Vacation Rentals & Beach Rentals in Siesta Key

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254 beach rentals

Another Day in Paradise

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 1 minutes

Match: Private outdoor pool (heated) Sea view

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Price per night from

$545

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) Sea view

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Price per night from

$514

Las Palmas; by Beachside Management

Siesta Key house

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

Match: Private outdoor pool (heated) Sea view

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Price per night from

$1,202

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Condo wOcean view on Siesta

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 33 minutes

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

1 of 2 filters match

Price per night from

$402

Siesta Key Beach Cottages on Crescent

Siesta Key cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$224

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: Sea view, Private outdoor pool (heated)

1 of 2 filters match

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: Sea view, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$266

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

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

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: Sea view, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$311

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: Sea view, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$303

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: Sea view, Private outdoor pool (heated)

1 of 2 filters match

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: Sea view, Private outdoor pool (heated)

1 of 2 filters match

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: Sea view, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$266

Siesta Key Waterfront Estate heated Pool Privacy!

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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

1 of 2 filters match

Price per night from

$716

Zuva Sands

Siesta Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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

1 of 2 filters match

Price per night from

$252

White Sands Village - Unit 909

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$164

Casa Covella

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$219

Bayside Gulf and Bay Club

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$219

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: Sea view, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$133

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

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

1 of 2 filters match

Price per night from

$1,001

Dream beach, pool/spa retreat!

Siesta Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

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

1 of 2 filters match

Price per night from

$345

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

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$455

Responds fast! avg. 4 minutes

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

1 of 2 filters match

Price per night from

$228

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: Sea view, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$492

Buena Vida: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

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

1 of 2 filters match

Price per night from

$515

Blue Lagoon; By Beachside Management

Siesta Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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

1 of 2 filters match

Price per night from

$411

Firethorn 610 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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

1 of 2 filters match

Price per night from

$142

Chinaberry 424 at Midnight Cove Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$264

Buttonwood 950 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$205

Firethorn 711 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$137

Firethorn 514 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$137

Firethorn 332 at Midnight Cove Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$249

Doveplum 112 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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

1 of 2 filters match

Price per night from

$629

Chinaberry 456 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$264

Firethorn 513 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$142

Chinaberry 454 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$264

Doveplum 524 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$167

Firethorn 320 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$249

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