Houses Longboat Key

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Chinaberry 924 at Midnight Cove Siesta Key, FL.

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$171

NW Bradenton Exectitive Home

Bradenton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Rental types Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$492

Firethorn 830 at Midnight Cove Siesta Key

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Rental types Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$142

Responds fast! avg. 4 minutes

Match: Rental types Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$264

Lower Pricing! Stunning Heated Pool, Lanai w/ TV

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 4 minutes

Match: Rental types Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$184

Midcentury modern pool home on Siesta Key w/ gorgeous backyard

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 4 minutes

Match: Rental types Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$303

Steps to Siesta Key Beach, Pool/Spa/Tiki Bar

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 4 minutes

Match: Rental types Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$316

Responds fast! avg. 4 minutes

Match: Rental types Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$228

Large Pool Home, BBQ, YouTube TV, One Level

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 4 minutes

Match: Rental types Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$136

Doveplum 221 at Midnight Cove Siesta Key, FL.

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$256

Private Pool, 6 Mins Beach, 2 Family Rooms, Cable

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 4 minutes

Match: Rental types Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$162

Great Private Pool, Heat Extra, 2.5 miles to Beach, Dog Allowed, WiFi/Cable, BB

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 4 minutes

Match: Rental types Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$131

Hibiscus Hideaway Condo Walk to Historic Bridge St

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 40 minutes

Match: Rental types Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$298

Responds fast! avg. 4 minutes

Match: Rental types Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$329

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

Palma Sola house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 22

Match: Rental types Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$831

Priced Right Near Arlington Park Outdoor Kitchen

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 4 minutes

Match: Rental types Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$186

Lower Prices! Private Pool, WiFi, King Master w/En-suite, Garage, Washer/Dryer,

Gulf Gate Estates house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 4 minutes

Match: Rental types Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$121

New Listing Fully Renovated, Saltwater Pool, Smart TV’s /WiFi, Covered Parking,

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 4 minutes

Match: Rental types Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$203

Rare opening in March. 5 Min Walk to Beach, Pool

Gulf Gate Estates house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 4 minutes

Match: Rental types Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$761

Lower Prices! Walk to Village, Heated Saltwater Pool

Siesta Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

“Beautiful and clean private home with pool and close to everything!” The home was in walking distance to village and beach. Beautiful and clean home with private pool. The home had everything that we could ask for. We had an outstanding time on our vacation. We will definitely return to this home again.

Responds fast! avg. 4 minutes

Match: Rental types Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$196

Responds fast! avg. 4 minutes

Match: Rental types Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$340

Responds fast! avg. 4 minutes

Match: Rental types Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$249

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

Paradise 3 Bedroom Pool Home Close to Siesta Key Beach and IMG Academy

Braden River house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 9 minutes

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

2 of 3 filters match

Price per night from

$373

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

2 of 3 filters match

Price per night from

$573

Glorious Daze 4bedroom/4bath beachfront home with golf cart & elevator!

Holmes Beach house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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

2 of 3 filters match

Price per night from

$1,374

Castaway Cottage

Holmes Beach house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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

2 of 3 filters match

Price per night from

$390

Remodeled 4BR Pool Home / Golf View/Near Beaches

South Bradenton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

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

2 of 3 filters match

Price per night from

$516

Coastal Paradise! 5 mi to beaches! Heated Pool! Sleep up to 14

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

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

2 of 3 filters match

Price per night from

$1,254

FantaSea

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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

2 of 3 filters match

Price per night from

$1,489

THE LIDO RESIDENCE

Lido Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

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

2 of 3 filters match

Price per night from

$778

Responds fast! avg. 4 minutes

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

2 of 3 filters match

Price per night from

$103

Chinaberry 911 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

2 of 3 filters match

Price per night from

$171

Buttonwood 467 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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

2 of 3 filters match

Price per night from

$290

Chinaberry 424 at Midnight Cove Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

2 of 3 filters match

Price per night from

$264

Doveplum 121 at Midnight Cove Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

2 of 3 filters match

Price per night from

$296

Firethorn 512 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

2 of 3 filters match

Price per night from

$142

Doveplum 112 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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

2 of 3 filters match

Price per night from

$629

Firethorn 613 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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

2 of 3 filters match

Price per night from

$142

Viewing 38 of 644
rentals in Longboat Key

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