Key West Luxury Homes

Award-winning homes from £98

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Home spotlights in Key West

 Shellstone Magic

Shellstone Magic

  • 16 guests

  • 8 bedrooms

Key Haven, Key West

This modern coastal retreat is all about laid-back luxury and sun-soaked living. With an ultra-sleek design, spacious interiors, and a private pool, it’s made for unwinding in style.

Dream Escape

Dream Escape

  • 14 guests

  • 6 bedrooms

Key Haven, Key West

Step off the dock and straight into holiday mode — this waterfront retreat is made for easygoing island days. Set in a gated community with its own private marina, you can moor your boat just steps from the door.

Views In The Making

Views In The Making

  • 17 guests

  • 7 bedrooms

Cloud Lake, Palm Beach County

This stunning 2 side-by-side homes on the lake offer guests plenty of space to soak up the sun, with a total of 2,940 square feet of luxury living. The open-plan living room is perfect for spending quality time with friends and family, and the bedrooms are all outfitted with fresh linens, plump pillows, and ultra-comfy mattresses.

Golden Acres

Golden Acres

  • 8 guests

  • 3 bedrooms

Rural Estates, Collier County

This supped-up villa, located just minutes from the pristine beaches of Southwest Florida, is tailor-made for a multi-generational family stay. Think an enclosed heated swimming pool, Jacuzzi, and an impressive covered terrace with an outdoor grill set-up for easy meal times.


We selected the top 3% holiday homes in Key West Homes

Explore the 672 most perfect homes in our collection

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Most popular homes in Key West

Sunshine With a View

Sunshine With a View

  • 11 guests

  • 4 bedrooms

Harbour Inlet, Fort Lauderdale

Endless Ocean

Endless Ocean

  • 8 guests

  • 4 bedrooms

Birch Park Finger Streets, Fort Lauderdale

Dockside Dreams

Dockside Dreams

  • 10 guests

  • 4 bedrooms

Key Haven, Key West

Tranquil Bay

Tranquil Bay

  • 12 guests

  • 4 bedrooms

Key Haven, Key West

Naples Aglow

Naples Aglow

  • 8 guests

  • 4 bedrooms

Old Naples, Naples

Palm to Palm

Palm to Palm

  • 8 guests

  • 4 bedrooms

Northwood Shores, West Palm Beach

A Drop of Sunlight

A Drop of Sunlight

  • 18 guests

  • 7 bedrooms

Nurmi Isles, Fort Lauderdale

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Frequently asked questions

Similar destinations

All Plum Guide homes in Key West, Monroe County, Florida, United States have been tested and approved by our team of independent home critics. These meticulous beings inspect everything –from the convenience of each house’s location right down to the art on the walls– so what you see really is what you get. Worried about thin curtains? Accessibility? Maybe wifi speed is your biggest concern? Rest assured, we obsessively check each home in Key West, Monroe County, Florida, United States before approving it, so you can book with peace of mind.

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