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Results: 716 Rentals

  • ** Waterfront - Two Blocks From Duval Street & Mallory Square**
    From $608 per night (USD)

    VRBO

    ** Waterfront - Two Blocks From Duval Street & Mallory Square**

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This condo located right on the water in Building 5 (Unit 531) - top floor - at the Hyatt Sunset Harbor, is a 2 bedroom, ...

    From $608 per night (USD)

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    Details
  • Historic District-Pool View-Duval Street-Beach Nearby-No Contact Check-In
    From $281 per night (USD)

    Expedia

    Historic District-Pool View-Duval Street-Beach Nearby-No Contact Check-In

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    This 2 bedroom, fully furnished condominium with brand new living room furniture and dining room table set is located in ...

    From $281 per night (USD)

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  • A PLEASANT STAY at The Truman Annex in Key West
    From $290 per night (USD)

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    A PLEASANT STAY at The Truman Annex in Key West

    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 $290 per night (USD)

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    Details
  • ANGEL FISH at The Truman Annex in Key West
    From $496 per night (USD)

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    ANGEL FISH at The Truman Annex in Key West

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $496 per night (USD)

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  • ABSOLUTE TRUMAN ANNEX in Key West
    From $541 per night (USD)

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    ABSOLUTE TRUMAN ANNEX in Key West

    Bedrooms:
    2
    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 $541 per night (USD)

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  • TROPICAL EXECUTIVE at The Truman Annex in Key West
    From $677 per night (USD)

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    TROPICAL EXECUTIVE at The Truman Annex in Key West

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $677 per night (USD)

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  • Paradise Island suite-2 bedroom 1 bath, a block off Duval St w/pool, parking
    From $629 per night (USD)

    VRBO

    Paradise Island suite-2 bedroom 1 bath, a block off Duval St w/pool, parking

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...

    From $629 per night (USD)

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  • Bimini suite-3 bedroom 3 bath, a block off Duval St w/pool, parking
    From $809 per night (USD)

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    Bimini suite-3 bedroom 3 bath, a block off Duval St w/pool, parking

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...

    From $809 per night (USD)

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    Details
  • Washer & Dryer, Near Downtown - Mesa House, Dos
    From $711 per night (USD)

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    Washer & Dryer, Near Downtown - Mesa House, Dos

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Whether you're lounging on the front porch or enjoying a seafood dinner inside, this 2-Bedroom Suite at The Mes ...

    From $711 per night (USD)

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  • Washer & Dryer, Near Downtown - Mesa House, Uno
    From $470 per night (USD)

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    Washer & Dryer, Near Downtown - Mesa House, Uno

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: Mesa House, Uno, is a charming condo in a prime location with a large front porch. Great for couples on a weeke ...

    From $470 per night (USD)

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    Details
  • Grand Bahama suite-3 bedroom 2 bath, a block off Duval St w/pool, parking
    From $808 per night (USD)

    VRBO

    Grand Bahama suite-3 bedroom 2 bath, a block off Duval St w/pool, parking

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...

    From $808 per night (USD)

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    Details
  • Nassau suite-2 bedroom 2 bath, a block off Duval St w/pool, parking
    From $624 per night (USD)

    Expedia

    Nassau suite-2 bedroom 2 bath, a block off Duval St w/pool, parking

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...

    From $624 per night (USD)

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    Details
  • “LOCATION”
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    “LOCATION”

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Fantastic Location. Only minutes from Duval St. Quaint 2 bd/ba with lots of space and a great kitchen. Short walk to mar ...

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  • SUN, SEA, AND SKY at The Truman Annex in Key West
    From $334 per night (USD)

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    SUN, SEA, AND SKY at The Truman Annex in Key West

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Sun Sea and Sky is blocks from bustling Duval Street, the heart of Old Town Key West, and an easy walk to restaurants, s ...

    From $334 per night (USD)

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  • Dog-friendly house + guesthouse with private hot tub - less than a mile to beach
    From $283 per night (USD)

    VRBO

    Dog-friendly house + guesthouse with private hot tub - less than a mile to beach

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Tropic Dream Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...

