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Results: 758 Rentals

  • ~ CLOUD 9 ~ It's heaven on earth in this 3B\/3BA lavish home with pool\/parking
    From $2086 per night (USD)

    VRBO

    ~ CLOUD 9 ~ It's heaven on earth in this 3B\/3BA lavish home with pool\/parking

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    7

    THE PROPERTY: If you are looking for a peaceful retreat that is close to everything, this is the ultimate home for you. ...

    From $2086 per night (USD)

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    Details
  • ~ SEAS THE DAY ~ Nestled in a gated community by Fort Zachary Taylor beach!
    From $437 per night (USD)

    VRBO

    ~ SEAS THE DAY ~ Nestled in a gated community by Fort Zachary Taylor beach!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    **Home is available September 1 for a monthly rental (only). 28 night minimum** WEEKLY RENTAL: This property has a 7 n ...

    From $437 per night (USD)

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    Details
  • Very Rare-The Galleon 3 King Bd, 3 Bath w\/ 4th king bd in loft + sleeper sofa
    From $1038 per night (USD)

    VRBO

    Very Rare-The Galleon 3 King Bd, 3 Bath w\/ 4th king bd in loft + sleeper sofa

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    The Galleon Resort in Key West is a Perfect Resort for you, your Guests and your Family. The unit is spacious and very b ...

    From $1038 per night (USD)

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    Details
  • Key West Hen
    From $439 per night (USD)

    VRBO

    Key West Hen

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Give me a call if you have any questions! 702-232-3750 Welcome to your home away from home and enter through the canop ...

    From $439 per night (USD)

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    Details
  • Tropical State of Mind Key West FL
    From $795 per night (USD)

    VRBO

    Tropical State of Mind Key West FL

    Bedrooms:
    4
    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 $795 per night (USD)

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    Details
  • Key West 44ft Sailboat Wild Thing- stay 5 or more nights 1 night free!
    From $509 per night (USD)

    VRBO

    Key West 44ft Sailboat Wild Thing- stay 5 or more nights 1 night free!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Boats are located at the Perry Marina! Summer special starting 5/1/25 to 10/1/25 stay at docks we give you 5th free! We ...

    From $509 per night (USD)

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    Details
  • Beautiful sunsets!! Harbour Place, Truman Annex. Walk or bike to everything!
    From $2190 per night (USD)

    VRBO

    Beautiful sunsets!! Harbour Place, Truman Annex. Walk or bike to everything!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Harbor Place is one of the most prestigious properties in Key West! This unit offers breath taking water views overlook ...

    From $2190 per night (USD)

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    Details
  • Waterfront Views from Dolphin Watch
    From $1447 per night (USD)

    VRBO

    Waterfront Views from Dolphin Watch

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Dolphin Watch is located in prestigious Truman Annex and is one of the few private waterfront homes. We are less than tw ...

    From $1447 per night (USD)

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    Details
  • Location, Location, Location!!! Downtown Key West - Truman Annex!!!
    From $382 per night (USD)

    VRBO

    Location, Location, Location!!! Downtown Key West - Truman Annex!!!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    All the amenities of a fantastic resort suite and free assigned parking in the middle of everything in Key West...2/1 th ...

    From $382 per night (USD)

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    Details
  • Downtown Retreat - A++ Location W\/ Private Heated Pool\/Hot Tub
    From $1070 per night (USD)

    Expedia

    Downtown Retreat - A++ Location W\/ Private Heated Pool\/Hot Tub

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Location, location, location! Brand new and beautiful, this spacious house is conveniently located on a quiet street in ...

    From $1070 per night (USD)

    Expedia

    Details
  • Galleon Resort Efficiency Historic District
    From $493 per night (USD)

    VRBO

    Galleon Resort Efficiency Historic District

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    $25,00 Renovation completed end of 2016/beginning of 2017!! Different than ANY other Efficiency at the Galleon!! You w ...

