Houses Longboat Key

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459 houses

Match: Rental types Private outdoor pool (unheated) Safe

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Price per night from

$343

#1 EXCLUSIVE Siesta Key Beach House /3 payments

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Rental types Private outdoor pool (unheated) Safe

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Price per night from

$258

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Rental types Private outdoor pool (unheated) Safe

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Price per night from

$149

These homes match some but not all of your filters. Clear all filters

Beach house for rent in siesta key beach.

Siesta Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Responds fast! avg. 2 hours 4 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$1,001

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 4 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$2,831

Tropical Paradise

Bradenton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$1,001

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

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$241

Zen Bungalow

Sarasota house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$258

New Coastal Pool + Game Room home - sleeps 10

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$566

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

Siesta Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 43 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$326

Spectacular views! By LoveRentals

Holmes Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 22 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

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Price per night from

$363

Hibiscus Hideaway B - Top Floor Unit

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 22 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

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Price per night from

$315

The Salty Dog on North Shore

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 22 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

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Price per night from

$389

Copacabana Boaters Dream Home in Anna Maria

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 22 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$416

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

Palma Sola house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 22

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$829

Hibiscus Hideaway Condo Walk to Historic Bridge St

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 22 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$298

Luxury waterfront home with a heated pool and spa!

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 22 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$537

Responds fast! avg. 3 hours 41 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$192

Responds fast! avg. 3 hours 41 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$201

Responds fast! avg. 3 hours 41 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$132

Responds fast! avg. 3 hours 41 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$203

Responds fast! avg. 3 hours 41 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$165

Minutes to Anna Maria Island Beaches, Bring the Boat/Jet Ski, Private Pool

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 41 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$185

Responds fast! avg. 3 hours 41 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$168

Responds fast! avg. 3 hours 41 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$192

Responds fast! avg. 3 hours 41 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$236

Responds fast! avg. 3 hours 41 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$201

Responds fast! avg. 3 hours 41 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$185

Responds fast! avg. 3 hours 41 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$133

Responds fast! avg. 3 hours 41 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$218

Private Saltwater Pool, 5 minutes to Bradenton Beach, Superb location near Walki

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 3 hours 41 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$168

Responds fast! avg. 3 hours 41 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$161

Private Pool Oasis Home - Near Beaches- Great Neighborhood

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 41 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$196

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$309

Responds fast! avg. 4 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$231

Florida Paradise Near Img Academy and Beach

Oneco house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$406

Lookout: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 40 minutes

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$743

Firethorn 830 at Midnight Cove Siesta Key

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Safe, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$142

Viewing 38 of 459
rentals in Longboat Key

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