Old Town
Cozy apartment within biking distance to The Historic Seaport, Cuban Coffee Queen, local grocery store Fausto's and even Higgs Beach.
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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 1 - 12 of 18 results matching your search criteria
Map ViewStock Island
Located on the main road meandering through the secluded gated Key West Golf Club community, you’ll find A Little Slice of Paradise. Spend a month (or two) in this charming townhouse and you may never return home.
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
Enjoy your private front porch in this quiet neighborhood in Old Town Key West. Located in The Colony compound, Ibis is a wonderful one bedroom one bath Key West rental home with a shared pool on property.
Old Town
A quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking.
Old Town
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.
Stock 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.
Mid Town
Meander down a quiet street in midtown Key West until you come upon a white picket fence on a shady corner lot. Park and walk around to open the gate.
Old Town
Built in 1889 with original Dade County Pine, history comes alive when you enter this luxurious private home.
Mid Town
Bask in complete privacy in this Key West tropical paradise with a lagoon style pool. This property is pet friendly.
Old Town
Do not look any further! Your perfect vacation home rental is right here! Offering a private pool with lounge chairs and covered outside porch. You can also bring your Fido!
Old Town
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!