    From $283 per night (USD)

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  • ANGLER'S RETREAT at The Truman Annex in Key West
    From $413 per night (USD)

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    ANGLER'S RETREAT at The Truman Annex in Key West

    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 $413 per night (USD)

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    Details
  • A Seaglass Paradise at The Truman Annex in Key West
    From $396 per night (USD)

    VRBO

    A Seaglass Paradise at The Truman Annex in Key West

    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 $396 per night (USD)

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    Details
  • GREEN BAMBOO at The Truman Annex in Key West
    From $391 per night (USD)

    Expedia

    GREEN BAMBOO at The Truman Annex in Key West

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to Paradise! This 2 bedroom townhouse, featuring one bedroom with a king and the second bedroom features twin be ...

    From $391 per night (USD)

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    Details
  • CAPTAINS WHEEL at The Truman Annex in Key West
    From $580 per night (USD)

    VRBO

    CAPTAINS WHEEL at The Truman Annex in Key West

    Bedrooms:
    2
    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 $580 per night (USD)

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  • A LOW TIDE at The Truman Annex in Key West
    From $447 per night (USD)

    Expedia

    A LOW TIDE at The Truman Annex in Key West

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

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

    From $447 per night (USD)

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    Details
  • Steps from Duval with Private Pool – Southern Palms
    From $2791 per night (USD)

    VRBO

    Steps from Duval with Private Pool – Southern Palms

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    16

    Summary: Welcome to Southern Palms, the ultimate home base for your Key West adventure! Perfect for couples, friends, or ...

    From $2791 per night (USD)

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    Details
  • Key West Suites Hotel # 205
    From $1751 per night (USD)

    Expedia

    Key West Suites Hotel # 205

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

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

    From $1751 per night (USD)

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    Details
  • Key West Suites Hotel #201 on Duval
    From $1738 per night (USD)

    VRBO

    Key West Suites Hotel #201 on Duval

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

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

    From $1738 per night (USD)

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    Details
  • PELICAN'S PERCH at The Truman Annex in Key West
    From $462 per night (USD)

    Expedia

    PELICAN'S PERCH at The Truman Annex in Key West

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s Old Town neighborhood ...

    From $462 per night (USD)

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  • A SUNSET AND A HARBOUR VIEW at The Truman Annex in Key West
    From $743 per night (USD)

    VRBO

    A SUNSET AND A HARBOUR VIEW at The Truman Annex in Key West

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Exceptional accommodations, spectacular location and first class amenities await you and your group! This two bedroom, ...

    From $743 per night (USD)

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  • ANNIE'S HIDEAWAY at The Truman Annex in Key West
    From $437 per night (USD)

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    ANNIE'S HIDEAWAY at The Truman Annex in Key West

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This charming one bedroom, one bath 2nd floor property features an Olympic queen in the master bedroom and a large cover ...

    From $437 per night (USD)

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  • SALTY KISSES ~ Charming 2 Bedroom, 1.5 Bath Townhome in Truman Annex!
    From $276 per night (USD)

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    SALTY KISSES ~ Charming 2 Bedroom, 1.5 Bath Townhome in Truman Annex!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    PLEASE BE AWARE... We cannot accept a reservation of less than 28 nights after 12/22/25. You may book less than 28 nigh ...

    From $276 per night (USD)

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    Details
  • Secret Villa I @ Old Town with Private Pool, close to Duval!
    From $1226 per night (USD)

    Expedia

    Secret Villa I @ Old Town with Private Pool, close to Duval!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    - Secret Villa I - A Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own priv ...

    From $1226 per night (USD)

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    Details
  • Steps from Duval, Pool on Site & Bikes Included!
    From $233 per night (USD)

    VRBO

    Steps from Duval, Pool on Site & Bikes Included!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    ***Pool on Property and use of Free Bikes During your Stay!!!*** ***Contactless Check In and Check Out*** ***Enhanced Cl ...

    From $233 per night (USD)

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    Details
  • Heart of Old Town on QUIET Peacon Lane. Historic Seaport. Duval St. PETS WELCOME
    From $383 per night (USD)

    Expedia

    Heart of Old Town on QUIET Peacon Lane. Historic Seaport. Duval St. PETS WELCOME

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Single family home. (Not a condo.) We welcome kids, pets, partners, friends. Free off street parking for 2-3 vehicles. ...

