Vacation Rentals & Beach Rentals in Siesta Key

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147 beach rentals

Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 1 minutes

Match: Boat available Staffed property

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Price per night from

$267

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Tiny House Siesta - Sand Dollar – A private master loft and open living space

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$448

120 Steps to the Beach with beach gear included!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$424

Amazing views, 11th flr, On the beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$410

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Boat available, Staffed property

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Price per night from

$230

Banana Cabana: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$240

Palm Bay Club - 343: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$285

Amazing Beachfront Condo, Siesta Key,

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$345

FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN CONDO!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Staffed property

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Price per night from

$272

“Clean comfortable Siesta Key Condo with all the comforts of home...Perfect!” The condo is walking distance to shops, restaurants and quaint local tiki bar! The beach is a short walk across the street and through the beach-front section of the complex with lounge chairs and umbrellas available, very nice! I didn't mention the 2 pools (one beachside) and nice gym facilities also just downstairs of the unit. The covered parking space was an added plus! The condo was clean and very comfortable with all of the amenities of home which is greatly appreciated! You can even enjoy the view of the bayside inlet and beautiful landscaping from the kitchen through the entire wall of glass doors in the living/dining room! We had a wonderful week! The property owner Vic supplied more than enough information on the condo, local businesses and area maps! He was such a pleasure to work with! Thanks again Vic! We are already planning our next trip to Siesta Key in May!!

1 of 2 match: Boat available, Staffed property

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Price per night from

$144

Jamaica Royale #104! Completely renovated, Gulf side, beautiful 2b/2b Condo!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Staffed property

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Price per night from

$338

Gulf and Bay Club 3bdrm “E” Luxury END CORNER Unit - RIGHT ON BEACH

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Boat available, Staffed property

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Price per night from

$904

1 of 2 match: Boat available, Staffed property

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Price per night from

$285

1 of 2 match: Boat available, Staffed property

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Price per night from

$144

Private Beach Access - Home away from Home - 2 BR 2 BA - Furnished Condo

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$178

Ten35 Seaside - Island View: Residence 406

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$560

Ten35 Seaside - Island View: Residence 308

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$549

Living the Dream - Starfish: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$343

BEACH RESIDENCES on Siesta, aka The Hyatt – 3 Bed/3 Bath Luxury Penthouse

Siesta Key hotel apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$514

Ten35 Seaside - Island View: Residence 604

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$560

Ten35 Seaside - North Water View: Residence 606

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$778

Crescent Beach Villas - La Perlita: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$274

Ten35 Seaside - South Water View: Residence 502

Siesta Key condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$755

Crescent Beach Villas - La Estrella: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$274

Gulf Holiday: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$171

Ten35 Seaside - Direct Gulf View: Residence 501

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$949

Sun and Sea: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$285

Living the Dream - Pink Flamingo: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$320

Palm Bay Club - 303: By Beachside Management

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$343

Ten35 Seaside - North Water View: Residence 310

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$629

Ten35 Seaside - North Water View: Residence 506

Siesta Key condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$778

Ten35 Seaside - South Water View: Residence 302

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$606

Ten35 Seaside - Island View: Residence 408

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$549

Ten35 Seaside - Island View: Residence 404

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$549

Jamaica Royale - Beachfront Tower: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$377

Firethorn 610 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$142

Buttonwood 452 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$290

Firethorn 711 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Staffed property

1 of 2 filters match

Price per night from

$137

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