Luxury Long Stay Rentals in Key West

We selected the 540 homes worth renting in this location

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Home spotlights in Key West

Island Sophisticate

Island Sophisticate

  • 16 guests

  • 6 bedrooms

Key Haven, Key West

This impeccably decorated home is a masterclass in island elegance, where every detail has been thoughtfully designed for comfort and style. It's light-filled, spacious, and beautifully finished with a refined, coastal touch.

A Drop of Sunlight

A Drop of Sunlight

  • 18 guests

  • 7 bedrooms

Nurmi Isles, Fort Lauderdale

Discover a different side of Florida when you visit this bright and modern villa in the Nurmi Isles of Fort Lauderdale. Not known as the Venice of America for nothing, a network of canals surrounds the neighbourhood, giving way to a beautiful view from the firepit and the private swimming pool.

The Pearl of Key West

The Pearl of Key West

  • 16 guests

  • 6 bedrooms

Key Haven, Key West

Spend your days soaking up the island breeze at this laid-back retreat just outside Key West. Tucked inside a quiet gated community, this spacious six-bedroom home is made for group getaways, with a private boat slip, breezy balconies, and enough room for everyone to spread out.

Paradise Key

Paradise Key

  • 14 guests

  • 6 bedrooms

Key Haven, Key West

Discover the magic of Florida from this impressive home in Key West. Outside, you can relax and unwind by the private heated pool.


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

Explore the 540 most perfect homes in our collection

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Most popular homes in Key West

Six Leaves Left

Six Leaves Left

  • 4 guests

  • 2 bedrooms

South Middle River, Fort Lauderdale

Bergamot & Sunshine

Bergamot & Sunshine

  • 6 guests

  • 2 bedrooms

Hollywood South Central Beach, Hollywood

Keys to Paradise

Keys to Paradise

  • 14 guests

  • 6 bedrooms

Key Haven, Key West

 Marina Living

Marina Living

  • 18 guests

  • 8 bedrooms

Key Haven, Key West

Tranquil Bay

Tranquil Bay

  • 12 guests

  • 4 bedrooms

Key Haven, Key West

Dockside Dreams

Dockside Dreams

  • 10 guests

  • 4 bedrooms

Key Haven, Key West

Chasing the Waves

Chasing the Waves

  • 6 guests

  • 2 bedrooms

Hollywood South Central Beach, Hollywood

The Sultan

The Sultan

  • 2 guests

  • 1 bedrooms

Parker Ridge, West Palm Beach

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Check upcoming rates & availability for Key West Long Stay Rentals


Frequently asked questions

Similar destinations

Explore our collection of luxury Extended Stay Rentals available for you to rent in Key West, Monroe County, Florida, United States. Each and every home you'll find has been through a meticulous, multi-stage vetting process to ensure quality our guests can always count on. The Long Stay Rentals in our Key West, Monroe County, Florida, United States collection come fully furnished with well-equipped kitchens, all linens, and essential bathroom toiletries included. And if you need any assistance, our friendly team of experts is always on hand to help plan your perfect stay.

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