Vacation Rentals & Beach Rentals in Siesta Key

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398 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

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$266

Crescent Beach Villas - La Estrella: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$274

Siesta Key Townhouse across from Pristine Sands of Siesta Key 2B/2B sleeps 6

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Fantastic week in Siesta Key” The townhouse was fantastic and fully equipped with everything we needed for a very comfortable week. The location was outstanding - right across from the beach and the free trolley to the Village stopped right outside. The garage had everything the family needed to take to the beach and we met some lovely people around the pool. Thank you Michelle for your hospitality - we hope to be back soon.

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$190

Just Minutes from the White Sandy Siesta Beach

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“It was very cozy and comfortable apartment!” We loved to spend our vacation at this place. Really close to the beach, to different restaurants, and all kind of stores.

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$115

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$337

Amazing views, 11th flr, On the beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$410

Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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$109

“Anniversary Trip” Had a wonderful time at LA Siesta Condominiums for our anniversary vacation. Beautifully furnished and do close to the best beach in the USA

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$246

Siesta Key beach & sunsets - 2018 Spring & Summer openings!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$131

GULF FRONT ON #1 Beach! Siesta Dunes (by owner)

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Perfect, Perfect, Perfect” Nice condo with everything close by! Owners were great to deal with and as stated it would be . We plan on visiting again and would recommend this place to anyone.

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$272

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$458

BEAUTY ON THE BEACH! Crescent Arms 601S FULL FRONT VIEW

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$315

#1 EXCLUSIVE Siesta Key Beach House /3 payments

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$258

Renovated Beach Front 2BR/2BA Condo, Steps to beach, Gulf of Mexico Views

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$278

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.

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$515

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$272

Once Upon a Tide: By Beachside Management

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$401

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$178

A Somewhere is Here - Changes in Latitude: By Beachside Management

Siesta Key apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

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$458

Dream beach, pool/spa retreat!

Siesta Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

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$344

Family Tides - High Tides: By Beachside Management

Siesta Key apartment

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

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$550

Siesta Key Waterfront Estate heated Pool Privacy!

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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$717

Two bedroom, two bath condo by Siesta Key Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$459

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$320

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

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$454

Buena Vida: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$515

A Tide that Binds Us - 600: By Beachside Management

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

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$378

A Tide That Binds Us - 602: By Beachside Management

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

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$492

Beach Walk: By Beachside Management

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$515

Casa Mar - Unit 56: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$263

A Somewhere Is Here - Changes in Attitude: By Beachside Management

Siesta Key apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$412

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Sand Castle Suites - The Starfish

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$206

Tiny House Siesta - Yellow Lifeguard Stand Tiny House

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$422

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

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$448

Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$490

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$490

Pineapple at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$490

Sea Shell Condo-Right On Crescent Beach-Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 23 minutes

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Price per night from

$390

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rentals in Siesta Key

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