Rent Key West Homes with Swimming Pools

We selected the 452 homes worth renting in this location

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Key West

Rockpool

Rockpool

  • 8 guests

  • 4 bedrooms

Victoria Park, Fort Lauderdale

Located in the residential area of Victoria Park in Fort Lauderdale, this convenient spot offers the ideal set-up to those seeking a holiday by the beach not far from Miami. With plenty of workspaces and high-speed wi-fi here, it also suits those in town on workcations.

Who Is Love to You

Who Is Love to You

  • 6 guests

  • 3 bedrooms

Coral Ridge, Fort Lauderdale

This duplex apartment is spread over two floors and sits within a holiday complex on the waterways of Fort Lauderdale. Guests here have access to a shared swimming pool and barbecue area.

Cocktails on the Beach

Cocktails on the Beach

  • 8 guests

  • 4 bedrooms

Birch Park Finger Streets, Fort Lauderdale

Ideal for families, this lovely home can be found just a one-minute walk from Fort Lauderdale Beach. It’s split between the main house and a guest house, which offers a touch more privacy – it would be ideal for grandparents or a couple.

Tranquil Bay

Tranquil Bay

  • 12 guests

  • 4 bedrooms

Key Haven, Key West

This waterfront home is the perfect spot to bask in the sun, sea, and sand of the Florida Keys. The private boat dock is a highlight, allowing you to explore the vast beaches and reefs of Key West.


We selected the top 3% holiday homes in Key West Homes with Swimming Pools

Explore the 452 most perfect homes in our collection

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Most popular homes in Key West

Paradise Key

Paradise Key

  • 14 guests

  • 6 bedrooms

Key Haven, Key West

Lakeside Getaway

Lakeside Getaway

  • 18 guests

  • 9 bedrooms

Barrier Island, Fort Lauderdale

Floridian Retreat

Floridian Retreat

  • 16 guests

  • 6 bedrooms

Urban Estates, Vineyards

Sunshine With a View

Sunshine With a View

  • 11 guests

  • 4 bedrooms

Harbour Inlet, Fort Lauderdale

Citron Lime

Citron Lime

  • 4 guests

  • 2 bedrooms

South Middle River, Fort Lauderdale

The Tidal Flow

The Tidal Flow

  • 12 guests

  • 4 bedrooms

Key Haven, Key West

The Pearl of Key West

The Pearl of Key West

  • 16 guests

  • 6 bedrooms

Key Haven, Key West

Sunshine Magic

Sunshine Magic

  • 16 guests

  • 8 bedrooms

Coral Ridge, Fort Lauderdale

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Check upcoming rates & availability for Key West Homes with Swimming Pools


Frequently asked questions

Similar destinations

You've certainly come to the right place if you are hoping to find one of the finest Holiday Homes with Swimming Pools in Key West, Monroe County, Florida, United States. Our exclusive collection consists solely of homes that have passed our thorough 150-step vetting process with flying colours, so you can book with true peace of mind, knowing that everything from decibel levels in the bedroom to a room's intangible atmosphere has been tested and approved. We don't list a huge number of homes one our site, just the right ones. Each property in our collection comes fully furnished and ready to welcome you, with a fully-equipped kitchen, essential bathroom toiletries, and all linen included. Contact our dedicated team of experts to find the perfect luxury Key West Home to Rent with a Swimming Pool today, and set up a holiday to remember.

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