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Helen's Hideaway

2 Bedrooms
2 Bathrooms
(55 Reviews)
This gem is located at the end of a hidden lane, just off Simonton Street, behind The Gardens Hotel. Helen's Hideaway is a step back in time to Key West during its slumbering past. Built by David Wolkowski, who built many of Key West's premier resorts, including the Pier House, this paradise...

Flagler's Crossing

2 Bedrooms
2 Bathrooms
Flagler's Crossing is a stunning 3 story condo with 2 bedrooms and 2 1/2 bathrooms. This home is one of the very few in Key West with a backyard ocean view! There is off-street covered parking, boat dockage, shared pool, multiple balconies, and an outdoor living area.

The backyard haven includes a...

Seaport Suite

4 Bedrooms
3 Bathrooms
(34 Reviews)
Seaport Suite is available for daily vacation rentals and located on the second floor of an historic Key West home in Old Town.. The location is as close to perfect as you can get, being one block off Duval Street and within walking distance to every single thing you could possibly want to do. With...

Kingfish Keep On Duval

1 Bedroom
1 Bathroom
(9 Reviews)
This large and luxurious apartment is second to none when it comes to properties on Duval St. Walking distance to Southernmost Point, Mallory Square, beaches, restaurants, and bars, you cant beat the location. No detail was overlooked in the design of this property. There are vaulted ceilings,...

Papa's Hideaway #1 - Torrents of Spring

1 Bathroom
(51 Reviews)
Papa's Hideaway was a historic Key West Inn with all the charm of Hemingway's day and the convenience of being just one block off Duval street. The perfect mix of location, atmosphere and value.

Feel your tensions release as you soak up the warm tropical sun. Listen to the trade winds rustling...