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.
Searching for an affordable monthly vacation rental in the heart of Key West? Do you plan on spending most of your time enjoying all that Key West has to offer and seeing what if feels like to really live like a local? Then tune into Windchime!
When a name says it all you know you have made the perfect choice for your Key West island escape.
This great 2 bedroom, 2 bathroom, Key West condo located at 1800 Atlantic Condominiums offers you a wonderful relaxing garden view overlooking the nature preserve.
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
Welcome to your home away from home in Key West. This lovely town home is located in the Key West Golf Club Community, and allows you to enjoy all that Key West has to offer while staying in a relaxing environment.
Key Lime Pie is a private cottage that perfectly encompasses the “Key West vibe” that you’re looking for. The minute you walk in to see the bright, sunny walls and local artwork, you know you are somewhere special.
Tumi’s Time Out is a 2-bedroom, 2-bathroom town-home in the sought after Windward Park community. A secluded compound that is a tropical hideaway, surrounded by lush palms and balmy breezes.
Enjoy spectacular ocean views from this lovely rental!
Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE!
Just steps away from Harry Truman's "Little White House" you’ll find your vacation dreams come true!
Step into a tranquil community on a quiet lane and discover the Boat House, a nautically themed treasure in Old Town Key West.
“Amazingly Perfect!” That is how one of our delighted guests reviewed Southard Getaway and we’re sure you’ll agree. Imagine arriving in Key West to this beach-like home within walking distance of all that Key West has to offer.
