Vacation Rentals & Apartments in Longboat Key

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Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Golf within 30mins drive

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Price per night from

$436

Zilli Ocean Front 101

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Golf within 30mins drive

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Price per night from

$286

ZILLI VILLA

Longboat Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Golf within 30mins drive

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Price per night from

$488

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$430

180 Panoramic beach View and amazing Sunset.

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Golf within 30mins drive

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Price per night from

$457

Amazing beachfront View & balcony on Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$434

Seaplace Condo - 1975 GMD 104

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$192

Zilli Ocean Front 201 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Golf within 30mins drive

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Price per night from

$298

Zilli Ocean Front 202 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Golf within 30mins drive

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Price per night from

$297

Zilli Tower 503

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Golf within 30mins drive

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Price per night from

$343

Sea~N~Blue

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$402

Beachplace Building 3 unit 302

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$187

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

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$153

Great rentals within 20 miles that match your search

Newly Remodeled Spacious Loft in Sarasota!

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$295

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

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Golf within 30mins drive

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Price per night from

$517

Beautiful Crescent Beach on Siesta Key One of the

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$301

FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN CONDO!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Golf within 30mins drive

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Price per night from

$272

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Golf within 30mins drive

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Price per night from

$1,001

Monthly Rental, 2 bed, 2 bath, Ocean view.

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Golf within 30mins drive

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Price per night from

$115

Shorewalk Condo ED near the Beaches Anna Maria Island, Longboat Key, IMG, Shops

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$402

3BR/4BA TOWNHOUSE - POOL VIEW PARADISE - PRIVATE BEACH ACCESS

Siesta Key townhouse

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 38 minutes

Match: Golf within 30mins drive

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Price per night from

$431

Tara Golf & Country Club Condo

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful, peaceful location and beautiful condo.” This condo is wonderful and has everything anyone would want or need for a wonderful stay. We loved the property and the owners. It is located in a private championship golf course community and is just across the street from all the amenities. The amenities include tennis, pool, workout room, and of course golf at its best. There is a wonderful grill room and beautiful dining room facing the driving range. Very close to a hugh shopping area and enclosed mall. Very convenient to travel anywhere from here. Very nice rental in a wonderful area.

Match: Golf within 30mins drive

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Price per night from

$144

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Price per night from

$285

Ideal Retreat next to USA's #1 Beach—Siesta Key

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$161

River Strand Luxury Condo-Tennis & Golf Community

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Golf within 30mins drive

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Price per night from

$86

Lido Sunshine M

Lido Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$183

Piece of Paradise on Beautiful Anna Maria Island VRC 20-000087

Holmes Beach villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$148

2-Unit Beach to Bay Cottage...NOT Grandma's place!...100 feet to beach!

Bradenton Beach cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Best home away from home at the beach.” I spent a lot of time searching for a bungalow at the beach and my expectations were surpassed when I opened the door! The owners were thoughtful in design, layout and furnishings to provide a laid back experience at the beach. I wished I could have stayed forever - it was that nice. I especially enjoyed the fully stocked kitchen which included colorful dishes to match the colorful walls and great blue floor! Best of all - location - you can walk everywhere as you are right in the historic Bridge Street neighborhood.

Match: Golf within 30mins drive

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Price per night from

$246

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Golf within 30mins drive

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Price per night from

$206

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.

Match: Golf within 30mins drive

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Price per night from

$631

Jacaranda Artist Retreat

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Golf within 30mins drive

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Price per night from

$219

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!

Match: Golf within 30mins drive

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Price per night from

$273

4 Bedroom with Gulf View Siesta Key FL Beach Fun

Siesta Key apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“Fantastic Location and Beautiful Accomodations” Our daughters and their families stayed here in February. The condo was everything we expected and more. It has a breathtaking view of the Gulf from the screened in lani which runs the width of the unit. The four bedrooms were perfect for our group of nine and the kitchen / dining area was well stocked with appliances , pots & pans , dishes , glassware , etc. Condo has easy access to heated pool and ample parking. Owner made the rental process smooth as silk , and we all felt right at home as soon as we had checked in. Right across street from world famous Siesta Beach. Would highly recommend.

Match: Golf within 30mins drive

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Price per night from

$516

ISLAND TOWNHOUSE - 200 Steps to the BEACH

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 49 minutes

Match: Golf within 30mins drive

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Price per night from

$207

Match: Golf within 30mins drive

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Price per night from

$230

Clean comfort in Sarasota-book now for comfort

Sarasota caravan/mobile home

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$135

GULF FRONT ON #1 Beach! Siesta Dunes (by owner)

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Perfect, Perfect, Perfect” Nice condo with everything close by! Owners were great to deal with and as stated it would be . We plan on visiting again and would recommend this place to anyone.

Match: Golf within 30mins drive

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Price per night from

$272

A Wonderful Pool House on a lake full of wildlife.

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Location location” Great house convincent , clean , close to everything

Match: Golf within 30mins drive

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Price per night from

$122

Viewing 38 of 212
rentals in Longboat Key

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