    From $493 per night (USD)

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    Details
  • Rose Lane Villas - Villa Grande - 3 bedrooms - Downtown Key West
    From $1107 per night (USD)

    VRBO

    Rose Lane Villas - Villa Grande - 3 bedrooms - Downtown Key West

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    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 $1107 per night (USD)

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    Details
  • Large Floorplan & Yard, Sunny 2BR KING\/twin, 1 Bath, Truman Annx, Grd Flr, Pool
    From $414 per night (USD)

    VRBO

    Large Floorplan & Yard, Sunny 2BR KING\/twin, 1 Bath, Truman Annx, Grd Flr, Pool

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Amazing LOCATION! Truman Annex: SHABBY CHICKEN - come stay at the large & proud bird in town!! Large front yard and po ...

    From $414 per night (USD)

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    Details
  • Palm Trees Ocean Breeze Key West FL
    From $1261 per night (USD)

    VRBO

    Palm Trees Ocean Breeze Key West FL

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    Three bedroom, four bathroom private home with heated pool . Breathtaking sunsets can be seen from third floor deck over ...

    From $1261 per night (USD)

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    Details
  • Truman Annex - Beautiful Townhome - President's Lane
    From $362 per night (USD)

    VRBO

    Truman Annex - Beautiful Townhome - President's Lane

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Beautiful 2-story townhouse; master bedroom with King Bed and double doors to deck; full bath; second bedroom with two t ...

    From $362 per night (USD)

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    Details
  • ​Tranquil 2-BR Condo in Truman Annex, Steps to Pool & 5-Min Walk to Duval St.
    From $293 per night (USD)

    VRBO

    ​Tranquil 2-BR Condo in Truman Annex, Steps to Pool & 5-Min Walk to Duval St.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to our lovely condo which is located in the famed Truman Annex Complex right in the heart of fabulous Key West. ...

    From $293 per night (USD)

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    Details
  • Key West, Gated Truman Annex Condo, new Waterfront Park, and Ft. Zach  Beach.
    From $326 per night (USD)

    VRBO

    Key West, Gated Truman Annex Condo, new Waterfront Park, and Ft. Zach Beach.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This condo has a unique location in the Gated Truman Annex. It is very quiet, but yet very close to all Key West has t ...

    From $326 per night (USD)

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    Details
  • Truman Annex Best Location in Town
    From $430 per night (USD)

    VRBO

    Truman Annex Best Location in Town

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    We stick to a Saturday check in during the in season months (Jan-April) Greetings from Paradise, where the temperature ...

    From $430 per night (USD)

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    Details
  • Miami Vice Sailboat Used For TV Series Ready To Charter! Includes 2 Hour Sail
    From $566 per night (USD)

    VRBO

    Miami Vice Sailboat Used For TV Series Ready To Charter! Includes 2 Hour Sail

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    *Our business is now in a pristine marina at the stock island division in Key West. Perry Marina has a shuttle that ru ...

    From $566 per night (USD)

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    Details
  • SUMMER LOVIN~Incredibly Located 3 Bedroom, 3 Bathroom Home w\/ Pool!
    From $429 per night (USD)

    Expedia

    SUMMER LOVIN~Incredibly Located 3 Bedroom, 3 Bathroom Home w\/ Pool!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    SIMPLY CHARMING... An ideal way to spend your tropical vacation immersed in this historic, charming abode showcasing mod ...

    From $429 per night (USD)

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    Details
  • Old Town Beauty built in 1883
    From $182 per night (USD)

    VRBO

    Old Town Beauty built in 1883

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Enjoy the lovely Key West ocean breeze from your private Tree House. This is the quietest area of Old Town but only4 blo ...

    From $182 per night (USD)

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    Details
  • Rose Lane Villas - Villa Rosa - 1 Bedroom - Downtown Key West
    From $579 per night (USD)

    VRBO

    Rose Lane Villas - Villa Rosa - 1 Bedroom - Downtown Key West

    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 $579 per night (USD)

    VRBO

    Details
  • Villa Mer at Shipyard Condominiums
    From $376 per night (USD)

    VRBO

    Villa Mer at Shipyard Condominiums

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Relax at Villa Mer in luxurious surroundings. Renovated in 2019 it has a fully equipped kitchen with bar seating. The li ...

