Vacation Rentals & House Rentals in Key West

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28 house rentals

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available 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: Boat available 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: Boat available Table tennis

All filters match

Price per night from

$523

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

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: Boat available, Table tennis

1 of 2 filters match

Price per night from

$801

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Table tennis, Boat available

1 of 2 filters match

Price per night from

$1,950

80' luxury yacht

Stock Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Boat available

1 of 2 filters match

Price per night from

$4,016

“Fantastic Stay!” My husband and two sons (21 & 24) stayed in this condo over Christmas. This was our first stay in Key West and we wanted to be close to everything, but yet not right on Duval St. This location was perfect; literally a stones throw away from Duval St. The unit inside was decorated very lovely and had all the amenities one would need. I found the owners were nice to do business with, especially Deb who I mostly communicated with. My family and I enjoyed our stay in Key West immensely, we had so much fun! We met many very friendly people out and about town. We would love to visit again, if we do, we would like to stay in this condo or the Bella Vita, the owner's other condo.

Responds fast! avg. 14 minutes

1 of 2 match: Table tennis, Boat available

1 of 2 filters match

Price per night from

$287

1 of 2 match: Table tennis, Boat available

1 of 2 filters match

Price per night from

$263

Hyatt Sunset Harbor

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Boat available

1 of 2 filters match

Price per night from

$496

Hyatt Sunset Harbor

Stock Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Table tennis, Boat available

1 of 2 filters match

Price per night from

$445

Coconut Mallory Resort and Marina

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Boat available

1 of 2 filters match

Price per night from

$346

Best Downtown Location Monthly Rental Open Nov 2023- Jan 2024

Key West apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Table tennis, Boat available

1 of 2 filters match

Price per night from

$382

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, Boat available

1 of 2 filters match

Price per night from

$859

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, Boat available

1 of 2 filters match

Price per night from

$859

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, Boat available

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, Boat available

1 of 2 filters match

Price per night from

$1,718

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, Boat available

1 of 2 filters match

Price per night from

$478

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, Boat available

1 of 2 filters match

Price per night from

$912

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: Table tennis, Boat available

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: Table tennis, Boat available

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: Table tennis, Boat available

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: Table tennis, Boat available

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: Table tennis, Boat available

1 of 2 filters match

Price per night from

$745

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: Table tennis, Boat available

1 of 2 filters match

Price per night from

$859

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Boat available

1 of 2 filters match

Price per night from

$525

Hyatt Beach House! Quiet Key West Location!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Boat available

1 of 2 filters match

Price per night from

$471

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Boat available

1 of 2 filters match

Price per night from

$525

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Boat available

1 of 2 filters match

Price per night from

$484

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