Vacation Rentals & House Rentals in Key West

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Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Pool or snooker table

All filters match

Price per night from

$623

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Pool or snooker table

All filters match

Price per night from

$654

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Pool or snooker table

All filters match

Price per night from

$523

These homes match some but not all of your filters. Clear all filters

Lovely 2 bedroom, 2 bath condo at La Brisa.

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, 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: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$402

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: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$339

1 of 2 match: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$860

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

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$344

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

Key West apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$841

BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$135

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: Pool or snooker table, 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: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,949

Coconut Mallory Resort and Marina

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$347

Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$860

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: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$746

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Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$975

Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,147

Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$860

Leaward Isle close to the Ocean' & a short bike downtown. Best value at 1800

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$860

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: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$860

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: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,376

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: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,434

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,147

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: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$479

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$860

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$382

Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$975

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$172

Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$860

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: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$574

Ocean Front Key West Oasis Island Tones Charming Historical Downtown area

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$765

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: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,720

“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: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$797

Hyatt Sunset Harbor

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$497

Hyatt Sunset Harbor

Stock Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$445

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$912

1 of 2 match: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$912

Hyatt Beach House! Quiet Key West Location!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$472

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