    From $376 per night (USD)

    VRBO

    Details
  • A Touch Of Cuba In Key West
    From $449 per night (USD)

    VRBO

    A Touch Of Cuba In Key West

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Conch Republic and the Shipyard section of the Truman Annex. You have many choices of accommodations and sin ...

    From $449 per night (USD)

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    Details
  • Rose Lane Villas - Villa Porta - 1 Bedroom - Downtown Key West
    From $493 per night (USD)

    VRBO

    Rose Lane Villas - Villa Porta - 1 Bedroom - Downtown Key West

    Bedrooms:
    1
    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 $493 per night (USD)

    VRBO

    Details
  • A Touch of Bermuda at Truman Annex
    From $477 per night (USD)

    VRBO

    A Touch of Bermuda at Truman Annex

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Envision yourself relaxing in a beautiful wood framed conch cottage with overhead fans lazily turning below the sloping ...

    From $477 per night (USD)

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    Details
  • Key West Suites Hotel - Adam Scott Rote Suite
    From $2183 per night (USD)

    VRBO

    Key West Suites Hotel - Adam Scott Rote Suite

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used to be called the Central ...

    From $2183 per night (USD)

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    Details
  • Key West Rooster
    From $444 per night (USD)

    VRBO

    Key West Rooster

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Please call or text if you’d like to book our home 702 232... 3750 When booking our home please include a brief descri ...

    From $444 per night (USD)

    VRBO

    Details
  • Rare Penthouse 2 bed\/2bath additional King in loft
    From $1238 per night (USD)

    VRBO

    Rare Penthouse 2 bed\/2bath additional King in loft

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Perfect vacation rental that allows you to enjoy breakfast on your private balcony, unwind and relax in the master bath ...

    From $1238 per night (USD)

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    Details
  • The Galleon Resort in Beautiful Key West. Amazing Views! 2 bedroom villa!
    From $913 per night (USD)

    VRBO

    The Galleon Resort in Beautiful Key West. Amazing Views! 2 bedroom villa!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Concierge Realty is proud to present luxury villas at The Galleon Resort! **Reservations are available in weekly (7 nig ...

    From $913 per night (USD)

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    Details
  • Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West
    From $789 per night (USD)

    VRBO

    Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West

    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 $789 per night (USD)

    VRBO

    Details
  • Villa Fleur at Shipyard Condominiums
    From $366 per night (USD)

    VRBO

    Villa Fleur at Shipyard Condominiums

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Relax at Villa Fleur in luxurious surroundings. Renovated in 2018 it has a fully equipped kitchen with bar seating and d ...

    From $366 per night (USD)

    VRBO

    Details
  • BEACH HOUSE ~ Stunning 4B\/4Ba Home with Private Pool in Truman Annex!
    From $1565 per night (USD)

    VRBO

    BEACH HOUSE ~ Stunning 4B\/4Ba Home with Private Pool in Truman Annex!

    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 $1565 per night (USD)

    VRBO

    Details
  • Galleon Resort Efficiency in the old town
    From $317 per night (USD)

    Expedia

    Galleon Resort Efficiency in the old town

    Bedrooms:
    1
    Bathrooms:
    1
    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 $317 per night (USD)

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    Details
  • Raphael Suite: 2\/2 Studio Rooms - Pool, Patio w\/grill, 2 blocks from Duval!
    From $605 per night (USD)

    VRBO

    Raphael Suite: 2\/2 Studio Rooms - Pool, Patio w\/grill, 2 blocks from Duval!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    The Galleria was once a haven for traveling artists who frequented Key West. With a tranquil pool area and spacious pati ...

    From $605 per night (USD)

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    Details
  • Pet Friendly Studio Near Duval – Traveler's Palm
    From $485 per night (USD)

    Expedia

    Pet Friendly Studio Near Duval – Traveler's Palm

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Summary: Get ready to dive into the vibrant energy of Key West at Traveler's Palm! This recently updated, spacious secon ...

