Vacation Rentals & Beach Rentals in Siesta Key

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139 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: Shared outdoor pool (heated) Pool or snooker table

All filters match

Price per night from

$267

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

Siesta Key apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated) Pool or snooker table

All filters match

Price per night from

$182

Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Shared outdoor pool (heated) Pool or snooker table

All filters match

Price per night from

$109

“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

Match: Shared outdoor pool (heated) Pool or snooker table

All filters match

Price per night from

$246

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: Shared outdoor pool (heated) Pool or snooker table

All filters match

Price per night from

$453

Bird of Paradise at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (heated) Pool or snooker table

All filters match

Price per night from

$490

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

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 56 minutes

Match: Shared outdoor pool (heated) Pool or snooker table

All filters match

Price per night from

$114

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“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: Pool or snooker table, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$435

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

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$339

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: Pool or snooker table, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$340

Siesta Key vaca rental

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Pool or snooker table, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$230

Frangi Pani at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pool or snooker table, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$490

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: Pool or snooker table, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$447

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: Pool or snooker table, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$228

Beach Vacation rental

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pool or snooker table, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$247

Ten35 Seaside - Direct Gulf View: Residence 601

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$927

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: Pool or snooker table, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$287

Siesta Key Villa

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$332

Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (heated), Pool or snooker table

1 of 2 filters match

Price per night from

$490

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (heated), Pool or snooker table

1 of 2 filters match

Price per night from

$490

Pineapple at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (heated), Pool or snooker table

1 of 2 filters match

Price per night from

$490

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: Pool or snooker table, 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: Pool or snooker table, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$131

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: Pool or snooker table, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$224

Family Tides - High Tides: By Beachside Management

Siesta Key apartment

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

1 of 2 match: Pool or snooker table, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$549

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, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$424

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Shared outdoor pool (heated), Pool or snooker table

1 of 2 filters match

Price per night from

$230

Orchid at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (heated), Pool or snooker table

1 of 2 filters match

Price per night from

$490

Coconut at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (heated), Pool or snooker table

1 of 2 filters match

Price per night from

$490

Split Leaf at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (heated), Pool or snooker table

1 of 2 filters match

Price per night from

$490

Amazing views, 11th flr, On the beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Pool or snooker table, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$410

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

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Pool or snooker table, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$332

Palm Bay Club - G46: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$285

Casa Mar - Unit 56: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pool or snooker table, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$263

Crescent Arms; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$411

Crescent Condos; by Beachside Management

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$514

Siesta Beach House; by Beachside Management

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$320

Sea Shell; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Pool or snooker table, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$320

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