Seaside Rentals in Key West

Curated Seaside Rentals and cottages in Key West

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Adults

Age 13+

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Age 1 to 12

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Home spotlights in Key West

Salt and Serenity

Salt and Serenity

  • 10 guests

  • 4 bedrooms

Key Haven, Key West

Tucked along the water’s edge just minutes from Key West, this breezy four-bedroom retreat blends comfort with coastal charm. With a private heated pool, gated garden, and dock for boats up to 50 feet, it’s made for both downtime and days on the water.

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.

Dream of the Open Sea

Dream of the Open Sea

  • 12 guests

  • 6 bedrooms

Harbour Inlet, Fort Lauderdale

Floor-to-ceiling windows mean that you don’t even have to try to tear your eyes away from the water view here. This home sits on the edge of Harbor Inlet, looking out over the Port Everglades waterway.

Lakeside Getaway

Lakeside Getaway

  • 18 guests

  • 9 bedrooms

Barrier Island, Fort Lauderdale

This dream Fort Lauderdale retreat is perfect for families and large groups. Set right on the Mayan Lake, it offers three private suites – each with their own living space, kitchen, and dining area.


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

Explore the 412 most perfect homes in our collection

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Most popular homes in Key West

Island Sophisticate

Island Sophisticate

  • 16 guests

  • 6 bedrooms

Key Haven, Key West

Summer Lights

Summer Lights

  • 6 guests

  • 3 bedrooms

Harbour Inlet, Fort Lauderdale

Naples Aglow

Naples Aglow

  • 8 guests

  • 4 bedrooms

Old Naples, Naples

Tranquil Bay

Tranquil Bay

  • 12 guests

  • 4 bedrooms

Key Haven, Key West

True Pearl

True Pearl

  • 8 guests

  • 4 bedrooms

Bermuda Riviera, Fort Lauderdale

Sunshine Magic

Sunshine Magic

  • 16 guests

  • 8 bedrooms

Coral Ridge, Fort Lauderdale

Key Sunset

Key Sunset

  • 14 guests

  • 5 bedrooms

Key Haven, Key West

 Marina Living

Marina Living

  • 18 guests

  • 8 bedrooms

Key Haven, Key West

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Frequently asked questions

Similar destinations

Explore our collection of Seaside Rentals in Key West, Monroe County, Florida, United States. Every property in our curated selection is fully furnished and meticulously equipped, offering the finest amenities for a seamless stay. From well-appointed kitchens to luxurious linens, we ensure every detail is covered. Picture yourself unwinding in the serene coastal atmosphere of one of our luxury homes. Our dedicated team of experts is here to help you find the ideal seaside retreat for your next getaway. Book today and experience the ultimate in coastal living.

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