Vacation Rentals & Beach Rentals in Siesta Key

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51 beach rentals

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Beautiful Crescent Beach on Siesta Key One of the

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$301

Amazing Beachfront Condo, Siesta Key,

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$345

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$272

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

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$431

Beachfront Condo Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great place” We couldn't have a better time. The condo had everything you could possibly need for cooking, or going to the pool and beach. The condo is a 3 minute walk to the beach, and the weather was perfect. Village is a 5 minute drive and the restaurants were perfect for a family. Definitely coming back!

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$454

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.

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$516

Three bedroom house directly on beach with gulf vi

Siesta Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$402

“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!!

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$144

Sea Shell Condo-Right On Crescent Beach-Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 23 minutes

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$391

Siesta Key - 2bdrm on the beach - amazing views!!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Escape from reality” We had an amazing vacation. Accommodations were great and very comfortable. Breakfast on the lanai and sunset fishing on the beach were 2 of our families favorite things to do. You also have the bay right behind you where you can kayak or paddle board. The community was quiet which was prefect for our getaway. We will definitely be staying here again.

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$603

Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$109

Another Day in Paradise

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 1 minutes

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$546

Gulf and Bay Club 3bdrm “E” Luxury END CORNER Unit - RIGHT ON BEACH

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$905

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$230

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$285

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

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$278

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

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$267

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$144

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.

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$660

Fanta-Sea 53: By Beachside Management

Siesta Key townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$630

Ten35 Seaside - South Water View: Residence 302

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$607

Living the Dream - Mermaid: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$344

Our House at the Beach - 502: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$321

Las Palmas; by Beachside Management

Siesta Key house

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$1,204

Fanta-Sea 49: By Beachside Management

Siesta Key house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$860

Ten35 Seaside - North Water View: Residence 310

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$630

Lookout: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 10

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$745

Ten35 Seaside - North Water View: Residence 506

Siesta Key condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$780

Ten35 Seaside - North Water View: Residence 606

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$780

Fanta-Sea 47; By Beachside Management

Siesta Key townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$458

Crystal Sands - 803 Tower; By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$298

Ten35 Seaside - South Water View: Residence 502

Siesta Key condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$757

Ten35 Seaside - Direct Gulf View: Residence 501

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$952

Magnificent Bayfront Condo - Resort Living on the Bay

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$161

Excellent Location - Gulf/Beach View - Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 38 minutes

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$345

Ten35 Seaside - Direct Gulf View: Residence 405

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$858

Ten35 Seaside - Direct Gulf View: Residence 301

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$858

Ten35 Seaside - Direct Gulf View: Residence 403

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$858

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