Vacation Rentals & Beach Rentals in Siesta Key

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148 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

Match: Pool or snooker table Staffed property

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Price per night from

$267

Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Pool or snooker table Staffed property

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Price per night from

$109

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

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Pool or snooker table Staffed property

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Price per night from

$904

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.

Match: Pool or snooker table Staffed property

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Price per night from

$516

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!

Match: Pool or snooker table Staffed property

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Price per night from

$453

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Pool or snooker table Staffed property

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Price per night from

$230

*** SUPER SPECIAL RATES at Harbor Towers ***

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 56 minutes

Match: Pool or snooker table Staffed property

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Price per night from

$114

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Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Staffed property, Pool or snooker table

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Price per night from

$490

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Staffed property, Pool or snooker table

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Price per night from

$490

Pineapple at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Staffed property, Pool or snooker table

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Price per night from

$490

Orchid at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Staffed property, Pool or snooker table

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Price per night from

$490

Coconut at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Staffed property, Pool or snooker table

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Price per night from

$490

Split Leaf at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Staffed property, Pool or snooker table

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Price per night from

$490

Bird of Paradise at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Staffed property, Pool or snooker table

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Price per night from

$490

Siesta Key Beach : 2 Bedroom, 3 Beds, 3 Bathroom Duplex & Heated Pool

Siesta Key apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Staffed property, Pool or snooker table

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Price per night from

$182

Tiny House Siesta - Sand Dollar – A private master loft and open living space

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Pool or snooker table, Staffed property

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Price per night from

$448

120 Steps to the Beach with beach gear included!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Staffed property

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Price per night from

$424

Amazing views, 11th flr, On the beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Pool or snooker table, Staffed property

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Price per night from

$410

Banana Cabana: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Staffed property

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Price per night from

$240

Palm Bay Club - 343: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Staffed property

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Price per night from

$286

“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

1 of 2 match: Staffed property, Pool or snooker table

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Price per night from

$246

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Staffed property

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Price per night from

$272

1 of 2 match: Pool or snooker table, Staffed property

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Price per night from

$285

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Staffed property

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Price per night from

$338

Private Beach Access - Home away from Home - 2 BR 2 BA - Furnished Condo

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Staffed property

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Price per night from

$178

1 of 2 match: Pool or snooker table, Staffed property

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Price per night from

$144

“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: Pool or snooker table, Staffed property

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Price per night from

$144

BEACH RESIDENCES on Siesta, aka The Hyatt – 3 Bed/3 Bath Luxury Penthouse

Siesta Key hotel apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Staffed property

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Price per night from

$516

Living the Dream - Pink Flamingo: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Pool or snooker table, Staffed property

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Price per night from

$320

Living the Dream - Starfish: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Pool or snooker table, Staffed property

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Price per night from

$343

Ten35 Seaside - North Water View: Residence 506

Siesta Key condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Pool or snooker table, Staffed property

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Price per night from

$779

Jamaica Royale - Beachfront Tower: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Staffed property

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Price per night from

$378

Ten35 Seaside - South Water View: Residence 502

Siesta Key condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Pool or snooker table, Staffed property

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Price per night from

$756

Ten35 Seaside - Island View: Residence 408

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 of 2 match: Pool or snooker table, Staffed property

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Price per night from

$550

Ten35 Seaside - Island View: Residence 406

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Staffed property

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Price per night from

$561

Ten35 Seaside - Island View: Residence 308

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Staffed property

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Price per night from

$550

Ten35 Seaside - Island View: Residence 404

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 of 2 match: Pool or snooker table, Staffed property

1 of 2 filters match

Price per night from

$550

Ten35 Seaside - South Water View: Residence 602

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Staffed property

1 of 2 filters match

Price per night from

$688

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