Key West Luxury Rentals

We selected the 124 homes worth renting in this location

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Home spotlights in Key West

Dockside Dreams

Dockside Dreams

  • 10 guests

  • 4 bedrooms

Key Haven, Key West

Tucked along the water’s edge in a peaceful gated community, this four-bedroom Key West retreat is made for laid-back days and warm, breezy nights. With a private heated pool, a gated garden, and a dock for boats up to 50 feet, it’s an ideal home for family and friend getaways.

Key West Retreat

Key West Retreat

  • 12 guests

  • 4 bedrooms

Key Haven, Key West

This spacious and stylish waterfront home offers the perfect setting for a relaxing Key West getaway. The bright, open-concept layout is ideal for family gatherings or entertaining friends.

A Quiet Realm

A Quiet Realm

  • 11 guests

  • 4 bedrooms

Birch Park Finger Streets, Fort Lauderdale

Set just a block from the Atlantic Ocean on an impressively-sized lot, this villa is bucket-list worthy without a doubt. A home cinema, heated outdoor pool, jacuzzi, direct beach access, kayaks – these are just some of the reasons it caught our attention.

Summer Serenade

Summer Serenade

  • 14 guests

  • 7 bedrooms

Harbour Inlet, Fort Lauderdale

Experience the ultimate coastal lifestyle at Grace Harbor, a stunning waterfront retreat in Fort Lauderdale's prestigious Harbor Beach neighbourhood. Minutes from the local bars and restaurants, the home sits on the waterfront (with space to dock a 25ft boat) within walking distance of the largest beach in Fort Lauderdale.


We selected the top 3% holiday homes in Key West Luxury Rentals

Explore the 124 most perfect homes in our collection

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Most popular homes in Key West

Sunstone Villa

Sunstone Villa

  • 16 guests

  • 5 bedrooms

Biscayne Gardens, Florida

Lake & Light

Lake & Light

  • 16 guests

  • 6 bedrooms

Ojus, Miami-Dade County

Orchid White

Orchid White

  • 16 guests

  • 7 bedrooms

Parker Ridge, West Palm Beach

Paradise Key

Paradise Key

  • 14 guests

  • 6 bedrooms

Key Haven, Key West

Family Fortress

Family Fortress

  • 12 guests

  • 4 bedrooms

Victoria Park, Fort Lauderdale

The Waterways

The Waterways

  • 10 guests

  • 5 bedrooms

Hollywood Lakes, Hollywood

Sunlit Shores

Sunlit Shores

  • 15 guests

  • 5 bedrooms

Ojus, Miami-Dade County

Ocean's Gem

Ocean's Gem

  • 16 guests

  • 5 bedrooms

Ojus, Miami-Dade County

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A handpicked selection of the best luxury homes in Key West, Monroe County, Florida, United States, as chosen by the experts who've visited and vetted thousands of the city's homes. Luxurious interiors, sumptuous bedrooms and prime city centre locations. Available for short and extended stays.

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