    From $485 per night (USD)

    Expedia

    Details
  • Studio, Pet Friendly & Near Downtown - Coral Cove
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    VRBO

    Studio, Pet Friendly & Near Downtown - Coral Cove

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Micro-efficiency near downtown Key West! The Galleria was once a haven for traveling artists who frequented K ...

    Click For Pricing

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    Details
  • Washer & Dryer, Near Downtown - Mesa House, Uno
    From $444 per night (USD)

    Expedia

    Washer & Dryer, Near Downtown - Mesa House, Uno

    Bedrooms:
    1
    Bathrooms:
    2
    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 $444 per night (USD)

    Expedia

    Details
  • Steps from Duval, Pool on Site & Bikes Included!
    From $328 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 $328 per night (USD)

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    Details
  • Hot Tub & Pet Friendly - Royal Palm
    From $440 per night (USD)

    Expedia

    Hot Tub & Pet Friendly - Royal Palm

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Royal Palm is a beautiful newly updated studio cottage tucked away in the heart of Old Town Key West. There is ...

    From $440 per night (USD)

    Expedia

    Details
  • Deluxe Queen & Pet Friendly - Curry Mansion Inn
    From $332 per night (USD)

    VRBO

    Deluxe Queen & Pet Friendly - Curry Mansion Inn

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...

    From $332 per night (USD)

    VRBO

    Details
  • Classic King, Pool - Curry Mansion Inn
    From $355 per night (USD)

    Expedia

    Classic King, Pool - Curry Mansion Inn

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...

    From $355 per night (USD)

    Expedia

    Details
  • Classic King, Pool - Curry Mansion Inn
    From $377 per night (USD)

    VRBO

    Classic King, Pool - Curry Mansion Inn

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...

    From $377 per night (USD)

    VRBO

    Details
  • Classic King & Private Balcony - Curry Mansion Inn
    From $369 per night (USD)

    Expedia

    Classic King & Private Balcony - Curry Mansion Inn

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...

    From $369 per night (USD)

    Expedia

    Details
  • Classic King & Private Balcony - Curry Mansion Inn
    From $369 per night (USD)

    VRBO

    Classic King & Private Balcony - Curry Mansion Inn

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...

    From $369 per night (USD)

    VRBO

    Details
  • Deluxe King, Pet Friendly &  - Curry Mansion Inn
    From $372 per night (USD)

    Expedia

    Deluxe King, Pet Friendly & - Curry Mansion Inn

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...

    From $372 per night (USD)

    Expedia

    Details
  • King Suite with Balcony - The James House
    From $384 per night (USD)

    VRBO

    King Suite with Balcony - The James House

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...

    From $384 per night (USD)

    VRBO

    Details
  • Deluxe King with Balcony - The James House
    From $396 per night (USD)

    Expedia

    Deluxe King with Balcony - The James House

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...

    From $396 per night (USD)

    Expedia

    Details
  • Classic King & Private Balcony - Curry Mansion Inn
    From $383 per night (USD)

    VRBO

    Classic King & Private Balcony - Curry Mansion Inn

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...

    From $383 per night (USD)

    VRBO

    Details
  • Classic King, Pool - Curry Mansion Inn
    From $377 per night (USD)

    Expedia

    Classic King, Pool - Curry Mansion Inn

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...

    From $377 per night (USD)

    Expedia

    Details
  • King Suite with Balcony - The James House
    From $389 per night (USD)

    VRBO

    King Suite with Balcony - The James House

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...

    From $389 per night (USD)

    VRBO

    Details
  • King Suite with Balcony - The James House
    From $385 per night (USD)

    Expedia

    King Suite with Balcony - The James House

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...

    From $385 per night (USD)

    Expedia

    Details
  • King Suite, Pet Friendly & Shared Pool
    From $364 per night (USD)

    VRBO

    King Suite, Pet Friendly & Shared Pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...

    From $364 per night (USD)

    VRBO

    Details
  • King Suite, Pet Friendly & Shared Pool
    From $369 per night (USD)

    Expedia

    King Suite, Pet Friendly & Shared Pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...

    From $369 per night (USD)

    Expedia

    Details
  • Classic King Balcony, Parking - The James House
    From $404 per night (USD)

    VRBO

    Classic King Balcony, Parking - The James House

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...

