Vacation Rentals & Beach Rentals in Siesta Key

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220 beach rentals

Match: Private outdoor pool (heated) Safe

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Price per night from

$457

4 Bedroom with Gulf View Siesta Key FL Beach Fun

Siesta Key apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“Fantastic Location and Beautiful Accomodations” Our daughters and their families stayed here in February. The condo was everything we expected and more. It has a breathtaking view of the Gulf from the screened in lani which runs the width of the unit. The four bedrooms were perfect for our group of nine and the kitchen / dining area was well stocked with appliances , pots & pans , dishes , glassware , etc. Condo has easy access to heated pool and ample parking. Owner made the rental process smooth as silk , and we all felt right at home as soon as we had checked in. Right across street from world famous Siesta Beach. Would highly recommend.

Match: Private outdoor pool (heated) Safe

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Price per night from

$514

****Walk to Beach-5min! Waterfront Canal! Private Pool~spa~Kayaks, Bikes!

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private outdoor pool (heated) Safe

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Price per night from

$454

Buena Vida: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated) Safe

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Price per night from

$515

Dream beach, pool/spa retreat!

Siesta Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Private outdoor pool (heated) Safe

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Price per night from

$344

Siesta Key Waterfront Estate heated Pool Privacy!

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated) Safe

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Price per night from

$716

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Condo wOcean view on Siesta

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Safe, Private outdoor pool (heated)

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Price per night from

$401

Siesta Key - 2BR - Beachfront Condo on Crescent Beach - Heated Pool - Tennis Ct

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Safe, Private outdoor pool (heated)

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Price per night from

$303

BEACHFRONT CONDO - THREE BEDROOM - HEATED POOL - FREE BOAT DOCKS - RENOVATED

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Trip to paradise” Renting unit was very easy. Unit was the best layout was great. Amenities within we're well thought, out and for us anything we wanted was there including beach chairs. View of ocean was breath taking along with sunsets. I will come back again.

1 of 2 match: Safe, Private outdoor pool (heated)

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Price per night from

$311

Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Turtle Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Romantic place. Perfect for young families with small kids” Firshermans Cove is on a shore side. The views are amazing as well as beach which is clean and not crowded at all. Easy check in/out and very quiet place, was ideal in our case, young family with 1,5 old boy. It was nice stay and we hopefully come back again.

1 of 2 match: Safe, Private outdoor pool (heated)

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Price per night from

$266

Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Great location!” The unit was just as described and pictures matched. The view of the ocean and bay were gorgeous. The kitchen was well equipped and there were lots of toys and chairs for the beach.

1 of 2 match: Safe, Private outdoor pool (heated)

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Price per night from

$311

Turtle Beach - Gulf-Front Condo - 2BR - Free Boat Docks - Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Safe, Private outdoor pool (heated)

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Price per night from

$266

Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Upscale

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Excellent location for a great vacation!” This is the fifth time we have had the pleasure of vacationing at El Galeon. We love the location with the beautiful beach access and walking to restaurants. We love the Manasota Key and have been vacationing there for the last seventeen years. El Galeon Gulf Unit 2 is our favorite place to stay with plenty of space and everything we need for a wonderful stay. We have already reserved "our place" for 2015.

1 of 2 match: Safe, Private outdoor pool (heated)

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Price per night from

$266

Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Safe, Private outdoor pool (heated)

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Price per night from

$311

Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Renovated!

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Experience” This condo is well kept, clean and looks directly onto the Gulf of Mexico. We liked it because the furniture is up to date and replaced when it becomes worn. We also love the fact it is within walking distance of a good restaurant. In fact there is nothing about this rental that we don't like and that is why we return there year after year. A great choice for you to start a great experience!

1 of 2 match: Safe, Private outdoor pool (heated)

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Price per night from

$266

Siesta Key Beach Cottages on Crescent

Siesta Key cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Safe, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$224

Walk to Siesta Beach, Heated Pool w/BBQ, Parking

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 4 minutes

1 of 2 match: Safe, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$133

Zuva Sands

Siesta Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Safe, Private outdoor pool (heated)

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Price per night from

$252

White Sands Village - Unit 909

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Safe, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$115

Bayside Gulf and Bay Club

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Safe, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$172

Casa Covella

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Safe, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$219

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

1 of 2 match: Safe, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$999

Lovely Siesta Key house with heated pool - A block away from Siesta beach!

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Safe, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$492

Another Day in Paradise

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 1 minutes

1 of 2 match: Safe, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$544

Responds fast! avg. 4 minutes

1 of 2 match: Safe, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$228

Blue Lagoon; By Beachside Management

Siesta Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Safe, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$411

Chinaberry 415 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Safe, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$264

Firethorn 611 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Safe, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$142

Chinaberry 413 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Safe, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$264

Chinaberry 454 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Safe, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$264

Doveplum 621 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Safe, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$167

Chinaberry 943 at Midnight Cove Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Safe, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$171

Buttonwood 955 at Midnight Cove Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Safe, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$179

Doveplum 624 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Safe, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$167

Firethorn 522 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Safe, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$142

Firethorn 110 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Safe, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$249

Chinaberry 424 at Midnight Cove Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Safe, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$264

Firethorn 712 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Safe, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$142

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