Vacation Rentals & House Rentals in Key West

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47 house rentals

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Match: Shared outdoor pool (unheated) Staffed property

All filters match

Price per night from

$912

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Staffed property

All filters match

Price per night from

$912

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: Staffed property, 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: Staffed property, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$402

Luxury Condominium in Old Town | Monthly Rental at Steamplant Key West

Key West condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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

1 of 2 filters match

Price per night from

$316

SEAPORT SAILING—Beach-Pool-BBQ-55”TV-HotTub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$975

Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach

Key West townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$917

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: Staffed property, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$339

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

1 of 2 filters match

Price per night from

$859

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

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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

1 of 2 filters match

Price per night from

$840

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: Staffed property, 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: Staffed property, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,949

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: Staffed property, 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: Staffed property, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$796

Ocean Front Key West Oasis Island Tones Charming Historical Downtown area

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$764

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$859

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: Staffed property, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$573

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$382

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$859

Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$974

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: Staffed property, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,718

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: Staffed property, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$745

Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$1,145

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: Staffed property, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,432

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$172

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: Staffed property, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$478

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Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$974

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: Staffed property, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$859

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: Staffed property, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$974

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: Staffed property, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$859

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: Staffed property, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$859

Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$1,374

Botanical Island Delight Key West fantastic discounts for Summer & Fall

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$745

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: Staffed property, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,374

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: Staffed property, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$859

Great rentals within 20 miles that match your search

Hyatt Sunset Harbor

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Staffed property

All filters match

Price per night from

$497

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rentals in Key West

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