Houses Longboat Key

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665 houses

Gorgeous views,spectacular home!

Anna Maria house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

“Majestic Views” Our family loved our visit to Anna Maria. The house is gorgeous and spacious. My kids enjoyed the pool and eating outside. We hope to return in the near future.

Match: Rental types Private outdoor pool (heated) Pool or snooker table

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Price per night from

$631

A Wonderful Pool House on a lake full of wildlife.

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Location location” Great house convincent , clean , close to everything

Match: Rental types Private outdoor pool (heated) Pool or snooker table

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Price per night from

$121

"Island Oasis" A single family North end canal home with pool

Anna Maria house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (heated) Pool or snooker table

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Price per night from

$745

Anna Maria Beach Serenity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

Match: Rental types Private outdoor pool (heated) Pool or snooker table

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Price per night from

$950

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4 Bedroom with Gulf View Siesta Key FL Beach Fun

Siesta Key apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“Fantastic Location and Beautiful Accomodations” Our daughters and their families stayed here in February. The condo was everything we expected and more. It has a breathtaking view of the Gulf from the screened in lani which runs the width of the unit. The four bedrooms were perfect for our group of nine and the kitchen / dining area was well stocked with appliances , pots & pans , dishes , glassware , etc. Condo has easy access to heated pool and ample parking. Owner made the rental process smooth as silk , and we all felt right at home as soon as we had checked in. Right across street from world famous Siesta Beach. Would highly recommend.

2 of 3 match: Rental types, Private outdoor pool (heated), Pool or snooker table

2 of 3 filters match

Price per night from

$515

Family Reunion Villa on Anna Maria Island, Florida

Bradenton Beach villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

2 of 3 match: Rental types, Private outdoor pool (heated), Pool or snooker table

2 of 3 filters match

Price per night from

$574

2 of 3 match: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$574

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

Holmes Beach house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$1,377

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: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$372

Castaway Cottage

Holmes Beach house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Pool or snooker table, 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: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$516

THE LIDO RESIDENCE

Lido Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

2 of 3 match: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$778

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: Pool or snooker table, 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: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$1,489

Captiva Paradise Home close to IMG Academy & Siesta Key Beach

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 9 minutes

2 of 3 match: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$373

Anna Maria Islands best location Heated pool Best prices!

Anna Maria Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$861

Hibiscus Hideaway Condo Walk to Historic Bridge St

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 39 minutes

2 of 3 match: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$298

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: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$831

Anna Maria Island Beach Palace

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$594

Anna Maria Island Edgewater Bungalow

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$298

Anna Maria Island Sun's Up A

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$498

Anna Maria Island Surfside Bungalow

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$355

Anna Maria Island Sun's Up B

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$479

Zuva Sands

Siesta Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$252

Responds fast! avg. 3 hours 41 minutes

2 of 3 match: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$102

Siesta Key Waterfront Estate heated Pool Privacy!

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

2 of 3 match: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$716

2 of 3 match: Private outdoor pool (heated), Rental types, Pool or snooker table

2 of 3 filters match

Price per night from

$310

The Pink Riverhouse-

Ellenton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Private outdoor pool (heated), Rental types, Pool or snooker table

2 of 3 filters match

Price per night from

$689

Luxury Resort Sleeps 26!

Palma Sola house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 26

Responds fast! avg. 3 hours 39 minutes

2 of 3 match: Private outdoor pool (heated), Rental types, Pool or snooker table

2 of 3 filters match

Price per night from

$2,288

2 of 3 match: Private outdoor pool (heated), Rental types, Pool or snooker table

2 of 3 filters match

Price per night from

$344

Beautiful Sunkst Cottage Bradenton Beach - AMI-Tropical Setting - Heated Pool

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

2 of 3 match: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$517

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

2 of 3 match: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$1,001

2 of 3 match: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$230

Stunning 2,550 Sq.ft House, FL

Bradenton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$286

Another Day in Paradise

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 1 minutes

2 of 3 match: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$545

NEAR IMG ACADEMY AND SIESTA KEY BEACH PARADISE

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 9 minutes

2 of 3 match: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$431

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

2 of 3 match: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$373

Dream beach, pool/spa retreat!

Siesta Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

2 of 3 match: Pool or snooker table, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$345

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rentals in Longboat Key

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