    From $404 per night (USD)

    VRBO

    Details
  • Classic Queen, Pet Friendly - Curry Mansion Inn
    From $346 per night (USD)

    Expedia

    Classic Queen, Pet Friendly - Curry Mansion Inn

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...

    From $346 per night (USD)

    Expedia

    Details
  • Classic King Balcony, Parking - The James House
    From $408 per night (USD)

    VRBO

    Classic King Balcony, Parking - The James House

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...

    From $408 per night (USD)

    VRBO

    Details
  • Classic Queen, Pet Friendly - Curry Mansion Inn
    From $347 per night (USD)

    Expedia

    Classic Queen, Pet Friendly - Curry Mansion Inn

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...

    From $347 per night (USD)

    Expedia

    Details
  • Classic King, Pool - Curry Mansion Inn
    From $377 per night (USD)

    VRBO

    Classic King, Pool - Curry Mansion Inn

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...

    From $377 per night (USD)

    VRBO

    Details
  • Classic King, Pool - Curry Mansion Inn
    From $377 per night (USD)

    Expedia

    Classic King, Pool - Curry Mansion Inn

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...

    From $377 per night (USD)

    Expedia

    Details
  • Deluxe King, Pet Friendly &  - Curry Mansion Inn
    From $374 per night (USD)

    VRBO

    Deluxe King, Pet Friendly & - Curry Mansion Inn

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...

    From $374 per night (USD)

    VRBO

    Details
  • Deluxe King with Balcony - The James House
    From $396 per night (USD)

    Expedia

    Deluxe King with Balcony - The James House

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...

    From $396 per night (USD)

    Expedia

    Details
  • Classic King, Pool - Curry Mansion Inn
    From $377 per night (USD)

    VRBO

    Classic King, Pool - Curry Mansion Inn

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...

    From $377 per night (USD)

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    Details
  • Deluxe Queen & Pet Friendly - Curry Mansion Inn
    From $384 per night (USD)

    Expedia

    Deluxe Queen & Pet Friendly - Curry Mansion Inn

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...

    From $384 per night (USD)

    Expedia

    Details
  • Deluxe Queen & Pet Friendly - Curry Mansion Inn
    From $385 per night (USD)

    VRBO

    Deluxe Queen & Pet Friendly - Curry Mansion Inn

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...

    From $385 per night (USD)

    VRBO

    Details
  • Deluxe Queen & Pet Friendly - Curry Mansion Inn
    From $299 per night (USD)

    Expedia

    Deluxe Queen & Pet Friendly - Curry Mansion Inn

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...

    From $299 per night (USD)

    Expedia

    Details
  • Deluxe Queen & Pet Friendly - Curry Mansion Inn
    From $299 per night (USD)

    VRBO

    Deluxe Queen & Pet Friendly - Curry Mansion Inn

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...

    From $299 per night (USD)

    VRBO

    Details
  • Southern snowbird-friendly house with pool, stunning backyard & great location
    From $2512 per night (USD)

    Expedia

    Southern snowbird-friendly house with pool, stunning backyard & great location

    Bedrooms:
    4
    Bathrooms:
    7
    Sleeps:
    10

    The Southernmost Comfort House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simpl ...

    From $2512 per night (USD)

    Expedia

    Details
  • King Suite with Balcony - The James House
    From $385 per night (USD)

    VRBO

    King Suite with Balcony - The James House

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...

    From $385 per night (USD)

    VRBO

    Details
  • Family Ready 1 BR Suite | Outdoor Pools | 4 Suites
    From $6452 per night (USD)

    VRBO

    Family Ready 1 BR Suite | Outdoor Pools | 4 Suites

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    16

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $6452 per night (USD)

    VRBO

    Details
  • Waterfront Room Retreat: Sparkling Pools | Three Spacious Rooms
    From $4848 per night (USD)

    VRBO

    Waterfront Room Retreat: Sparkling Pools | Three Spacious Rooms

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    12

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $4848 per night (USD)

    VRBO

    Details
  • Tropical Hideaway: Room in Resort - Steps from Key West's Vibrance | 2 Units
    From $1928 per night (USD)

    VRBO

    Tropical Hideaway: Room in Resort - Steps from Key West's Vibrance | 2 Units

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $1928 per night (USD)

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    Details
  • Beautiful ocean view condo
    From $660 per night (USD)

    VRBO

    Beautiful ocean view condo

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    A luxury, ocean front, 2 bedroom, (king in master, twins or twins as king in guest bedroom, queen sleeper in living room ...