    From $383 per night (USD)

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  • Carriage House at the Grand Maloney
    From $424 per night (USD)

    VRBO

    Carriage House at the Grand Maloney

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...

    From $424 per night (USD)

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    Details
  • Bunk Room at the Grand Maloney
    From $404 per night (USD)

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    Bunk Room at the Grand Maloney

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...

    From $404 per night (USD)

    Expedia

    Details
  • Unique Home with loft @ Truman Annex
    From $302 per night (USD)

    VRBO

    Unique Home with loft @ Truman Annex

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...

    From $302 per night (USD)

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    Details
  • MARLIN BLUE in the Truman Annex
    From $483 per night (USD)

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    MARLIN BLUE in the Truman Annex

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Make your special trip to paradise most memorable with a stay in your bright and airy Shipyard Unit. Located within Trum ...

    From $483 per night (USD)

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    Details
  • TROPICAL BREEZES at The Truman Annex in Key West
    From $380 per night (USD)

    VRBO

    TROPICAL BREEZES at The Truman Annex in Key West

    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 $380 per night (USD)

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    Details
  • MANATEE at The Truman Annex in Key West
    From $443 per night (USD)

    Expedia

    MANATEE at The Truman Annex in Key West

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    'Manatee' is a beautiful two bedroom, one bath, 1st floor condominium located within the prestigious gated community of ...

    From $443 per night (USD)

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  • ISLAND TIME at The Truman Annex in Key West
    From $380 per night (USD)

    VRBO

    ISLAND TIME at The Truman Annex in 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 $380 per night (USD)

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  • FunSeeker 1/2 block off Duval
    From $550 per night (USD)

    Expedia

    FunSeeker 1/2 block off Duval

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Only one block to the Hemingway House and two blocks to the Green Parrot bar! Restaurants, beaches, bars, entertainment ...

    From $550 per night (USD)

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  • Classic Key West condo w/ private parking, covered porches, & shared pool
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    Classic Key West condo w/ private parking, covered porches, & shared pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Cool Breeze Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...

    Click For Pricing

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  • Aah PARADISE at the Truman Annex in Old Town Key West
    From $610 per night (USD)

    Expedia

    Aah PARADISE at the Truman Annex in Old Town Key West

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $610 per night (USD)

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  • STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST.
    From $471 per night (USD)

    VRBO

    STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Note: In 2026, bookings will require a minimum stay of 28 days, starting on the first of the month. I can adjust the dat ...

    From $471 per night (USD)

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    Details
  • A LICENSE TO CHILL in the Truman Annex
    From $567 per night (USD)

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    A LICENSE TO CHILL in the Truman Annex

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $567 per night (USD)

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    Details
  • Bahama Palms
    From $258 per night (USD)

    VRBO

    Bahama Palms

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to “Bahama Palms” Key West! Newly renovated and full of Key West charm, this 2 bedroom 1 bath condo with washer ...

    From $258 per night (USD)

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    Details
  • Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex
    From $192 per night (USD)

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    Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This lovely Island Escape Condo is a upper level condo located in the prestigious Truman Annex. Not just another rental ...

    From $192 per night (USD)

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  • DOLPHIN WATCH in Key West @ The Truman Annex Compass Realty
    From $1148 per night (USD)

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    DOLPHIN WATCH in Key West @ The Truman Annex Compass Realty

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    VERY LUXURIOUS water front home located in the heart of downtown Key West within walking distance to all downtown attrac ...

    From $1148 per night (USD)

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    Details
  • AMBERJACK at The Truman Annex in Key West
    From $411 per night (USD)

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    AMBERJACK at The Truman Annex in Key West

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Recently refurbished throughout in a fun, tropical theme, Amberjack is situated on Southard Street in the exclusive gate ...

    From $411 per night (USD)

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  • CATCH OF THE DAY at The Truman Annex in Key West
    From $1056 per night (USD)

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    CATCH OF THE DAY at The Truman Annex in Key West

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    View passing ships and sunsets from your own first floor, large deck with plenty of seating for a large family in the Tr ...

