The Shipyard vacation rentals

We found 151 vacation rentals — enter your dates for availability

Embrace the enchanting allure of Key West, where historic charm meets breathtaking sunsets over crystal-clear waters. Stroll through the vibrant streets of Old Town, savoring local cuisine and vibrant nightlife on Duval Street, or explore the rich history at the Ernest Hemingway Home and Museum. With a variety of accommodations—from cozy condos to spacious homes—traveling with family or friends becomes a breeze, ensuring a comfortable and memorable escape in this tropical paradise. Experience the warmth of a vacation rental, where you'll find space, amenities, and a home-like atmosphere that invites relaxation and adventure.

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more
  • More for less

    More space, more privacy, more amenities — more value
  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
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