    From $660 per night (USD)

    VRBO

    Details
  • A Palm Tree Haven in Key West
    From $1225 per night (USD)

    Expedia

    A Palm Tree Haven in Key West

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    8

    This lovely single-family, two-story luxury home is in the prestigious Truman Annex gated community on a very private cu ...

    From $1225 per night (USD)

    Expedia

    Details
  • Waterfront Resort w\/ Outdoor Pools | Spacious Room w\/ Scenic View
    From $1022 per night (USD)

    VRBO

    Waterfront Resort w\/ Outdoor Pools | Spacious Room w\/ Scenic View

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $1022 per night (USD)

    VRBO

    Details
  • Scenic Old Town Key West Retreat w\/ Pool Access
    From $911 per night (USD)

    VRBO

    Scenic Old Town Key West Retreat w\/ Pool Access

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $911 per night (USD)

    VRBO

    Details
  • Waterfront Stay in Duval St. Room w\/ Pool Access
    From $922 per night (USD)

    VRBO

    Waterfront Stay in Duval St. Room w\/ Pool Access

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $922 per night (USD)

    VRBO

    Details
  • Escape to Key West w\/ Exclusive Waterfront Stay & Pool Access | 4 Family Rooms
    From $3857 per night (USD)

    VRBO

    Escape to Key West w\/ Exclusive Waterfront Stay & Pool Access | 4 Family Rooms

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    16

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $3857 per night (USD)

    VRBO

    Details
  • Tropical Getaway! Refreshing Pools: 2 Blocks Away from Duval Street
    From $919 per night (USD)

    VRBO

    Tropical Getaway! Refreshing Pools: 2 Blocks Away from Duval Street

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $919 per night (USD)

    VRBO

    Details
  • Romantic Key West Getaway | Scenic Pool View Room
    From $973 per night (USD)

    VRBO

    Romantic Key West Getaway | Scenic Pool View Room

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $973 per night (USD)

    VRBO

    Details
  • Harbor Oasis Room: Tranquil Seaport & Water Fun
    From $1258 per night (USD)

    VRBO

    Harbor Oasis Room: Tranquil Seaport & Water Fun

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $1258 per night (USD)

    VRBO

    Details
  • Perfect Key West Escape! Scenic Harbor View Room Ideal for Romantic Stay
    From $1188 per night (USD)

    VRBO

    Perfect Key West Escape! Scenic Harbor View Room Ideal for Romantic Stay

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $1188 per night (USD)

    VRBO

    Details
  • Relaxing Room w\/ Water View | Pool Access
    From $1081 per night (USD)

    VRBO

    Relaxing Room w\/ Water View | Pool Access

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $1081 per night (USD)

    VRBO

    Details
  • Hyatt Residence Club, Sunset Harbor - Beautiful Location
    Click For Pricing

    Expedia

    Hyatt Residence Club, Sunset Harbor - Beautiful Location

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    In the heart of Old Town, perfectly situated on the western side of the island, this gracious retreat overlooks the Gulf ...

    Click For Pricing

    Expedia

    Details
  • Your Private Key West Escape | 3 Family Ready Room, Near Duval Street Nightlife
    From $2892 per night (USD)

    VRBO

    Your Private Key West Escape | 3 Family Ready Room, Near Duval Street Nightlife

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    12

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $2892 per night (USD)

    VRBO

    Details
  • Idyllic Key West Room w\/ Poolside Bar & Watersports | 2 Family Rooms
    From $3192 per night (USD)

    VRBO

    Idyllic Key West Room w\/ Poolside Bar & Watersports | 2 Family Rooms

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $3192 per night (USD)