    From $1056 per night (USD)

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    Details
  • SOUTHARD COMFORT at The Truman Annex in Key West
    From $438 per night (USD)

    Expedia

    SOUTHARD COMFORT at The Truman Annex in Key West

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    LOCATION, LOCATION, LOCATION! Southard Comfort is on Southard Street in the TRUMAN ANNEX, which is one of the most beau ...

    From $438 per night (USD)

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  • PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool!
    From $145 per night (USD)

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    PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool!

    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. One of ...

    From $145 per night (USD)

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    Details
  • Luxury Waterfront at Galion Resort in Old Town
    From $669 per night (USD)

    Expedia

    Luxury Waterfront at Galion Resort in Old Town

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    This condo is a 2BR/2BA Penthouse Loft on the 5th floor overlooking the marina. On the first floor is a full sized, ful ...

    From $669 per night (USD)

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    Details
  • Secret Villa II @ Old Town: with Private Pool, close to Duval!
    From $1238 per night (USD)

    VRBO

    Secret Villa II @ Old Town: with Private Pool, close to Duval!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    - Secret Villa II - A Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own pri ...

    From $1238 per night (USD)

    VRBO

    Details
  • PARADISE ON THE OCEANat The Truman Annex in Key West
    From $723 per night (USD)

    Expedia

    PARADISE ON THE OCEANat The Truman Annex in Key West

    Bedrooms:
    2
    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 $723 per night (USD)

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  • A SUNRISE COTTAGE at The Truman Annex in Key West
    From $467 per night (USD)

    VRBO

    A SUNRISE COTTAGE at The Truman Annex in Key West

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This charming 2 story 2 bedroom with loft, two bath cottage in the Shipyard Condominiums is located just off the pool an ...

    From $467 per night (USD)

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    Details
  • Cocktails & Dreams: Modern 2nd Floor Condo, Steps from Duval St, Seaport, Waterpark, Beach & Pool!
    From $414 per night (USD)

    Expedia

    Cocktails & Dreams: Modern 2nd Floor Condo, Steps from Duval St, Seaport, Waterpark, Beach & Pool!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    ***This unit holds a City of Key West Transient License and will be permitted to continue offering weekly rentals in 202 ...

    From $414 per night (USD)

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  • ALMOST PARADISE at The Truman Annex in Key West
    From $395 per night (USD)

    VRBO

    ALMOST PARADISE at The Truman Annex in Key West

    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 $395 per night (USD)

    VRBO

    Details
  • Private Parking, Heated Pool - Sweet Caroline
    From $832 per night (USD)

    Expedia

    Private Parking, Heated Pool - Sweet Caroline

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...

    From $832 per night (USD)

    Expedia

    Details
  • Private Parking , Heated Pool - Key Lime Cottage
    From $341 per night (USD)

    VRBO

    Private Parking , Heated Pool - Key Lime Cottage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...

    From $341 per night (USD)

    VRBO

    Details
  • Heated Pool, Epic Location - Sugar Pie Suite
    From $320 per night (USD)

    Expedia

    Heated Pool, Epic Location - Sugar Pie Suite

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...

    From $320 per night (USD)

    Expedia

    Details
  • Heated Pool, Epic Location - Honeybun Hideaway
    From $357 per night (USD)

    VRBO

    Heated Pool, Epic Location - Honeybun Hideaway

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...

    From $357 per night (USD)

    VRBO

    Details
  • Private Parking, Heated Pool - Banana Split
    From $519 per night (USD)

    Expedia

    Private Parking, Heated Pool - Banana Split

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...

    From $519 per night (USD)

    Expedia

    Details
  • Heated Pool, Private Parking - Creme Brulee Suite
    From $355 per night (USD)

    VRBO

    Heated Pool, Private Parking - Creme Brulee Suite

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...

    From $355 per night (USD)

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    Details
  • Near Duval: Hot Tub, Sleeps 6, Top Location
    From $938 per night (USD)

    Expedia

    Near Duval: Hot Tub, Sleeps 6, Top Location

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Just 30 seconds from vibrant Duval Street, this iconic conch home is your perfect Key West escape! With two bed ...

