Vacation Rentals & Beach Rentals in Siesta Key

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119 beach rentals

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Children's pool Shared outdoor pool (heated)

All filters match

Price per night from

$205

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

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 56 minutes

Match: Children's pool Shared outdoor pool (heated)

All filters match

Price per night from

$114

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Luxury Waterfront Views/Pool/1400sf/2 min to Beach

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$339

Siesta Key Gulf View Condo

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 33 minutes

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$447

Siesta Key vaca rental

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$229

Frangi Pani at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$489

4 minute flip flop walk to the beach! Starfish 2/2

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$337

Beach Vacation rental

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$246

Ten35 Seaside - Direct Gulf View: Residence 601

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$925

Best of both worlds! Fish in bay or go to beach!

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Modern place in an awesome location” My family really enjoyed our time at this place. It was very clean, a convenient end unit, and close to the beautiful beach. Having the Intracoastal and pool was great, too. Being fully stocked and 2 TVs was a welcome surprise. Thanks for a great stay!

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$228

Siesta Key/Derby Bay

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Perfect!” Our family really enjoyed staying here! The villa was very well maintained and cleaned. It was stocked with everything you would need. The owner was very responsive to any concerns. We had a super nice neighbor and my boys loved fishing off the dock. I would recommend renting a golf cart to go to the beach if you have children (with toys etc) or elderly people with walking concerns. It is quite a walk to get to the beach (because you also have to walk down to the cross walk then across the street). The beach in front of the Aloha Kai property is very wide (great because it was never crowded like in front of other resorts) but it was an even farther walk to the water. We have always stayed beach front but needed more rooms than were available in my booking time frame this year. This property has changed the way I will book on siesta in the future. My boys LOVED fishing everyday off the dock. They caught lots of cool fish right off the back. The street that this villa is on was very quiet for our stay. Everyone was very kind & the property is very beautiful! We hope to come back very soon! It was a wonderful experience.

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$287

“Great stay in Sarasota” My husband and our two daughters spent a wonderful four days in Sarasota. The townhome we stayed in was beautiful and had all the amenities we needed. We spent every day at the beach and relaxed at the townhome in the evenings. We would definitely stay here again and have recommended this place to our family and friends. Thanks Louie!

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$434

Siesta Key Villa

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$332

Family Tides - High Tides: By Beachside Management

Siesta Key apartment

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$548

120 Steps to the Beach with beach gear included!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$423

Beachfront Getaway in Siesta Key

Siesta Key townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Very comfortable, nice amenities and well run.” Loved the beach and the nearby restaurants. The free trolly ride was easy to use and a great way to go into the village.

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$224

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: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$390

Siesta Key beach & sunsets - 2018 Spring & Summer openings!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$131

Siesta Beach House; by Beachside Management

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$319

Crescent Arms; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$411

Palm Bay Club - G46: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$285

Sea Shell; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$319

Casa Mar - Unit 56: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$262

Crescent Condos; by Beachside Management

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$513

Amazing views, 11th flr, On the beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$409

Relaxing Condo on Siesta Key - Close to beach - Mermaids Rest

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$332

Siesta Key Beach Cottages on Crescent

Siesta Key cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (heated), Children's pool

1 of 2 filters match

Price per night from

$224

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: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$178

Bird of Paradise at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$489

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$320

Sol y Mar - Casita Sol: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$285

Crystal Sands - 206 Tower: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$262

Just Beachy: By Beachside Management

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$376

Ten35 Seaside - North Water View: Residence 606

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$776

A Somewhere Is Here - Changes in Attitude: By Beachside Management

Siesta Key apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$411

Siesta Dunes #300: By Beachside Management

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$331

Sol y Mar - Casita Mar: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$239

Ten35 Seaside - Island View: Residence 406

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$559

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