Vacation Rentals & House Rentals in Key West

Updating...

age 0-16
50 Results

Relevance

Price: low to high

Price: high to low

Reviews

50 house rentals

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Table tennis

All filters match

Price per night from

$622

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Table tennis

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) Table tennis

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: Table tennis, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$160

Island Suite @ KW Vacation

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$400

Entire House with Deep Water Dock & Heated Pool - 4 Min. to KW - Pets OK

Stock Island house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

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

1 of 2 filters match

Price per night from

$797

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: Table tennis, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$337

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

1 of 2 filters match

Price per night from

$343

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: Table tennis, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$134

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

Key West apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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

1 of 2 filters match

Price per night from

$106

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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

1 of 2 filters match

Price per night from

$1,939

Hyatt Sunset Harbor

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$510

Hyatt Sunset Harbor

Stock Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$523

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: Table tennis, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$859

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$172

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$1,145

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: Table tennis, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$859

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: Table tennis, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$478

Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$974

Ocean Front Key West Oasis Island Tones Charming Historical Downtown area

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$764

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: Table tennis, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,374

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: Table tennis, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$745

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$382

Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$1,145

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: Table tennis, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$859

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: Table tennis, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,718

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$859

Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$859

<

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$974

“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: Table tennis, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$796

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: Table tennis, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,432

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: Table tennis, 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: Table tennis, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$573

Coconut Mallory Resort and Marina

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$346

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$907

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

1 of 2 filters match

Price per night from

$907

Viewing 38 of 50
rentals in Key West

×

Also consider