Houses Longboat Key

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504 houses

Off the Hook: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Rental types Shared outdoor pool (heated) Table tennis

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Price per night from

$515

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4 minute flip flop walk to the beach! Starfish 2/2

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Table tennis, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$339

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

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Shared outdoor pool (heated), Table tennis

2 of 3 filters match

Price per night from

$402

Bird of Paradise at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Shared outdoor pool (heated), Table tennis

2 of 3 filters match

Price per night from

$490

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

Siesta Key apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Shared outdoor pool (heated), Table tennis

2 of 3 filters match

Price per night from

$183

Beach Walk: By Beachside Management

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Shared outdoor pool (heated), Table tennis

2 of 3 filters match

Price per night from

$515

Waterview Oasis Retreat, minutes to Anna Maria Island and IMG

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Shared outdoor pool (heated), Table tennis

2 of 3 filters match

Price per night from

$109

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

2 of 3 match: Rental types, Shared outdoor pool (heated), Table tennis

2 of 3 filters match

Price per night from

$138

A Somewhere Is Here - Changes in Attitude: By Beachside Management

Siesta Key apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

2 of 3 match: Rental types, Shared outdoor pool (heated), Table tennis

2 of 3 filters match

Price per night from

$411

A Somewhere is Here - Changes in Latitude: By Beachside Management

Siesta Key apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

2 of 3 match: Rental types, Shared outdoor pool (heated), Table tennis

2 of 3 filters match

Price per night from

$457

Amazing Village Cottage! Walk to Whitney Beach!

Longboat Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Table tennis, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$394

Private Retreat on Siesta Dr

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 49 minutes

2 of 3 match: Table tennis, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$516

St Armand's Private Home on Jackson Drive

Lido Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Table tennis, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$382

"Lido Lookout" Beach Paradise Private Home on Lido Key

Lido Key house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

2 of 3 match: Table tennis, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$2,977

Beach Bliss

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

2 of 3 match: Table tennis, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$1,145

Limefish

Holmes Beach house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Table tennis, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$2,061

“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, Shared outdoor pool (heated), Table tennis

2 of 3 filters match

Price per night from

$246

Florida Ocean Front Condo

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Shared outdoor pool (heated), Table tennis

2 of 3 filters match

Price per night from

$623

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

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 56 minutes

2 of 3 match: Rental types, Shared outdoor pool (heated), Table tennis

2 of 3 filters match

Price per night from

$114

Beach to Bay Tropical Oasis! 2Bed/2Bath Longboat Key Condo

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Shared outdoor pool (heated), Table tennis

2 of 3 filters match

Price per night from

$153

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, Shared outdoor pool (heated), Table tennis

2 of 3 filters match

Price per night from

$117

2 of 3 match: Rental types, Shared outdoor pool (heated), Table tennis

2 of 3 filters match

Price per night from

$148

Responds fast! avg. 11 minutes

2 of 3 match: Rental types, Shared outdoor pool (heated), Table tennis

2 of 3 filters match

Price per night from

$132

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!

2 of 3 match: Rental types, Shared outdoor pool (heated), Table tennis

2 of 3 filters match

Price per night from

$453

Great location, quiet, peaceful, and comfortable

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Table tennis, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$46

Super Cute Cottage--Private--Walk/Bike to Beach

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Shared outdoor pool (heated), Rental types, Table tennis

2 of 3 filters match

Price per night from

$258

2 bedroom Condo Bay Oaks Siesta Key

Sarasota condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

1 of 3 match: Rental types, Table tennis, Shared outdoor pool (heated)

1 of 3 filters match

Price per night from

$574

Direct Beachfront 2 BR Condo on Florida’S Beautiful Gulf Coast!

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Rental types, Table tennis, Shared outdoor pool (heated)

1 of 3 filters match

Price per night from

$430

Stunning 2,550 Sq.ft House, FL

Bradenton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Table tennis, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$286

1 bedroom single story ocean view

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Table tennis, Shared outdoor pool (heated)

1 of 3 filters match

Price per night from

$360

2 bedroom Florida condo unit 13 at family friendly resort

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Table tennis, Shared outdoor pool (heated)

1 of 3 filters match

Price per night from

$426

“Great stay in Sarasota” My husband and our two daughters spent a wonderful four days in Sarasota. The townhome we stayed in was beautiful and had all the amenities we needed. We spent every day at the beach and relaxed at the townhome in the evenings. We would definitely stay here again and have recommended this place to our family and friends. Thanks Louie!

Responds fast! avg. 2 hours 32 minutes

1 of 3 match: Rental types, Table tennis, Shared outdoor pool (heated)

1 of 3 filters match

Price per night from

$435

1 bedroom single story condo near pool

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Table tennis, Shared outdoor pool (heated)

1 of 3 filters match

Price per night from

$295

2 bedroom poolside condo steps from ocean beach and dock on bay

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Table tennis, Shared outdoor pool (heated)

1 of 3 filters match

Price per night from

$426

Siesta Key Beach Condo, 2Br/2Ba Direct Beach Front

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“What a great view” We usually rent a house one block from the main Siesta Key beach area. This year friends rented the house and my husband and I stayed in this condo for a week. Loved the view of the beach from the living room! Loved the lani! Location was great. Pool was massive compared to our usual house pool, however we did have to walk thru parking lot to get there. The noise from the hall was annoying. And I did miss my temperpedic mattress, but had a great relaxing time.

2 of 3 match: Table tennis, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$328

Luxury Waterfront Views/Pool/1400sf/2 min to Beach

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 32 minutes

1 of 3 match: Rental types, Table tennis, Shared outdoor pool (heated)

1 of 3 filters match

Price per night from

$340

Siesta Key Gulf View Condo

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 33 minutes

1 of 3 match: Rental types, Table tennis, Shared outdoor pool (heated)

1 of 3 filters match

Price per night from

$448

Siesta Key vaca rental

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 3 match: Rental types, Table tennis, Shared outdoor pool (heated)

1 of 3 filters match

Price per night from

$230

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rentals in Longboat Key

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