Vacation Rentals & Beach Rentals in Siesta Key

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153 beach rentals

Monthly Rental, 2 bed, 2 bath, Ocean view.

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated) Shared indoor pool

All filters match

Price per night from

$115

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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: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$228

2 bedroom Condo Bay Oaks Siesta Key

Sarasota condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$573

“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: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$434

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

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$338

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: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$447

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: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$339

Siesta Key vaca rental

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$229

Relaxing and quite apartment in a great location

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$189

The Meadows golf course view villa

North Sarasota villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$122

Beach Vacation rental

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, 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: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$927

Frangi Pani at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$489

Beachplace Building 7 Great View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$180

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: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$287

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$122

"Lido Lookout" Beach Paradise Private Home on Lido Key

Lido Key house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$2,977

Piece of Paradise

Sarasota townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$109

Private Retreat on Siesta Dr

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 49 minutes

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$516

St Armand's Private Home on Jackson Drive

Lido Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$382

Just another day in paradise! Sunrise condominiums!

Bee Ridge condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$115

Siesta Key Villa

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$332

3BR 2BTH 1180sqft Condo 15 Minutes From Beaches

Sarasota apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$75

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$131

Great location, quiet, peaceful, and comfortable

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$46

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: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$224

120 Steps to the Beach with beach gear included!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$424

Live like a Millionaire

Fruitville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$229

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: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$390

Family Tides - High Tides: By Beachside Management

Siesta Key apartment

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$549

Amazing views, 11th flr, On the beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$409

Sarasota 2BR 2BTH Condo Close to Siesta Key Beach

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$60

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

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$332

~ SUPER SPECIAL from $99/night ~ OCEAN FRONT DLX STUDIO

Longboat Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 1 hour 56 minutes

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$194

Casa Mar - Unit 56: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$263

Palm Bay Club - G46: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$286

Siesta Beach House; by Beachside Management

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$320

Crescent Arms; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$411

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rentals in Siesta Key

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