Vacation Rentals & Beach Rentals in Siesta Key

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143 beach rentals

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

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$267

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

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$457

Once Upon a Tide: By Beachside Management

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$400

Buena Vida: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$514

A Tide That Binds Us - 602: By Beachside Management

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$491

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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Price per night from

$178

Beach Walk: By Beachside Management

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$514

Casa Mar - Unit 56: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$262

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

Siesta Key apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$457

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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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

Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$489

Orchid at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$490

Coconut at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$490

Split Leaf at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$489

Siesta Beach House; by Beachside Management

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$320

Costal Surfside Swank 302: By Beachside Management

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$514

Banana Cabana: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$240

Direct Beachfront Delight: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$240

Hidden Paradise - Bungalow 2; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$285

Palm Bay Club - 343: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$285

Crescent Arms; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$411

Beach House Residence - Penthouse; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$434

Costal Surfside 298: By Beachside Management

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$457

Palm Bay Club - G46: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$285

Hidden Paradise - Bungalow 1; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$285

Crescent Condos; by Beachside Management

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$514

Costal Surfside 304: By Beachside Management

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$297

Super Cute Cottage--Private--Walk/Bike to Beach

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$258

Three bedroom house directly on beach with gulf vi

Siesta Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

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Price per night from

$402

Bird of Paradise at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$490

2BR/2BA House Just Steps to Siesta Village & Siesta Key Beach

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Location, Very Well Appointed” This house is perfectly located right in Siesta Key Village within an easy walk to shops and restaurants. It is also just a block from the beach. No parking hassles! The house is very well appointed. The owner has thoughtfully provided more than enough coffee for the Keurig, lots of towels, and all needed kitchen utensils, dishes, containers, and cooking supplies, in addition to a beach wagon and chairs. Although not luxurious, this is a very comfortable rental. We also liked the privacy of having our own house. The only negatives were the lack of towel racks in the bathrooms and the lack of hot water in the bathroom with the tub (it remained only warm, even after running for a very long time). The water in the other bathroom was fine.

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Price per night from

$316

Ocean Vue - Unit A: By Beachside Management

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$514

Ten35 Seaside - Island View: Residence 406

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$560

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