Vacation Rentals & Beach Rentals in Siesta Key

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200 beach rentals

Vacation Waterfront Cottage

Myakka City cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Private outdoor pool (unheated) Swing set or jungle gym

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Price per night from

$157

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Siesta Key Beach | Private Pool

Fruitville house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$400

Beach house for rent in siesta key beach.

Siesta Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Responds fast! avg. 2 hours 0 minutes

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,002

University Park Country Club Property

Lakewood Ranch house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$481

BeautifulHome with Pool - 3 miles from Siesta Key Beach

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 38 minutes

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$241

Beautiful house for rent at siesta key beach with pool, theater and game room

Siesta Key house

  • 7 bedrooms
  • 3 bathrooms
  • sleeps 15

Responds fast! avg. 2 hours 0 minutes

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$2,850

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$274

Tropical Paradise

Bradenton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,002

Hibiscus Hideaway B - Top Floor Unit

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$283

Casa Sea Esta Executive Studio / Condo at Sara Cay

Tallevast studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$92

Spectacular views! By LoveRentals

Holmes Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$363

The Salty Dog on North Shore

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$389

New Coastal Pool + Game Room home - sleeps 10

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$567

Updated 4/2 pool home, 5 Mins to Siesta Key

Siesta Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 26 minutes

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$327

Zen Bungalow

Sarasota house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$258

Copacabana Boaters Dream Home in Anna Maria

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$416

Blue Heron Studio / Condo 2 miles from Airport!

Tallevast studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$119

GUEST HOUSE

Fruitville guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 29 minutes

1 of 2 match: Private outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$107

White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$630

+++ Clean & Bright +++ Minutes to Anna Maria Island

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

1 of 2 match: Private outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$178

Stunning & Serene +++ Minutes from Anna Maria Island, IMG Academy and more!

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

1 of 2 match: Private outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$114

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 outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$266

Responds fast! avg. 54 minutes

1 of 2 match: Private outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$267

River Strand Golf and Country Club Resort

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$229

Just Minutes from the White Sandy Siesta Beach

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“It was very cozy and comfortable apartment!” We loved to spend our vacation at this place. Really close to the beach, to different restaurants, and all kind of stores.

1 of 2 match: Private outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$115

LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$161

Florida Ocean Front Condo

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$622

Seaplace Condo - 1975 GMD 104

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$192

March 23-March 30, 2024 Springbreak 3bdr on the beach Longboat key

Longboat Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$745

Cozy & Bright+++Minutes to Anna Maria Island, IMG Academy and more

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

1 of 2 match: Private outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$117

Anna Maria Island/ IMG Academy/ Beach/ HotTub/ Bikes/ Kayaks/ Golf/ Fishing

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$287

Responds fast! avg. 11 minutes

1 of 2 match: Private outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$132

2 Bedroom, 2 Bathroom condo / Heated pool / 7 minute walk to beach

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$178

Beautiful home- Private getaway-Heated Pool/HotTub IMG 5 Close to Beaches

Palma Sola house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 22

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$831

Hibiscus Hideaway Condo Walk to Historic Bridge St

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$298

Sandy Oasis 4-bedroom with Pool Sarasota/Bradenton

Braden River house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 33 minutes

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$304

Luxury waterfront home with a heated pool and spa!

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$537

Quiet and Comfortable Condo Near Turtle Beach

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Siesta sweet spot” Great value for location. Nice pool, visits with the manitees. Close to everything. This time of year ocean water was amazing

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$201

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rentals in Siesta Key

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