    From $938 per night (USD)

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    Details
  • Just steps to Duval- Sleeps 10- Pool House
    From $1237 per night (USD)

    VRBO

    Just steps to Duval- Sleeps 10- Pool House

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Summary: Located only 30 seconds from Duval Street, this house will be your Key West headquarters for bachelor parties, ...

    From $1237 per night (USD)

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  • Steps to Duval-Pool-Hot tub- Sleeps 16- BIG groups
    From $2914 per night (USD)

    Expedia

    Steps to Duval-Pool-Hot tub- Sleeps 16- BIG groups

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    16

    Summary: Perfect for bachelor and bachelorette parties, these 2 cottages that are quintessential Key West. Some of those ...

    From $2914 per night (USD)

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  • COLORFUL COCKTAIL in the Truman Annex
    From $524 per night (USD)

    VRBO

    COLORFUL COCKTAIL in the Truman Annex

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to your perfect Key West getaway! Nestled in the coveted Shipyard community of Truman Annex, this beautifully ma ...

    From $524 per night (USD)

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  • **BANANA BLOSSOMS @ THE ANNEX** Lush Villa by Beach + Pool + LAST KEY SERVICES
    From $696 per night (USD)

    Expedia

    **BANANA BLOSSOMS @ THE ANNEX** Lush Villa by Beach + Pool + LAST KEY SERVICES

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! When explorin ...

    From $696 per night (USD)

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  • A PALM OASIS at The Truman Annex in Key West.....
    From $666 per night (USD)

    VRBO

    A PALM OASIS at The Truman Annex in Key West.....

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    NEW LISTING!!! This charming two bedroom, two and one half bath townhome has recently been updated and added to our rent ...

    From $666 per night (USD)

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  • Coastal Inspired Cottage in Bahama Village Key West
    From $436 per night (USD)

    VRBO

    Coastal Inspired Cottage in Bahama Village Key West

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Bahama Dreams, a fully renovated 3 bedroom/ 2 bath eyebrow style home just two blocks off iconic Duval Street ...

    From $436 per night (USD)

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  • Bright Keys Cottage with Enclosed Yard, Deck, Porch, Partial, AC, & WiFi
    From $255 per night (USD)

    VRBO

    Bright Keys Cottage with Enclosed Yard, Deck, Porch, Partial, AC, & WiFi

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Key Rest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired d ...

    From $255 per night (USD)

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  • MONTHLY RENTAL, Thanksgiving 25 open, block to Duval, POOL, personal resort
    From $406 per night (USD)

    Expedia

    MONTHLY RENTAL, Thanksgiving 25 open, block to Duval, POOL, personal resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to "Shipwrecked in Paradise"! Historic Key West Eyebrow House with private pool..... ONE block to Duval, the He ...

    From $406 per night (USD)

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    Details
  • Luxury Waterfront Stay @ The Galleon, Mins from Downtown
    From $619 per night (USD)

    VRBO

    Luxury Waterfront Stay @ The Galleon, Mins from Downtown

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Imagine waking up every morning in Paradise. With Balconies that overlook the marina and ocean. Private marina, private ...

    From $619 per night (USD)

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  • CLASSIC KEY WEST - Grand home in Old Town location
    From $2752 per night (USD)

    VRBO

    CLASSIC KEY WEST - Grand home in Old Town location

    Bedrooms:
    7
    Bathrooms:
    7
    Sleeps:
    14

    The Mansion, circa 1840’s is a lovingly restored and renovated three story Classic Folk Victorian home with seven bedroo ...

    From $2752 per night (USD)

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  • PERFECTION...STEPS FROM DUVAL ~
    From $1122 per night (USD)

    VRBO

    PERFECTION...STEPS FROM DUVAL ~

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    The Villa is a newer built poolside home, situated steps away from famous Duval Street, the historic seaport and everyth ...

    From $1122 per night (USD)

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  • WATSON HOUSE GRAND ESTATE on Simonton St
    From $3953 per night (USD)

    VRBO

    WATSON HOUSE GRAND ESTATE on Simonton St

    Bedrooms:
    11
    Bathrooms:
    11
    Sleeps:
    22

    The Grand Estate is comprised of the Mansion and the Villa offering 11 bedrooms and baths. It is ideal for family gather ...

