Houses Longboat Key

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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 Safe 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 Safe Pool or snooker table

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Price per night from

$122

Match: Rental types Safe Pool or snooker table

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Price per night from

$345

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

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Safe Pool or snooker table

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Price per night from

$287

Luxury Resort Sleeps 26!

Palma Sola house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 26

Responds fast! avg. 3 hours 39 minutes

Match: Rental types Safe Pool or snooker table

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Price per night from

$2,294

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St.Armands Circle condo ( Kingston Arms )

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 25 minutes

2 of 3 match: Rental types, Safe, Pool or snooker table

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Price per night from

$259

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Safe, Pool or snooker table

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Price per night from

$436

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

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

2 of 3 match: Rental types, Safe, Pool or snooker table

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Price per night from

$178

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, Safe, Pool or snooker table

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Price per night from

$516

“Anniversary Trip” Had a wonderful time at LA Siesta Condominiums for our anniversary vacation. Beautifully furnished and do close to the best beach in the USA

2 of 3 match: Rental types, Safe, Pool or snooker table

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Price per night from

$246

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

Longboat Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Safe, Pool or snooker table

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Price per night from

$746

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

2 of 3 match: Rental types, Safe, Pool or snooker table

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Price per night from

$117

2 of 3 match: Rental types, Safe, Pool or snooker table

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Price per night from

$148

2 of 3 match: Safe, Rental types, Pool or snooker table

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Price per night from

$310

The Pink Riverhouse-

Ellenton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Safe, Rental types, Pool or snooker table

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Price per night from

$689

Anna Maria Beach Serenity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Safe, Rental types, Pool or snooker table

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Price per night from

$951

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

Anna Maria house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Safe, Rental types, Pool or snooker table

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Price per night from

$746

Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Safe, Pool or snooker table

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Price per night from

$490

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Safe, Pool or snooker table

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Price per night from

$490

Pineapple at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Safe, Pool or snooker table

1 of 3 filters match

Price per night from

$490

NEW! Luxurious Coastal Condo 5 minutes to Anna Maria Island

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Safe, Pool or snooker table

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Price per night from

$402

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 3 match: Rental types, Safe, Pool or snooker table

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Price per night from

$230

Orchid at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Safe, Pool or snooker table

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Price per night from

$490

Coconut at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Safe, Pool or snooker table

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Price per night from

$490

Split Leaf at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Safe, Pool or snooker table

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Price per night from

$490

TROPICCAL, 4 min from the beaches! Meticulously cleaned and sanitized!

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

“Lovely home in an awesome location!” Literally a minute's drive from the beach, this very clean and welcoming home is also convenient to great restaurants and shopping opportunities. It really is in a perfect location, especially considering the affordable price. Walking to restaurants and a rental shop is easy thanks to the sidewalk on Cortes. We even enjoyed a morning run to the beach - biking to the beach would also be a great option (3.5 mi one way.) The home might appear small at first, but we fit 6 comfortably, including 4 teenagers! The best part is the lovely décor that greets you after a long day at the beach or running around. Two thumbs up!

Responds fast! avg. 2 hours 33 minutes

2 of 3 match: Pool or snooker table, Rental types, Safe

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Price per night from

$144

Shorewalk Condo ED near the Beaches Anna Maria Island, Longboat Key, IMG, Shops

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Rental types, Safe, Pool or snooker table

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Price per night from

$402

Ideal Retreat next to USA's #1 Beach—Siesta Key

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Rental types, Safe, Pool or snooker table

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Price per night from

$161

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 3 match: Rental types, Safe, Pool or snooker table

1 of 3 filters match

Price per night from

$114

Gulf and Bay Club 3bdrm “E” Luxury END CORNER Unit - RIGHT ON BEACH

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 3 match: Rental types, Safe, Pool or snooker table

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Price per night from

$904

Bird of Paradise at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Safe, Pool or snooker table

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Price per night from

$490

Modern Lakerfront Condo! 2x Pools~WiFi~Lanai. By IMG~Beaches~Restaurants~AMI~SRQ

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 11 minutes

1 of 3 match: Rental types, Safe, Pool or snooker table

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Price per night from

$138

Siesta Key Beach : 2 Bedroom, 3 Beds, 3 Bathroom Duplex & Heated Pool

Siesta Key apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Safe, Pool or snooker table

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Price per night from

$183

#1 EXCLUSIVE Siesta Key Beach House /3 payments

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Pool or snooker table, Rental types, Safe

2 of 3 filters match

Price per night from

$259

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, Safe

2 of 3 filters match

Price per night from

$717

2 of 3 match: Pool or snooker table, Rental types, Safe

2 of 3 filters match

Price per night from

$183

ISLAND TOWNHOUSE - 200 Steps to the BEACH

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 49 minutes

2 of 3 match: Pool or snooker table, Rental types, Safe

2 of 3 filters match

Price per night from

$207

The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Pool or snooker table, Rental types, Safe

2 of 3 filters match

Price per night from

$345

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