Vacation Rentals & Beach Rentals in Siesta Key

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143 beach rentals

Stunning & Serene +++ Minutes from Anna Maria Island, IMG Academy and more!

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

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Price per night from

$113

Cozy & Bright+++Minutes to Anna Maria Island, IMG Academy and more

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

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Price per night from

$117

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Island Village Hideaway! Steps to Sand

Longboat Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$192

Beach Dreams -"Dream Away Villa"

Anna Maria Island cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$337

Crystal Sands Unit 308 Siesta Key, Florida

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Vacation Rental” We have been coming to Siesta Key for our Vacations for years... We have stayed at a number of Units at Crystal Sands, Crescent arms and El Presidente... Crystal Sands Unit 308 is one of the best Units we have stayed at... It has a great view of the Beach and Pool... You can watch the Sunsets and Moonsets right from the Lanai... The Unit is Roomy, Clean and had all the appliances, Dishes and Linens we needed... The Washer\Dryer in the Unit is very convenient... It has a New 60" Hdtv in the Living Room with an incredible picture... Jim left printed instructions for the Hdtv, Washer and Dryer which made it very easy to use the appliances in the Unit... We are looking forward to staying in Crystal Sands Unit 308 again for our next trip to Siesta Key...

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Price per night from

$428

BAY FRONT HOUSE WITH PRIVATE DOCK

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 31 minutes

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Price per night from

$343

SunWay Suites Unit 2 Plover

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$23

Island Hideaway! Bermuda-esque Guest House! Steps to the Sand!

Longboat Key guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$120

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$488

Downtown Apartment in Historic Burns Square downtown Sarasota

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$280

Beach Dreams "Tangerine Dreams Villa "

Bradenton Beach cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$343

Castnetter Beach Resort 2

Bradenton Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$314

Spacious Apt. #1 Historic Walkable Downtown, between Siesta & Lido Beach

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$481

Jamaica Royal Villas - Villa 42; by Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$239

Beach Dreams " Sweet Dreams Villa"

Anna Maria Island villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$516

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Price per night from

$331

St.Armands Circle condo ( Kingston Arms )

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 25 minutes

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Price per night from

$257

Cathy's Crescent Condos-Siesta Key, FL GULF FRONT

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great View” We stayed at Kathy’s condo during the 4th of July week. The Condo was great and the view was amazing. We enjoyed the fireworks display and easy access to the beach. We look forward to renting her condo again in the future.

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Price per night from

$313

Steps to beach and bay on beautiful Anna Maria Island

Bradenton Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$101

Charming Siesta Key Village Unbeatable Location

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$189

SunWay Suites Unit 4 Pelican

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$137

Beach house for rent in siesta key beach.

Siesta Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Responds fast! avg. 1 hour 59 minutes

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Price per night from

$999

Condo wOcean view on Siesta

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 33 minutes

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Price per night from

$400

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$229

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

“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!!

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Price per night from

$143

SunWay Suites Unit 1 Sandpiper

Sarasota apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$149

SunWay Suites Unit 3 Seagull

Sarasota apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$149

AUGUST SPECIAL! 2 min. drive to Siesta Key! Very Clean!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Wonderful Place to stay” Confortable, and quick easy drive to good restaurants and most important The Beach! Although it rained the whole weekend, we were close to our family for the birthday and bridal shower celebration.

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Price per night from

$211

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

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

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

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

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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