Houses Longboat Key

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349 houses

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

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Pool or snooker table Trampoline

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Price per night from

$287

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

2 of 3 filters match

Price per night from

$344

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

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Price per night from

$310

Luxury Resort Sleeps 26!

Palma Sola house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 26

Responds fast! avg. 3 hours 39 minutes

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

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Price per night from

$2,289

Anna Maria Beach Serenity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

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

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Price per night from

$950

The Pink Riverhouse-

Ellenton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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

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Price per night from

$687

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.

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

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Price per night from

$630

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

2 of 3 match: Trampoline, Rental types, 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

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

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Price per night from

$745

Newly renovated beach house near AMI free trolley stop with Private pool

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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

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Price per night from

$561

Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$489

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 3 filters match

Price per night from

$489

Pineapple at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$489

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, Trampoline, Pool or snooker table

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Price per night from

$401

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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

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Price per night from

$229

Orchid at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$489

Split Leaf at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$489

Coconut at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$489

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, Trampoline, Pool or snooker table

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Price per night from

$401

St.Armands Circle condo ( Kingston Arms )

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 25 minutes

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

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Price per night from

$258

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

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

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Price per night from

$161

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$436

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, Trampoline, Pool or snooker table

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Price per night from

$114

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, Trampoline, Pool or snooker table

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Price per night from

$182

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, Trampoline, Pool or snooker table

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Price per night from

$903

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, Trampoline, Pool or snooker table

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Price per night from

$138

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

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

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

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Price per night from

$178

Bird of Paradise at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$489

Beachfront Condo Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great place” We couldn't have a better time. The condo had everything you could possibly need for cooking, or going to the pool and beach. The condo is a 3 minute walk to the beach, and the weather was perfect. Village is a 5 minute drive and the restaurants were perfect for a family. Definitely coming back!

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

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Price per night from

$453

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.

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

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Price per night from

$514

“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

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

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Price per night from

$245

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

1 of 3 filters match

Price per night from

$117

Family Reunion Villa on Anna Maria Island, Florida

Bradenton Beach villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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

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Price per night from

$573

*** SUPER SPECIAL RATES at Harbor Towers ***

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 56 minutes

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

1 of 3 filters match

Price per night from

$114

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

Longboat Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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

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Price per night from

$745

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

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Price per night from

$148

Responds fast! avg. 11 minutes

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

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Price per night from

$132

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

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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

1 of 3 filters match

Price per night from

$516

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rentals in Longboat Key

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