Key West Homes for a Watersports Holiday

We selected the 296 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

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Home spotlights in Key West

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.

Keys to Paradise

Keys to Paradise

  • 14 guests

  • 6 bedrooms

Key Haven, Key West

If you’re seeking an authentic Florida Keys experience, then look no further. This home is located within a gated community, less than a mile from popular Key West.

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.

The Theodore

The Theodore

  • 16 guests

  • 6 bedrooms

Key Haven, Key West

This home offers an idyllic retreat in Key West. Outside, you can savour blissful days by the heated pool and there's a fire-pit for magical evenings under the stars.


We selected the top 3% holiday homes in Key West Homes for a Watersports Holiday

Explore the 296 most perfect homes in our collection

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Most popular homes in Key West

 Shellstone Magic

Shellstone Magic

  • 16 guests

  • 8 bedrooms

Key Haven, Key West

Moonlit Bay

Moonlit Bay

  • 10 guests

  • 4 bedrooms

Key Haven, Key West

Key Sunset

Key Sunset

  • 14 guests

  • 5 bedrooms

Key Haven, Key West

Salt and Serenity

Salt and Serenity

  • 10 guests

  • 4 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

The New Standard

The New Standard

  • 20 guests

  • 8 bedrooms

Key Haven, Key West

The Tidal Flow

The Tidal Flow

  • 12 guests

  • 4 bedrooms

Key Haven, Key West

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Find the best homes for a watersports holiday in Key West, Monroe County, Florida, United States. Every one of our properties has been meticulously vetted by our Plum Guide experts, so you don't have to worry about anything, from the WiFi speed to water pressure. All of our homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Arrange your getaway today, and stay in one of the best homes for a watersports holiday in Key West, Monroe County, Florida, United States.

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