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.
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Find the best place to stay - The Shipyard
Truman Annex Best Location in Town
Sleeps 4 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
54 reviews(54 reviews)
Boli Townhouse - Luxury WEEKLY Rental in gated Truman Annex-Saturday to Saturday
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
193 reviews(193 reviews)
Cocktails & Dreams: Modern 2nd Floor Condo, Steps from Duval St, Seaport, Waterpark, Beach & Pool!
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
19 reviews(19 reviews)
Key West Oasis, Don't wait- book your dream stay now.
Sleeps 6 · 2 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
210 reviews(210 reviews)
Key West Hen
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
189 reviews(189 reviews)
Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach
Sleeps 6 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
144 reviews(144 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value
