Vacation Rentals & Apartments in Longboat Key

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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: Golf within 30mins drive Pets allowed

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Price per night from

$224

Beachfront Paradise w/ Private Beach, Dogs Stay Free, Beach in Backyard

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$632

Secure, Cozy & Cute Private Sleeping Studio for 2

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$235

Fanta-Sea 49: By Beachside Management

Siesta Key house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

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Price per night from

$860

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

Sarasota Downtown, Best Location For Your Vacation !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Responds fast! avg. 1 hour 46 minutes

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Price per night from

$194

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.

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Price per night from

$632

Living the Dream - Mermaid: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$344

Beautiful Location On Bay Side, Water View, Pool

Sarasota villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$230

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Price per night from

$230

Sarasota Apartment in Downtown !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 46 minutes

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Price per night from

$190

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$1,001

Sarasota Downtown All Inclusive Town house !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

Responds fast! avg. 1 hour 46 minutes

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Price per night from

$190

Tiny House Siesta - Yellow Lifeguard Stand Tiny House

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$423

Tiny House Siesta - Sand Dollar – A private master loft and open living space

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$448

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 - Starfish: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$344

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

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$484

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

$273

SPECIAL! $650 8/24 - 8/31. PRIME LOCATION AMI DIRECTLY ON BEACH HEATED POOL

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$287

Downtown Sarasota Townhouse in Historic Center !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

Responds fast! avg. 1 hour 46 minutes

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Price per night from

$190

Jacaranda Artist Retreat

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$218

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

$321

Beautiful Sunkst Cottage Bradenton Beach - AMI-Tropical Setting - Heated Pool

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$517

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

$402

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Price per night from

$107

Gorgeous Pool Home. 12 min from the beaches of Anna Maria, IMG

Bradenton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$282

Serendipity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,263

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Price per night from

$108

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Price per night from

$287

Coastal Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$173

Close to Siesta key with hot tub, fire pit and butterfly garden

Gulf Gate Estates guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$193

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

$2,295

Remodeled Exquisite Home. 10 min from the Beaches of Anna Maria Island. 7min IMG

South Bradenton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$344

Beautiful Longboat Key Home!

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 27 minutes

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Price per night from

$517

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

$2,296

Sea Shell Cottage

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Golf within 30mins drive Pets allowed

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Price per night from

$173

Newly remodeled condo on the Bradenton Riverwalk

Bradenton condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Golf within 30mins drive Pets allowed

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Price per night from

$109

Viewing 38 of 315
rentals in Longboat Key

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