Houses Longboat Key

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856 houses

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$149

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Private Beach Access - Home away from Home - 2 BR 2 BA - Furnished Condo

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$177

Siesta Key Townhouse across from Pristine Sands of Siesta Key 2B/2B sleeps 6

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Fantastic week in Siesta Key” The townhouse was fantastic and fully equipped with everything we needed for a very comfortable week. The location was outstanding - right across from the beach and the free trolley to the Village stopped right outside. The garage had everything the family needed to take to the beach and we met some lovely people around the pool. Thank you Michelle for your hospitality - we hope to be back soon.

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

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Price per night from

$189

The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

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Price per night from

$343

Luxury Resort Sleeps 26!

Palma Sola house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 26

Responds fast! avg. 3 hours 39 minutes

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

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Price per night from

$2,289

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

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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

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Price per night from

$193

Sarasota Downtown, Best Location For Your Vacation !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Responds fast! avg. 1 hour 57 minutes

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

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Price per night from

$193

Buttonwood 442

Gulf Gate Estates condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$290

Beautiful house for rent at siesta key beach with pool, theater and game room

Siesta Key house

  • 7 bedrooms
  • 3 bathrooms
  • sleeps 15

Responds fast! avg. 1 hour 59 minutes

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

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Price per night from

$2,840

A Pearl of a Beach Home - now with luxury Saltwater heated pool and hot tub

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Perfect Luxury” Our 5-week stay at this vacation rental was absolutely perfect. The house was everything you could ask for and more. We have stayed in many vacation rentals in the last 20 or so years that we have been coming to anna Maria Island and I have to say this one was right at the top of the list. The kitchen was outfitted with everything you could want. The beds were very comfortable. The neighborhood was nice and quiet. Short walk to the beach. The owners were very nice to deal with and always responded quickly and were very warm and helpful. Definitely can recommend this vacation rental.

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

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Price per night from

$474

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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

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Price per night from

$229

Banana Cabana: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$239

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

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$482

Palm Bay Club - 343: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$286

Secure, Cozy & Cute Private Sleeping Studio for 2

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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

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Price per night from

$234

Manatee River Cottage in Historic Old Town

Palmetto cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

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

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Price per night from

$148

Jamaica Royale #104! Completely renovated, Gulf side, beautiful 2b/2b Condo!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$336

Runaway Bay - Bradenton Beach - Bay View Unit 193

Anna Maria Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Home away from home” This place is an incredible value. It's spacious and comfortable, and we felt right at home. Sarasota Bay is just steps from the back patio, and it's so lovely to sit outside and watch water--so many fish, dolphins, and birds right there. Everything was in good working order and clean upon our arrival. The beach is a quick walk across the street from the complex, and we spent a lot of time at the heated pool. We would love to rent this unit again! PERFECT LOCATION.

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

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Price per night from

$208

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

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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

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

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Price per night from

$434

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

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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

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Price per night from

$899

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

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

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

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Price per night from

$177

Zilli Ocean Front 202 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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

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Price per night from

$307

Jamaica Royale - Beachfront Tower: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$376

Living the Dream - Pink Flamingo: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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

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Price per night from

$319

Ten35 Seaside - North Water View: Residence 506

Siesta Key condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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

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Price per night from

$775

Ten35 Seaside - South Water View: Residence 302

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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

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Price per night from

$604

Ten35 Seaside - Island View: Residence 308

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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

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Price per night from

$547

Ten35 Seaside - Island View: Residence 406

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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

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Price per night from

$558

Crescent Beach Villas - La Perlita: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$273

Ten35 Seaside - Island View: Residence 404

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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

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Price per night from

$547

Living the Dream - Starfish: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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

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Price per night from

$341

Ten35 Seaside - North Water View: Residence 310

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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

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Price per night from

$627

Ten35 Seaside - Island View: Residence 408

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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

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Price per night from

$547

Ten35 Seaside - South Water View: Residence 602

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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

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Price per night from

$684

Ten35 Seaside - Direct Gulf View: Residence 501

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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

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Price per night from

$946

Ten35 Seaside - Island View: Residence 604

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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

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Price per night from

$558

Zilli Tower 503

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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

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Price per night from

$343

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rentals in Longboat Key

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