    VRBO

    Details
  • Key West Room Retreat | Two Family Ready Suites Perfect For Long Stays
    From $3017 per night (USD)

    VRBO

    Key West Room Retreat | Two Family Ready Suites Perfect For Long Stays

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $3017 per night (USD)

    VRBO

    Details
  • Perfect Location to Key West Action! Pool and Garden View Room w\/ Balcony
    From $931 per night (USD)

    VRBO

    Perfect Location to Key West Action! Pool and Garden View Room w\/ Balcony

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $931 per night (USD)

    VRBO

    Details
  • Tropical Escape! 2 Spacious Rooms w\/ Balcony
    From $1822 per night (USD)

    VRBO

    Tropical Escape! 2 Spacious Rooms w\/ Balcony

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $1822 per night (USD)

    VRBO

    Details
  • Relaxing Room w\/ Balcony & Breathtaking View
    From $986 per night (USD)

    VRBO

    Relaxing Room w\/ Balcony & Breathtaking View

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $986 per night (USD)

    VRBO

    Details
  • Spacious Suite w\/ Terrace & Scenic Harbor View
    From $1479 per night (USD)

    VRBO

    Spacious Suite w\/ Terrace & Scenic Harbor View

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $1479 per night (USD)

    VRBO

    Details
  • Best Spot Near Duval Street Nightlife! Suite ScenicHarbor View and Terrace
    From $1396 per night (USD)

    VRBO

    Best Spot Near Duval Street Nightlife! Suite ScenicHarbor View and Terrace

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $1396 per night (USD)

    VRBO

    Details
  • Your Waterfront Hideaway in the Heart of Key West
    From $1760 per night (USD)

    VRBO

    Your Waterfront Hideaway in the Heart of Key West

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $1760 per night (USD)

    VRBO

    Details
  • Breathtaking Waterfront Retreat | Spacious 1BR Suite w\/ Living Area
    From $1509 per night (USD)

    VRBO

    Breathtaking Waterfront Retreat | Spacious 1BR Suite w\/ Living Area

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $1509 per night (USD)

    VRBO

    Details
  • Chic Waterfront Room | 1BR Suite w\/ Balcony | Outdoor Pools
    From $1666 per night (USD)

    VRBO

    Chic Waterfront Room | 1BR Suite w\/ Balcony | Outdoor Pools

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $1666 per night (USD)

    VRBO

    Details
  • Harbor front Hideaway w\/ Pools & Seaside Dining | 1BR Spacious Suite
    From $1595 per night (USD)

    VRBO

    Harbor front Hideaway w\/ Pools & Seaside Dining | 1BR Spacious Suite

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $1595 per night (USD)

    VRBO

    Details
  • Old Town Key West Cottage 3bed\/2bath
    From $511 per night (USD)

    VRBO

    Old Town Key West Cottage 3bed\/2bath

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Fully furnished ground floor cottage with 3 bedrooms (queen bed in every bedroom), 2 full bathrooms, plus a loft with an ...

    From $511 per night (USD)

    VRBO

    Details
  • 4 Family Ready Suites | Spacious and Near Duval Street Nightlife
    From $6102 per night (USD)

    VRBO

    4 Family Ready Suites | Spacious and Near Duval Street Nightlife

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    16

    Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...

    From $6102 per night (USD)

    VRBO

    Details
  • Best Location -Hyatt Sunset Harbor- water view-Jan 26 to Feb 2.  Seven nights
    From $759 per night (USD)

    VRBO

    Best Location -Hyatt Sunset Harbor- water view-Jan 26 to Feb 2. Seven nights

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    LISTING is ONLY available January 26 to Feb 2. Best location in town. Only 1.5 blocks to Duvall Street but quiet. Key We ...

    From $759 per night (USD)

    VRBO

    Details
  • Studio Near Downtown - The Bartlum
    From $561 per night (USD)

    Expedia

    Studio Near Downtown - The Bartlum

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: Welcome to the Bartlum, a historic and luxurious studio apartment just steps to Duval Street. This studio, lo ...

    From $561 per night (USD)

    Expedia

    Details