From $614 per night (USD)

    VRBO

    Details
  • PELICAN
    From $110 per night (USD)

    VRBO

    PELICAN

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    When choosing your dates, please keep in mind that we rent a minimum of 7 DAYS from SATURDAY to SATURDAY. (One exception ...

    From $110 per night (USD)

    VRBO

    Details
  • A Bit of Aqua
    From $300 per night (USD)

    VRBO

    A Bit of Aqua

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to The Foundry a Bostonian style, 3 level townhouses that have been refurbished with tropical flair. Vaulted cei ...

    From $300 per night (USD)

    VRBO

    Details
  • Promenade to Paradise
    From $382 per night (USD)

    VRBO

    Promenade to Paradise

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

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

    From $382 per night (USD)

    VRBO

    Details
  • Bay Villas@Trumbo Point
    From $99 per night (USD)

    VRBO

    Bay Villas@Trumbo Point

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    Bay Villas is a charming 2-story waterfront condo located on Hilton Haven Road, a quiet cul-de-sac on Trumbo Point, whic ...

    From $99 per night (USD)

    VRBO

    Details
  • Pagitt House
    From $506 per night (USD)

    VRBO

    Pagitt House

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    WELCOME TO PAGITT HOUSE! We are complying with the directives listed on the Monroe County website. Please be aware ...

    From $506 per night (USD)

    VRBO

    Details
  • Moonlight Paradise C224
    From $280 per night (USD)

    VRBO

    Moonlight Paradise C224

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Moonlight" is a freshly renovated condo that is located at 1800 Atlantic Blvd on the beach, with sunset views right from ...

    From $280 per night (USD)

    VRBO

    Details
  • Flamingo Beach
    From $207 per night (USD)

    VRBO

    Flamingo Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    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)

    VRBO

    Details
  • Feeling Beachy in Key West B317
    From $143 per night (USD)

    VRBO

    Feeling Beachy in Key West B317

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Beautifully appointed 3rd floor ocean-view condo at the prestigious 1800 Atlantic Complex in Key West. This unit is an e ...

    From $143 per night (USD)

    VRBO

    Details
  • Bahama Tree house Studio
    From $75 per night (USD)

    VRBO

    Bahama Tree house Studio

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    2

    You will love this quiet tree-top studio in the heart of Old Town Key West. Located just a block away from the Historic ...

    From $75 per night (USD)

    VRBO

    Details
  • Island Breezes
    From $207 per night (USD)

    VRBO

    Island Breezes

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This charming second floor condominium features two bedrooms, and one full bath with views of the Truman Waterfront Park ...

    From $207 per night (USD)

    VRBO

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  • Flip Flop Retreat
    From $209 per night (USD)

    VRBO

    Flip Flop Retreat

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    5

    SPECIAL DISCOUNT FOR TAKING THE MONTH OF AUGUST 2021 - USE CONTACT BUTTON FOR DETAILS. Two bedroom, 2.5 bath townhome in ...

    From $209 per night (USD)

    VRBO

    Details
  • The Galleon Resort
    From $59 per night (USD)

    VRBO

    The Galleon Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Studio(lock-out) for rent 5th floor. The Galleon Resort has its own marina, fishing charters on-site, tiki bar that serv ...

    From $59 per night (USD)

    VRBO

    Details
  • Key West Sailing Adventure
    Click For Pricing

    VRBO

    Key West Sailing Adventure

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Hurry pick your last minute summer vacation package with sailing dates filling in fast! NOTE: MAKE SURE TO INSURE YOU ...

    Click For Pricing

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  • Saltwater Harmony
    From $283 per night (USD)

    VRBO

    Saltwater Harmony

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

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

    From $283 per night (USD)

    VRBO

    Details
  • Warm Waters
    From $159 per night (USD)

    VRBO

    Warm Waters

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    2 King Beds and a set of Twin Beds which can be converted to a King Bed. Lots of sleeping. Boating Boating Boating Qu ...

    From $159 per night (USD)

    VRBO

    Details
  • Pelican Landing Harbor Island Retreat
    From $300 per night (USD)

    VRBO

    Pelican Landing Harbor Island Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    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)

    VRBO

    Details
  • La Petite Penthouse
    From $273 per night (USD)

    VRBO

    La Petite Penthouse

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

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

    From $273 per night (USD)

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  • Saltwater Angler
    From $414 per night (USD)

    VRBO

    Saltwater Angler

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    5

    Large corner unit with three balconies and waterfront sunset view. Oversized living room with plenty of seating includin ...

    From $414 per night (USD)

    VRBO

    Details