Vacation Rentals & Beach Rentals in Siesta Key

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391 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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$265

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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$189

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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$114

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$336

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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$245

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$457

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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$276

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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$512

Two bedroom, two bath condo by Siesta Key Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$457

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$319

Once Upon a Tide: By Beachside Management

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$400

Buena Vida: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

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$513

A Tide that Binds Us - 600: By Beachside Management

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

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$377

Sand Castle Suites - The Starfish

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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$205

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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$513

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

Siesta Key apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

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$457

Dream beach, pool/spa retreat!

Siesta Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

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$343

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

Siesta Key apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

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$411

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$130

Family Tides - High Tides: By Beachside Management

Siesta Key apartment

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

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$547

Amazing views, 11th flr, On the beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$408

#1 EXCLUSIVE Siesta Key Beach House /3 payments

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$257

Siesta Key Waterfront Estate heated Pool Privacy!

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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$713

Casa Mar - Unit 56: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$262

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$270

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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$270

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

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$452

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$313

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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$177

Beautiful, Affordable Close to famous Siesta Beach

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“It was wonderful!” Everything about the trip and condo was great! Mike met us to give us the keys and we called him for suggestions about restaurants, etc. and he was very helpful. The condo was very clean and had everything we needed. It was also great that we were able to use the beach chairs and umbrella. I am already trying to figure out when we can go again.

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$162

Pineapple at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$488

Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$488

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$488

Luxury Village Townhouse w/ Gulf and Beach Views

Siesta Key townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

“A wonderful home in an equally wonderful location.” The home provides a truly enjoyable family situation. The quality of the furnishings is very nice, the living space is very well maintained and clean and my interaction with the owner was always timely and courteous. My wife and I shared the home with our 14 year old granddaughter during our stay and the quiet enjoyment of the pool and the easy 1-2 minute walk to the Gulf of Mexico and the 5 minute walk to the heart of Siesta Key Village made the location hard to beat. Except for our day trips no car was needed. This is our second stay in the home and we will look to reserving it for our next visit. There were absolutely no disappointments only wonderful experiences.

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$656

Beach Road - Bari

Siesta Key studio

  • Studio
  • 1 bathroom
  • sleeps 3

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$79

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