Vacation Rentals & Beach Rentals in Siesta Key

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28 beach rentals

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Vacation Waterfront Cottage

Myakka City cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Swing set or jungle gym Smoking allowed

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Price per night from

$157

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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: Smoking allowed, Swing set or jungle gym

1 of 2 filters match

Price per night from

$114

GUEST HOUSE

Fruitville guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 29 minutes

1 of 2 match: Smoking allowed, 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: Smoking allowed, 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: Smoking allowed, Swing set or jungle gym

1 of 2 filters match

Price per night from

$178

6122

Englewood house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Smoking allowed

1 of 2 filters match

Price per night from

$114

5 min to the Beach, Sleeps 6

Nokomis house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Smoking allowed

1 of 2 filters match

Price per night from

$137

The Hideaway: 4/2 W Heated Pool and Outdoor Spaces, 10 mins to Sarasota Beach

Gulf Gate Estates house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Swing set or jungle gym, Smoking allowed

1 of 2 filters match

Price per night from

$373

Blue Heron Inn: 1/1 Spacious Apartment, 15 mins to beaches, pet friendly

Oneco apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Swing set or jungle gym, Smoking allowed

1 of 2 filters match

Price per night from

$126

1 of 2 match: Swing set or jungle gym, Smoking allowed

1 of 2 filters match

Price per night from

$172

Lady Palm Apt: 1/1 with 2 beds, garden vibes and outdoor spaces! Pet friendly

Bradenton apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Swing set or jungle gym, Smoking allowed

1 of 2 filters match

Price per night from

$144

Delightful Oasis #2

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Smoking allowed

1 of 2 filters match

Price per night from

$178

1 of 2 match: Swing set or jungle gym, Smoking allowed

1 of 2 filters match

Price per night from

$315

River Strand Golf and Country Club Resort

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Smoking allowed, Swing set or jungle gym

1 of 2 filters match

Price per night from

$229

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: Smoking allowed, Swing set or jungle gym

1 of 2 filters match

Price per night from

$266

Responds fast! avg. 54 minutes

1 of 2 match: Smoking allowed, Swing set or jungle gym

1 of 2 filters match

Price per night from

$267

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: Smoking allowed, Swing set or jungle gym

1 of 2 filters match

Price per night from

$117

Florida Ocean Front Condo

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Smoking allowed, Swing set or jungle gym

1 of 2 filters match

Price per night from

$622

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: Smoking allowed, 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: Smoking allowed, Swing set or jungle gym

1 of 2 filters match

Price per night from

$161

Seaplace Condo - 1975 GMD 104

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Smoking allowed, 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: Smoking allowed, Swing set or jungle gym

1 of 2 filters match

Price per night from

$745

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: Smoking allowed, Swing set or jungle gym

1 of 2 filters match

Price per night from

$178

Responds fast! avg. 12 minutes

1 of 2 match: Smoking allowed, Swing set or jungle gym

1 of 2 filters match

Price per night from

$144

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

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Smoking allowed, Swing set or jungle gym

1 of 2 filters match

Price per night from

$287

House of Blues - Lovely 2-Bedroom Condo with Pool, W&D and Patio

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Smoking allowed

1 of 2 filters match

Price per night from

$201

1 of 2 match: Swing set or jungle gym, Smoking allowed

1 of 2 filters match

Price per night from

$274

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

1 of 2 match: Swing set or jungle gym, Smoking allowed

1 of 2 filters match

Price per night from

$149

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