Vacation Rentals & Beach Rentals in Siesta Key

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106 beach rentals

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3BR/4BA TOWNHOUSE - POOL VIEW PARADISE - PRIVATE BEACH ACCESS

Siesta Key townhouse

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 38 minutes

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Price per night from

$428

Sandy Toes Town Home

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Time in Paradise” We recently had the luck to spend two months in paradise. This condo was comfortably appointed, well stock to meet all our needs, and most importantly in the perfect location. The beach was a short walk to the left and stores and restaurants were just a short walk to the right. We had a great time and enjoyed everything Sarasota, Siesta Key, and this Sandy Toes Condo had to offer. Thanks Mark!

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Price per night from

$271

A Siesta Tropical Retreat - Island Pool Oasis in Village & 2 blocks to Beach

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

“Your best choice for location!” We stayed for 10 lovely days in this home and I have to say It was an even better location than I expected. Everything you could want to do is in walking distance or you can walk to the village (maybe a 3 minute walk)and hop in a free taxi . The house is well appointed and beds are very comfortable. We traveled with a 10 yr.old, 11yr. old , and 15 yr. old my 15 yr. old niece slept in the trundle bed and commented on how comfortable the bed was. In the kitchen you will find a drawer full of menus for the many nearby restaurants and information for water activities. I highly recommend parasailing while your there ! Considering how close everything is the street is very quiet and the owners were great to deal with. Thanks Kathi and Grant!

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Price per night from

$499

Siesta Key private beach access

Siesta Key villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Siesta Key Townhouse” This was a wonderful place to stay! The house was very clean and spacious and had everything we needed for a week at the beach.

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Price per night from

$507

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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Price per night from

$189

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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Price per night from

$265

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

$400

Lakefront Oasis 3 Bdrm House with Heated Pool minutes from village and beach

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$685

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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Price per night from

$114

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

$314

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

$177

Pineapple at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$488

Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$488

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$488

Orchid at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$488

Bird of Paradise at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$488

Coconut at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$488

Split Leaf at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$488

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Price per night from

$456

Siesta Key- Beach Chic Retreat, Siesta Key 3 Bedroom 2 Bath Apartment

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

“This was the definition of home away from home” great value for your money...very cozy, with lots of new upgrades. Easy access to the beach and restaurants.

Responds fast! avg. 1 hour 14 minutes

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Price per night from

$314

Siesta Key 2 Bedroom 1 Bath Modern/Contemporary Decor Apartment

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Amazing!” I stayed here with my husband and we had a great time! We were in Orlando visiting family and we decided to arrange some us time. The condo was excellent and very clean! Kathy and her husband were very informative, respond quickly,and available when we needed them. What was great was that we had all beach items available to us and were very useful. We were in close proximity to everything and the beach and restaurants were great! Everyone in the area was very friendly and my husband and I want to definitely come back!

Responds fast! avg. 1 hour 14 minutes

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Price per night from

$223

Siesta key Guest House 5 star on the water Private

Siesta Key guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$229

Palm Bay Club - 343: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$284

Ten35 Seaside - Direct Gulf View: Residence 301

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$855

Costal Surfside 298: By Beachside Management

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$456

Our House at the Beach, Lake House - C103; By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$319

Once Upon a Tide: By Beachside Management

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$399

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

$490

Our House at the Beach - 501: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$341

Jamaica Royale - Beachfront Tower: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$376

Crescent Arms; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$410

Casa Mar - Unit 22: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$262

Siesta Dunes #300: By Beachside Management

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$330

Ocean Vue - Unit A: By Beachside Management

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$513

Just Beachy: By Beachside Management

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$376

Living the Dream - Pink Flamingo: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$319

Ten35 Seaside - North Water View: Residence 506

Siesta Key condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$775

Ocean Vue - Unit B: By Beachside Management

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$524

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