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All of the rentals below have at least one available deal or discount, which can vary depending on when you book or when you plan to take your trip. Just click on the Explore All Specials button next to each listing to see the terms of the available deals. Searching your stay dates will show you all properties that have an available deal during that time. You can also view all of our current promotions and see the details of each one on our main Deals page.

Displaying 25 - 36 of 72 results matching your search criteria
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Mid Town

Bask in complete privacy in this Key West tropical paradise with a lagoon style pool. This property is pet friendly.

Old Town

Step into a tranquil community on a quiet lane and discover the Boat House, a nautically themed treasure in Old Town Key West.

Old Town

Located in one of Key West’s historic and most cultural neighborhoods this lovely condominium will give you cause to celebrate the island way of life.

Old Town

**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.

Old Town

Located in the historic Bahama Village neighborhood, nestled amongst the palms, you‘ll find the stately building that houses Treetop Paradise.

Old Town

The location of La Casita cannot be beat -- right in the heart of Old Town yet on a quiet lane, only steps to Duval Street. This property is a monthly rental only. Sleeps 4 people.

Stock Island

Coral Garden is a two bedroom town home in the quiet gated community of Coral Hammock located on Stock Island. Perfect for families or those who are working from home. Close to all that Key West has to offer.

Old Town

Location! Location! Location! Duval Breeze offers the best location in town! Walking distance to restaurants, bars and galleries and easy biking distance to the beaches!

Old Town

Lounge your days away by the pool or enjoy the peace and quiet away from the hustle and bustle of Duval Street.

Old Town

Situated on Key West's historical Whitehead Street is Spanish Lime Cottage, appropriately named for one of the lime trees in the back yard. Whitehead runs parallel to Duval Street and is right in the heart of Old Town, Key West.

Old Town

Your perfect escape to Key West awaits you in the Land of Love.

Old Town

Make your next Florida vacation something special with this charming home in a quiet, upscale enclave that is close to everything!

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