Houses Longboat Key

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861 houses

Luxury Resort Sleeps 26!

Palma Sola house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 26

Responds fast! avg. 3 hours 39 minutes

Match: Rental types Freezer Pool or snooker table Staffed property

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Price per night from

$2,289

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Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Rental types, Freezer, Pool or snooker table, Staffed property

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Price per night from

$230

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

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

3 of 4 match: Rental types, Freezer, Pool or snooker table, Staffed property

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Price per night from

$178

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

3 of 4 match: Rental types, Freezer, Pool or snooker table, Staffed property

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Price per night from

$114

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Rental types, Freezer, Pool or snooker table, Staffed property

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Price per night from

$435

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

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

3 of 4 match: Rental types, Freezer, Pool or snooker table, Staffed property

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Price per night from

$903

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

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 56 minutes

3 of 4 match: Rental types, Freezer, Pool or snooker table, Staffed property

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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

3 of 4 match: Rental types, Freezer, Pool or snooker table, Staffed property

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Price per night from

$746

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!

3 of 4 match: Rental types, Freezer, Pool or snooker table, Staffed property

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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.

3 of 4 match: Rental types, Freezer, Pool or snooker table, Staffed property

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Price per night from

$514

Responds fast! avg. 11 minutes

3 of 4 match: Rental types, Freezer, Pool or snooker table, Staffed property

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Price per night from

$132

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

3 of 4 match: Rental types, Freezer, Pool or snooker table, Staffed property

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Price per night from

$117

The Pink Riverhouse-

Ellenton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Rental types, Freezer, Pool or snooker table

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Price per night from

$689

3 of 4 match: Staffed property, Rental types, Freezer, Pool or snooker table

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Price per night from

$344

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Rental types, Staffed property, Freezer, 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

2 of 4 match: Rental types, Staffed property, Freezer, Pool or snooker table

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Price per night from

$490

Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Rental types, Staffed property, Freezer, Pool or snooker table

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Price per night from

$489

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

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Rental types, Freezer, Pool or snooker table

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Price per night from

$563

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

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Rental types, Freezer, Pool or snooker table

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Price per night from

$287

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.

3 of 4 match: Staffed property, Rental types, Freezer, 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

3 of 4 match: Staffed property, Rental types, Freezer, 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

3 of 4 match: Staffed property, Rental types, Freezer, Pool or snooker table

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Price per night from

$745

NEW! Luxurious Coastal Condo 5 minutes to Anna Maria Island

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Staffed property, Freezer, Pool or snooker table

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Price per night from

$402

Orchid at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Rental types, Staffed property, Freezer, 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

2 of 4 match: Rental types, Staffed property, Freezer, 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

2 of 4 match: Rental types, Staffed property, Freezer, Pool or snooker table

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Price per night from

$489

The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Pool or snooker table, Rental types, Freezer, Staffed property

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Price per night from

$345

🏝Paradise on the Sarasota Bay, Close to Gulf Beaches🏝 (Sarasota)

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 4 match: Rental types, Pool or snooker table, Freezer, Staffed property

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Price per night from

$194

Buttonwood 442

Gulf Gate Estates condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Pool or snooker table, Freezer, Staffed property

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Price per night from

$290

Sarasota Downtown, Best Location For Your Vacation !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Responds fast! avg. 1 hour 46 minutes

2 of 4 match: Rental types, Pool or snooker table, Freezer, Staffed property

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Price per night from

$194

Bird of Paradise at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Rental types, Staffed property, Freezer, Pool or snooker table

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Price per night from

$490

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

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 4 match: Rental types, Staffed property, Freezer, Pool or snooker table

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Price per night from

$401

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

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 4 match: Rental types, Staffed property, Freezer, Pool or snooker table

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Price per night from

$161

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

Siesta Key apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Staffed property, Freezer, Pool or snooker table

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Price per night from

$182

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

3 of 4 match: Pool or snooker table, Rental types, Freezer, Staffed property

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Price per night from

$149

Spacious Apt. #1 Historic Walkable Downtown, between Siesta & Lido Beach

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Rental types, Pool or snooker table, Freezer, Staffed property

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Price per night from

$482

Secure, Cozy & Cute Private Sleeping Studio for 2

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 4 match: Rental types, Pool or snooker table, Freezer, Staffed property

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Price per night from

$234

Banana Cabana: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Pool or snooker table, Freezer, Staffed property

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Price per night from

$240

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rentals in Longboat Key

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