Vacation Rentals & Apartments in Longboat Key

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AnnaMariaIsland a Paradise. MINUMIM RENTAL 2 WEEKS

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 22 minutes

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Price per night from

$196

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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$115

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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$630

Luxurious 2 BR Condo-Short Walk to Siesta Beach/1 Small Dog (25 lbs Max) Allowed

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“a fine 2 weeks in Siesta” charming property, that was comfortable for four. The unit was very clean and fresh upon arrival. The neighbours were friendly and the overall property well kept. Siesta Key is a quiet community with usual shopping amenities over the causeway. This property was a brief 10 minute walk to the beach. Would we stay again, yes.

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$165

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$229

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

$999

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

Downtown Sarasota Historic Burns Court Adorable Bungalow

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$295

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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$272

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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$287

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$344

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

$516

Light and Airy and Private, Great Location

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$229

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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$107

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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$563

Lovely gulf view! Walk to beach!

Bradenton Beach townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 39 minutes

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Price per night from

$185

Serendipity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,260

White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$631

Palm Haven Beach Side Villa

Holmes Beach villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 39 minutes

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$164

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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One Bedroom in Historic Burns Square District downtown

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$315

#7 Loft Apartment in Historic District Downtown Sarasota

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$305

Charming Private Studio in Historic Downtown Area

Sarasota studio

  • Studio
  • 1 bathroom
  • sleeps 3

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Price per night from

$258

Secure, Cozy & Cute Private Sleeping Studio for 2

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$234

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

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 - Red Lifeguard Stand

Siesta Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$443

Tiny House Siesta - Tiny Aqua Oasis- Tiny House that sleeps 6 comfortably

Siesta Key hotel apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$444

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

Gorgeous Waterfront Apartment Steps From 100Ft Fishing Dock And Tiki.

Palmetto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$167

Luxury Modern Oasis in Heart of Sarasota

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$1,032

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

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

$343

The Hideaway: 4/2 W Heated Pool and Outdoor Spaces, 10 mins to Sarasota Beach

Gulf Gate Estates house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$373

Blue Heron Inn: 1/1 Spacious Apartment, 15 mins to beaches, pet friendly

Oneco apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$127

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Price per night from

$167

Lazy Manatee Apt: 15 mins to beach and SRQ airport - pet friendly!

Oneco apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$144

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rentals in Longboat Key

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