Houses Longboat Key

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394 houses

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

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$562

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

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$287

The Corner Retreat

Bradenton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$183

Luxury Resort Sleeps 26!

Palma Sola house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 26

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$2,288

Aqua Pina: 2 kings, bar area, foosball, sleep 14

Bradenton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$1,098

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Hibiscus Hideaway B - Top Floor Unit

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 39 minutes

2 of 3 match: Safe, Rental types, Games room

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Price per night from

$283

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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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, Games room, Safe

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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, Games room, Safe

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Price per night from

$515

Florida Ocean Front Condo

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Games room, Safe

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Price per night from

$623

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, Games room, Safe

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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, Games room, Safe

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Price per night from

$117

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Price per night from

$148

The Pink Riverhouse-

Ellenton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Safe, Rental types, Games room

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Price per night from

$689

Bay Mariner - Gorgeous water front condo!

Tallevast studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 39 minutes

1 of 3 match: Rental types, Safe, Games room

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Price per night from

$99

Mintfish

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Safe, Rental types, Games room

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Price per night from

$1,145

Las Palmas; by Beachside Management

Siesta Key house

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

2 of 3 match: Safe, Rental types, Games room

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Price per night from

$1,201

Blue Heron Studio / Condo 2 miles from Airport!

Tallevast studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 39 minutes

1 of 3 match: Rental types, Safe, Games room

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Price per night from

$119

Casa Sea Esta Executive Studio / Condo at Sara Cay

Tallevast studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 39 minutes

1 of 3 match: Rental types, Safe, Games room

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Price per night from

$92

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Safe, Games room

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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, Games room

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Price per night from

$490

Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Safe, Games room

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Price per night from

$489

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: Games room, Rental types, Safe

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Price per night from

$144

Orchid at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Safe, Games room

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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, Games room

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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, Games room

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Price per night from

$489

#1 EXCLUSIVE Siesta Key Beach House /3 payments

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Games room, Rental types, Safe

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Price per night from

$259

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Price per night from

$183

Siesta Key Waterfront Estate heated Pool Privacy!

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

2 of 3 match: Games room, Rental types, Safe

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Price per night from

$716

Steps to beach and bay on beautiful Anna Maria Island

Bradenton Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 3 match: Rental types, Safe, Games room

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Price per night from

$101

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, Games room

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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, Games room

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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, Games room

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Price per night from

$138

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, Games room

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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, Safe, Games room

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Price per night from

$182

ISLAND TOWNHOUSE - 200 Steps to the BEACH

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 43 minutes

2 of 3 match: Games room, Rental types, Safe

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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: Games room, Rental types, Safe

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Price per night from

$345

Luxury Modern Oasis in Heart of Sarasota

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Games room, Rental types, Safe

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Price per night from

$1,032

Viewing 38 of 394
rentals in Longboat Key

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