Long considered a sign of hospitality, the pineapple is widely recognized as sign of Welcome and Friendship, and so we welcome YOU to the Perfect Pineapple!
All Units On Special
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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.
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
This cozy and charming vacation rental in Truman Annex is guaranteed to make you feel right at home.
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
Here is your perfect opportunity to stay in one of the most popular complexes of Key West, the Truman Annex!
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
Located in the historic Bahama Village neighborhood, nestled amongst the palms, you‘ll find the stately building that houses Treetop Paradise.
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.
Just steps away from Harry Truman's "Little White House" you’ll find your vacation dreams come true!
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
Built in 1889 with original Dade County Pine, history comes alive when you enter this luxurious private home.
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
Lounge your days away by the pool or enjoy the peace and quiet away from the hustle and bustle of Duval Street.