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Rent Siesta Key Homes with Swimming Pools

We selected the 10 homes worth renting in this location

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Home spotlights in Siesta Key

Gulfview Oasis

Gulfview Oasis

  • 14 guests

  • 6 bedrooms

Siesta Key, Sarasota County

This Siesta Key luxury rental property, known as 'Sunset Haven', offers breathtaking views of Siesta Key Beach and the Gulf of Mexico from multiple levels and a rooftop deck. With its exquisite design and incredible location on Siesta Key, just steps away from the beach and Siesta Key Village, this vacation rental is truly a coastal escape.

Siesta Key Serenity

Siesta Key Serenity

  • 14 guests

  • 6 bedrooms

Siesta Key, Sarasota County

Vunique Vacations presents Siesta Key Serenity, a luxury vacation home that offers a truly unforgettable experience for discerning travelers. With breathtaking views of Siesta Key Beach and the Gulf of Mexico, this nearly beachfront property boasts multiple levels and a rooftop deck.

Siesta Retreat

Siesta Retreat

  • 16 guests

  • 6 bedrooms

Siesta Key, Sarasota County

Vunique Vacations presents a distinct getaway for the discerning traveler seeking an unforgettable vacation experience. Located just across the street from Siesta Key Beach in Florida, this luxury townhome offers a truly captivating stay.

Siesta Key Retreat

Siesta Key Retreat

  • 14 guests

  • 6 bedrooms

Siesta Key, Sarasota County

This Nearly Beachfront, Siesta Key luxury rental property features views of Siesta Key Beach and the Gulf of Mexico from Multiple Levels and the Roof Top Deck. Offering a unique combination of comfort and elegance, this vacation rental provides a dream escape for guests seeking relaxation and tranquility.


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

Explore the 10 most perfect homes in our collection

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Most popular homes in Siesta Key

Live in Paradise

Live in Paradise

  • 12 guests

  • 5 bedrooms

Siesta Key, Sarasota County

Serene Seaside Villa

Serene Seaside Villa

  • 16 guests

  • 6 bedrooms

Siesta Key, Sarasota County

Gulf Breeze Retreat

Gulf Breeze Retreat

  • 18 guests

  • 7 bedrooms

Siesta Key, Sarasota County

Siesta Dream

Siesta Dream

  • 19 guests

  • 8 bedrooms

Siesta Key, Sarasota County

Luxury Coastal Escape

Luxury Coastal Escape

  • 16 guests

  • 6 bedrooms

Sarasota, Florida

Paradise Cove Retreat

Paradise Cove Retreat

  • 14 guests

  • 5 bedrooms

Sarasota County, Florida

Siesta Key Hideaway

Siesta Key Hideaway

  • 14 guests

  • 5 bedrooms

Sarasota County, Florida

Distinct Dunes

Distinct Dunes

  • 16 guests

  • 6 bedrooms

Sarasota, Florida

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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 Siesta Key, Sarasota 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 Siesta Key Home to Rent with a Swimming Pool today, and set up a holiday to remember.

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