Vacation Rentals & House Rentals in Key West

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NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Shared outdoor pool (unheated) Freezer

All filters match

Price per night from

$1,946

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

Match: Shared outdoor pool (unheated) Freezer

All filters match

Price per night from

$338

Match: Shared outdoor pool (unheated) Freezer

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Price per night from

$911

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Freezer

All filters match

Price per night from

$911

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

Match: Shared outdoor pool (unheated) Freezer

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Price per night from

$107

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

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Shared outdoor pool (unheated) Freezer

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Price per night from

$344

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Lovely 2 bedroom, 2 bath condo at La Brisa.

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$161

Island Suite @ KW Vacation

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$401

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

1 of 2 filters match

Price per night from

$859

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

Key West apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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

1 of 2 filters match

Price per night from

$840

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$859

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$382

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

Key West apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$573

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$1,374

“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: Freezer, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$796

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

Key West apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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

1 of 2 filters match

Price per night from

$1,718

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$1,432

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$745

Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$974

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$1,145

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$859

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Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$974

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$478

Ocean Front Key West Oasis Island Tones Charming Historical Downtown area

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$764

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$172

Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$1,145

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$859

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$1,374

Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$1,374

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$974

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$859

Botanical Island Delight Key West fantastic discounts for Summer & Fall

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$745

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$859

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$859

Southernmost Beauty

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

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

1 of 2 filters match

Price per night from

$267

Historic Carriage House

Key West cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

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

1 of 2 filters match

Price per night from

$229

Clean Apartment in Old Town Key West (Best Downtown Locations)

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 46 minutes

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

1 of 2 filters match

Price per night from

$384

Key West Suites Hotel unit 201

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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

1 of 2 filters match

Price per night from

$1,145

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rentals in Key West

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