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

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$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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$630

AMI Beach Shack

Bradenton Beach townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 7 minutes

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$248

Secure, Cozy & Cute Private Sleeping Studio for 2

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$234

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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$196

Fanta-Sea 49: By Beachside Management

Siesta Key house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

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$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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$115

Sarasota Downtown, Best Location For Your Vacation !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Responds fast! avg. 2 hours 9 minutes

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$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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$630

AMI Tree House

Bradenton Beach cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 7 minutes

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$241

Living the Dream - Mermaid: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$343

The Treehouse

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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$401

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$229

Cape Aqua

Siesta Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Great place, super location” We thoroughly enjoyed our stay at your home. It was very spacious, clean and inviting. We had everything we needed and the location is wonderful. Thanks and we would definitly recommend your home to others

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$192

Sarasota Apartment in Downtown !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

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$189

Sarasota Downtown All Inclusive Town house !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

Responds fast! avg. 2 hours 9 minutes

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$189

Tiny House Siesta - Yellow Lifeguard Stand Tiny House

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$422

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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$500

Downtown Sarasota Historic Burns Court Adorable Bungalow

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$295

Living the Dream - Starfish: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$343

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

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$482

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

Downtown Sarasota Townhouse in Historic Center !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

Responds fast! avg. 2 hours 9 minutes

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$189

“Charming studio in lovely quiet neighborhood with fenced in private outside area.” This studio has everything you'll need. It's located in a beautiful neighborhood, great for walking. There's a small park just down the road a couple of blocks where you can sit and watch the amazing sun sets or just enjoy watching the boats ride by. The owners are very nice and have a few fur babies of their own, so they may allow you to bring your doggie,too! Sue/Dawn......thank you!!!! I hope to return & stay again.

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$229

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$344

#7 Loft Apartment in Historic District Downtown Sarasota

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$305

Stunning & Bright Sarasota Home

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$395

Banana Cabana: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$240

Living the Dream - Pink Flamingo: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$320

Edgemere

Siesta Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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$267

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

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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$516

Lovely Siesta Key house with heated pool - A block away from Siesta beach!

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$492

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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$126

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

Bradenton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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$281

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$108

The Corner Retreat

Bradenton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$182

Last Mango

Holmes Beach condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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$202

Viewing 38 of 640
rentals in Longboat Key

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