Old Town
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.
All Units On Special
You are here
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 13 - 24 of 72 results matching your search criteria
Map ViewStock Island
Coral Palm is a lovely 3 bedroom, 3 bathroom, 2 story town home located in the private gated community of Coral Hammock on Stock Island.
Old Town
“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.
Old Town
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
Mid Town
Bask in complete privacy in this Key West tropical paradise with a lagoon style pool. This property is pet friendly.
Old Town
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
Ocean Side
Imagine swimming in the Olympic sized pool and enjoying a spectacular view of the Atlantic Ocean at the same time. How about an evening stroll through the tropical jungle in your own backyard.
Old Town
Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE!
Old Town
Located in Bahama Village, a quaint neighborhood in Old Town Key West, this beautifully renovated conch home is a romantic island getaway. This rental is a guest house situated in the back yard of a private residence.
Old Town
Cozy apartment within biking distance to The Historic Seaport, Cuban Coffee Queen, local grocery store Fausto's and even Higgs Beach.
Stock Island
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.
Old Town
Twice the comfort, twice the amenities, that’s The Dolphin House, located in the exclusive Truman Annex community in the heart of Old Town.