    From $3953 per night (USD)

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  • Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool
    From $695 per night (USD)

    VRBO

    Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Everything about this historic Key West tropical gem adds up to make a precious private garden cottage. Sitting in the m ...

    From $695 per night (USD)

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    Details
  • Lazy River Pool, Enchanting Garden, Old Town Key West, Free WiFi, Bikes & Parkin
    From $179 per night (USD)

    Expedia

    Lazy River Pool, Enchanting Garden, Old Town Key West, Free WiFi, Bikes & Parkin

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This beautifully home with quaint charm has a one month minimum stay requirement because of local zoning regulation. Col ...

    From $179 per night (USD)

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    Details
  • BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
    From $1110 per night (USD)

    VRBO

    BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    BEGIN YOUR ISLAND ESCAPE... Come get lost in the magic of this captivating island retreat offering modern amenities with ...

    From $1110 per night (USD)

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  • Snowbird-friendly condo with private balcony, garden views, W/D, on-site pool
    From $268 per night (USD)

    Expedia

    Snowbird-friendly condo with private balcony, garden views, W/D, on-site pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Happy Hour Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...

    From $268 per night (USD)

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  • **THE BEAMING BARRACUDA @ THE FOUNDRY** Near Duval & Beach + LAST KEY SERVICES…
    From $502 per night (USD)

    VRBO

    **THE BEAMING BARRACUDA @ THE FOUNDRY** Near Duval & Beach + LAST KEY SERVICES…

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! THE BEAMING B ...

    From $502 per night (USD)

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    Details
  • Sunset Harbor - Old Town Key West Location - Beautiful Property
    From $687 per night (USD)

    Expedia

    Sunset Harbor - Old Town Key West Location - Beautiful Property

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to the perfect location in old town Key West. Situated on the western side of the island, this resort is located ...

    From $687 per night (USD)

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    Details
  • The Galleon Resort Best Resort Location in Key West
    From $534 per night (USD)

    VRBO

    The Galleon Resort Best Resort Location in Key West

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    June unit 1bd 1ba with pull out sofa-sleeps 4, 5th floor with large balcony, great marina views. The Galleon Resort has ...

    From $534 per night (USD)

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  • Zen Cigar Maker Cottage, magical serpentine pool, serene landscaping, pkg/bikes
    From $406 per night (USD)

    VRBO

    Zen Cigar Maker Cottage, magical serpentine pool, serene landscaping, pkg/bikes

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to the Key West Shire! A sublime sanctuary where all your worldly troubles melt away and relaxation is paramoun ...

    From $406 per night (USD)

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    Details
  • Studio at Hyatt Residence Club Key West, Sunset Harbor.
    Click For Pricing

    VRBO

    Studio at Hyatt Residence Club Key West, Sunset Harbor.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Seth Nock Licensed Broker, Selling Timeshares INC. Studio at Hyatt Residence Club Key West, Sunset Harbor. Check-in: ...

    Click For Pricing

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  • SWEET'S SPOT at The Truman Annex in Key West
    From $508 per night (USD)

    Expedia

    SWEET'S SPOT at The Truman Annex in Key West

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    6

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

    From $508 per night (USD)

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  • Red Room at the Grand Maloney
    From $378 per night (USD)

    VRBO

    Red Room at the Grand Maloney

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...

    From $378 per night (USD)

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  • BEST TIME at The Truman Annex in Key West
    From $356 per night (USD)

    Expedia

    BEST TIME at The Truman Annex in Key West

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This newly renovated shipyard unit is a one level condominium on the second floor which has 2 decks to enjoy the beautif ...

    From $356 per night (USD)

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  • POOLSIDE HANGOVER at The Truman Annex in Key West
    From $433 per night (USD)

    VRBO

    POOLSIDE HANGOVER at The Truman Annex in Key West

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This is an amazing second floor two bedroom TWO BATH condo over by the gorgeous pool. Fully equipped for you to enjoy yo ...

