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Irish in Truman Annex Shipyard close to Historic Duval & Ft Zach State Park

Key West apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Rental types Shared outdoor pool (unheated)

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Price per night from

$574

Atlantic Paradise Found modern luxury Best pool in Key West fine finishes

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (unheated)

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Price per night from

$1,377

Botanical Island Delight Key West fantastic discounts for Summer & Fall

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Rental types Shared outdoor pool (unheated)

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Price per night from

$746

Key West Affordable Ocean View Condo. Clean priced well on the Atlantic

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (unheated)

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Price per night from

$746

Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (unheated)

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Price per night from

$1,377

Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (unheated)

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Price per night from

$1,148

Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (unheated)

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Price per night from

$976

Tropical Paradise Key West - Upgraded Master Bath - Best Value Discounts

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (unheated)

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Price per night from

$861

Ocean Front Key West Oasis Island Tones Charming Historical Downtown area

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (unheated)

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Price per night from

$766

Salty Sea Breezes, Exquisite Morning Sunrises, Luxurious Condo. Fall Specials

Key West apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Shared outdoor pool (unheated)

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Price per night from

$841

Ocean View Monthly Rental at 1800 Atlantic- Open Nov, December & January

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Rental types Shared outdoor pool (unheated)

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Price per night from

$172

Atlantic Ocean Breezes, Tropical Island Sunrises, Downtown 10 minutes away

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (unheated)

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Price per night from

$382

Casa Coastal East, Morning sunrises, Evening night time vibes An Island home.

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Rental types Shared outdoor pool (unheated)

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Price per night from

$479

Somewhere on the Beach a dream property all amenities included simply amazing

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (unheated)

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Price per night from

$1,434

Key Wes't Best- Upgraded condo 5 mins to Smathers Beach Fantastic value

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (unheated)

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Price per night from

$1,377

High Tide awaits your next visit upgraded condo close to Smathers Beach

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (unheated)

All filters match

Price per night from

$861

Our Nautical Home in Key West is available for amazing prices Summer of 2023

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (unheated)

All filters match

Price per night from

$861

Mar Y Sol a spectacular Ocean Front Oasis 10 minutes to Historic District

Key West apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Shared outdoor pool (unheated)

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Price per night from

$1,721

Frost Free at 1800 Atlantic overlooking Smathers Beach top floor & upgrades

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (unheated)

All filters match

Price per night from

$1,148

Key West On My Mind, Ocean Views, Renovated Kitchen, Last minute deals

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (unheated)

All filters match

Price per night from

$861

Top floor Ocean Views, Spacious 2 Bedroom Condo, Views from every room

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (unheated)

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Price per night from

$976

Poolside Breeze a Tropical Retreat has a wrap around Balcony best location

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (unheated)

All filters match

Price per night from

$861

Paradise Found in Key West upgrades throughout 5 minutes to Smathers Beach

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (unheated)

All filters match

Price per night from

$861

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Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (unheated)

All filters match

Price per night from

$976

Lovely 2 bedroom, 2 bath condo at La Brisa.

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (unheated)

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Price per night from

$161

Island Suite @ KW Vacation

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Rental types Shared outdoor pool (unheated)

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Price per night from

$402

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One-bedroom time share suite in the heart of Old Key West

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 26 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$339

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$861

Cozy Key West Hideaway with a Pool, Digital Workspace, and Privacy

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$345

Seaside Condo 2 pools. sunny, quiet, near Old Town

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 48 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$107

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,950

“The perfect place to stay in Key West” This property is just 1 block off Duval -- but closer to the quiet, quaint side. I was so impressed with the accomodations -- fully equipped! We could have stayed there a month! The grounds are beautiful, lush, tropical and quiet. Staff was super friendly -- it is also very private with a large locking wrought iron gate keeping the units apart from the street -- we loved everything about it! We will stay here again on our next visit for sure!~

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$798

SEAPORT SERENITY in Old Town—Beach-Pool-BBQ-Hot Tub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$912

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$912

2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“We'll be back...” We found this condo to be very clean and comfortable. We enjoyed sitting at the pool as well. Paul, the caretaker, was very pleasant and most accommodating. We shared the condo with another couple for our two night stay. It was wonderful to have our privacy (2 BR/2 baths) but still be able to share the kitchen/living room area with our friends. We had a rental car so found the location easy for shopping, dining, sightseeing on other keys and, of course, Duval Street.

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$488

Conch Haven Cottage Old Town Studio MONTHLY Rental

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$108

Henry's Piece Of Paradise On The Ocean In Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“nice place” Accommodations were nice Good view Henry was great to work with

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$465

Artist Cottage

Key West apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Key West, Spring 2012” In a word,our stay with you was ”wonderful”. We have been to Key West on several occasions and have loved every visit. Staying in Truman annexe was even more special. We all felt like we were at home with everything we needed. You must feel blessed to live in that part of the world. We will be looking for a job for our 19 year old son,Tom. He wants to come and work over in Key West. We have just arrived home and everything seems grey, and much colder than Key West. Depending on finances( the pound-dollar rate is not too good just now) we hope to come back soon. We will definitely be giving you a call.I would recommend your accommodation and company to future holiday makers. Love and blessings John,Jayne,Jack and Tom

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$380

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rentals in Key West

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