The Shipyard holiday rentals
We found 151 holiday rentals — enter your dates for availability
Find spaces that suit your style
House
Condo/Apartment
Find the best place to stay - The Shipyard
Sand Crab Cabana WEEKLY RENTAL 7 nights minimum!! Truman Annex
Sleeps 2 · 1 bedroom · 1 bathroom
excellent
(50 reviews)
Top rated rentals - The Shipyard
Loved Location, Acomodations & Grounds/Pool
exceptional
(5 reviews)
We're long time visitors and stayed for nine nights, it met all our expectations as did the property managers (Compass Realty). We'll definitely be returning guests!
Michael P.
Stayed Apr 2025
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
More holiday ideas
- Downtown Key West Holiday Rentals
- Ernest Hemingway Home and Museum Holiday Rentals
- Pelican Landing Holiday Rentals
- Stock Island Holiday Rentals
- Truman Annex Holiday Rentals
- Key West Historic District Holiday Rentals
- Key West Holiday Rentals
- Key West Beach Club Holiday Rentals
- Cottage rentals in Key West
- Houseboat rentals in Key West