Vacation Rentals & Apartments in Longboat Key

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Longboat Key Cedars Beach House-Pet Friendly-2 Minute To The Beach

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

Match: Bicycles available Pets allowed

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Price per night from

$190

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Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Bicycles available

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Price per night from

$436

Florida Ocean Front Condo

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Bicycles available

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Price per night from

$622

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

Longboat Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Bicycles available

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Price per night from

$745

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

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Pets allowed, Bicycles available

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Price per night from

$153

Amazing Village Cottage! Walk to Whitney Beach!

Longboat Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Pets allowed

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Price per night from

$393

Great rentals within 20 miles that match your search

Beautiful Location On Bay Side, Water View, Pool

Sarasota villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Match: Bicycles available Pets allowed

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Price per night from

$229

Serendipity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,260

Siesta Key 2 Bedroom 1 Bath Modern/Contemporary Decor Apartment

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Amazing!” I stayed here with my husband and we had a great time! We were in Orlando visiting family and we decided to arrange some us time. The condo was excellent and very clean! Kathy and her husband were very informative, respond quickly,and available when we needed them. What was great was that we had all beach items available to us and were very useful. We were in close proximity to everything and the beach and restaurants were great! Everyone in the area was very friendly and my husband and I want to definitely come back!

Responds fast! avg. 1 hour 14 minutes

Match: Bicycles available Pets allowed

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Price per night from

$224

Sandy Toes Town Home

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Time in Paradise” We recently had the luck to spend two months in paradise. This condo was comfortably appointed, well stock to meet all our needs, and most importantly in the perfect location. The beach was a short walk to the left and stores and restaurants were just a short walk to the right. We had a great time and enjoyed everything Sarasota, Siesta Key, and this Sandy Toes Condo had to offer. Thanks Mark!

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Price per night from

$272

A Siesta Tropical Retreat - Island Pool Oasis in Village & 2 blocks to Beach

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

“Your best choice for location!” We stayed for 10 lovely days in this home and I have to say It was an even better location than I expected. Everything you could want to do is in walking distance or you can walk to the village (maybe a 3 minute walk)and hop in a free taxi . The house is well appointed and beds are very comfortable. We traveled with a 10 yr.old, 11yr. old , and 15 yr. old my 15 yr. old niece slept in the trundle bed and commented on how comfortable the bed was. In the kitchen you will find a drawer full of menus for the many nearby restaurants and information for water activities. I highly recommend parasailing while your there ! Considering how close everything is the street is very quiet and the owners were great to deal with. Thanks Kathi and Grant!

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Price per night from

$500

Three bedroom house directly on beach with gulf vi

Siesta Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

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Price per night from

$401

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Price per night from

$107

Oceanfront home w/sunset views of Sarasota Bay

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$629

Fanta-Sea 49: By Beachside Management

Siesta Key house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

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Price per night from

$858

Just Minutes from the White Sandy Siesta Beach

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“It was very cozy and comfortable apartment!” We loved to spend our vacation at this place. Really close to the beach, to different restaurants, and all kind of stores.

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Price per night from

$115

LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$161

Sarasota Apartment in Downtown !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 57 minutes

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Price per night from

$189

Serendipity Deux- Beachfront 4 Bed/heated pool/elevator

Anna Maria house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$2,290

Downtown Sarasota Historic Burns Court Adorable Bungalow

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$295

Living the Dream - Mermaid: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$343

Banana Cabana: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Pets allowed

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Price per night from

$240

Living the Dream - Starfish: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Bicycles available Pets allowed

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Price per night from

$343

Living the Dream - Pink Flamingo: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$320

Downtown Sarasota Townhouse in Historic Center !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

Responds fast! avg. 1 hour 57 minutes

Match: Bicycles available Pets allowed

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Price per night from

$189

Sarasota Downtown All Inclusive Town house !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

Responds fast! avg. 1 hour 57 minutes

Match: Bicycles available Pets allowed

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Price per night from

$189

Coral Reef Cutie 2Bedroom Bungalow - 4 Miles to Siesta Key

Osprey cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 14 minutes

Match: Bicycles available Pets allowed

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Price per night from

$132

Luxury Modern Oasis in Heart of Sarasota

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Bicycles available Pets allowed

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Price per night from

$1,030

Beautiful Longboat Key Home!

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 27 minutes

Match: Bicycles available Pets allowed

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Price per night from

$516

White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Bicycles available Pets allowed

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Price per night from

$630

Match: Bicycles available Pets allowed

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Price per night from

$295

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Bicycles available Pets allowed

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Price per night from

$149

Buena Vida: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Bicycles available Pets allowed

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Price per night from

$515

Fanta-Sea 53: By Beachside Management

Siesta Key townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Bicycles available Pets allowed

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Price per night from

$629

Fanta-Sea 55: By Beachside Management

Siesta Key townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Bicycles available Pets allowed

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Price per night from

$160

Match: Bicycles available Pets allowed

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Price per night from

$108

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

Siesta Key apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Bicycles available Pets allowed

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Price per night from

$411

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

Siesta Key apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Bicycles available Pets allowed

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Price per night from

$457

Viewing 38 of 48
rentals in Longboat Key

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