Key West Homes for a Watersports Holiday

We selected the 298 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

0

Home spotlights in Key West

Key Lime Delight

Key Lime Delight

  • 16 guests

  • 5 bedrooms

Key Haven, Key West

Just minutes from the heart of Key West, this home is a laid-back waterfront escape with room for the whole crew. Five bedrooms, including a playful bunk room, make this home ideal for families and groups, while the open-plan layout keeps everyone connected.

The Tidal Flow

The Tidal Flow

  • 12 guests

  • 4 bedrooms

Key Haven, Key West

Set beside the water in a quiet gated community, this Key West retreat is all breezy days and golden-hour swims. Coastal tones and soft natural light bring a sense of calm throughout, while outside, the private pool, dock, and fenced garden make it easy to unwind.

The New Standard

The New Standard

  • 20 guests

  • 8 bedrooms

Key Haven, Key West

Waterfront, with its own private dock, landscaped lawns, pool, jacuzzi, ping pong table, and outdoor kitchen, it is all about outdoor living in this sprawling three-storey home. Inside you'll find bright and beachy whitewash interiors, pops of sea blue and natural wood that only accentuate the laid-back lifestyle that comes with the territory.

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 298 most perfect homes in our collection

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Most popular homes in Key West

Waterfront Pearl

Waterfront Pearl

  • 16 guests

  • 8 bedrooms

Key Haven, Key West

The Pearl of Key West

The Pearl of Key West

  • 16 guests

  • 6 bedrooms

Key Haven, Key West

Key West Retreat

Key West Retreat

  • 12 guests

  • 4 bedrooms

Key Haven, Key West

Tranquil Bay

Tranquil Bay

  • 12 guests

  • 4 bedrooms

Key Haven, Key West

Keys to Paradise

Keys to Paradise

  • 14 guests

  • 6 bedrooms

Key Haven, Key West

Paradise Key

Paradise Key

  • 14 guests

  • 6 bedrooms

Key Haven, Key West

Salt and Serenity

Salt and Serenity

  • 10 guests

  • 4 bedrooms

Key Haven, Key West

 Shellstone Magic

Shellstone Magic

  • 16 guests

  • 8 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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