    From $433 per night (USD)

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  • A Place on Emma at the Truman Annex in Key West
    From $1367 per night (USD)

    Expedia

    A Place on Emma at the Truman Annex in Key West

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Beautifully renovated & furnished 4 bedroom/ 4 bath single family home including a charming detached guest cottage is lo ...

    From $1367 per night (USD)

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  • SOUTHERNMOST SANCTUARY at The Truman Annex in Key West
    From $383 per night (USD)

    VRBO

    SOUTHERNMOST SANCTUARY at The Truman Annex in Key West

    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 $383 per night (USD)

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  • Incredible 2BR Penthouse condo on Front Street with amazing amenities!
    From $549 per night (USD)

    VRBO

    Incredible 2BR Penthouse condo on Front Street with amazing amenities!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The Galleon Resort is one of Key West's best resorts. Located on Front Street in front of the Marina, it has a large wat ...

    From $549 per night (USD)

    VRBO

    Details
  • Two Bed One Bath Ground Floor End Unit in the Heart of Old Town
    From $364 per night (USD)

    VRBO

    Two Bed One Bath Ground Floor End Unit in the Heart of Old Town

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    TRUMAN ANNEX: The Rooster Retreat is a lovely two bedroom, one bathroom ground floor end unit with a spacious backyard d ...

    From $364 per night (USD)

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  • **SALTWATER SAPPHIRE @ THE ANNEX** Stunning Private Home + LAST KEY SERVICES…
    From $937 per night (USD)

    Expedia

    **SALTWATER SAPPHIRE @ THE ANNEX** Stunning Private Home + LAST KEY SERVICES…

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! A highlight o ...

    From $937 per night (USD)

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  • Shipyard 276-Condo in Truman Annex-2 bedroom 2 bath, close to Duval w/ pool
    From $461 per night (USD)

    VRBO

    Shipyard 276-Condo in Truman Annex-2 bedroom 2 bath, close to Duval w/ pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...

    From $461 per night (USD)

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    Details
  • Unlock your Paradise Adventure - Between Sloppy Joe's and the Harbor
    From $394 per night (USD)

    Expedia

    Unlock your Paradise Adventure - Between Sloppy Joe's and the Harbor

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    This 4 story Townhouse is in "Old Town Villas". A Caribbean inspired community in the heart of Key West. Built in 2017. ...

    From $394 per night (USD)

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  • HIGH TIDE at The Truman Annex in Key West
    From $448 per night (USD)

    VRBO

    HIGH TIDE at The Truman Annex in Key West

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

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

    From $448 per night (USD)

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    Details
  • Historic Old Town Key West Rental Compound - 11 Beds, 4 Sleeper Sofas, 20 Guests
    From $4435 per night (USD)

    VRBO

    Historic Old Town Key West Rental Compound - 11 Beds, 4 Sleeper Sofas, 20 Guests

    Bedrooms:
    5
    Bathrooms:
    11
    Sleeps:
    20

    This private four (4) house compound accommodates (20) guests and is has a private 10′ x 25′ heated pool including a 5’ ...

    From $4435 per night (USD)

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    Details
  • A CONCH ESCAPE at The Truman Annex in Key West
    From $474 per night (USD)

    VRBO

    A CONCH ESCAPE at The Truman Annex in Key West

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Location, location, adorable two bedroom, one bath second floor condo overlooking the Truman Waterfront Park is the per ...

    From $474 per night (USD)

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    Details
  • A SUNSET VIEW at The Truman Annex in Key West
    From $416 per night (USD)

    Expedia

    A SUNSET VIEW at The Truman Annex in Key West

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

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

    From $416 per night (USD)

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  • PAPA'S CASITA in Key West
    From $368 per night (USD)

    VRBO

    PAPA'S CASITA in Key West

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Even Hemingway would have loved this place! Amazing renovation from top to bottom of this mid 1800's historic home locat ...

    From $368 per night (USD)

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  • GYPSY'S PALACE in the Truman Annex - Stunning ocean views!!
    From $367 per night (USD)

    Expedia

    GYPSY'S PALACE in the Truman Annex - Stunning ocean views!!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Fabulous waterfront two level condo in the beautiful Historic Mills Place Hospital Building in the Truman Annex awaits! ...

    From $367 per night (USD)

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