Vacation Rentals & Apartments in Longboat Key

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52 apartments

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$437

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

Longboat Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$748

Great rentals within 20 miles that match your search

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

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$403

River Strand Golf and Country Club Resort

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$230

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

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$161

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

$633

St.Armands Circle condo ( Kingston Arms )

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 25 minutes

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$259

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.

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Price per night from

$516

Clean comfort in Sarasota-book now for comfort

Sarasota caravan/mobile home

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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Price per night from

$135

“Anniversary Trip” Had a wonderful time at LA Siesta Condominiums for our anniversary vacation. Beautifully furnished and do close to the best beach in the USA

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Price per night from

$246

A Paradise for Golfers and Tennis players

Bradenton apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 27 minutes

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Price per night from

$140

Family Reunion Villa on Anna Maria Island, Florida

Bradenton Beach villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$575

Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$110

Gulf and Bay Club 3bdrm “E” Luxury END CORNER Unit - RIGHT ON BEACH

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$906

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Price per night from

$345

*** SUPER SPECIAL RATES at Harbor Towers ***

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 56 minutes

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Price per night from

$114

NEW! Luxurious Coastal Condo 5 minutes to Anna Maria Island

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$403

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$230

3 bedrooms luxurious home,2 full bath, swimming pool, fully remodeled,pool table

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$546

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Price per night from

$311

The Pink Riverhouse-

Ellenton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$690

Bird of Paradise at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$491

Split Leaf at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$491

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$491

Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$491

Orchid at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$491

Pineapple at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$491

Coconut at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$491

Indulge in a spacious 4-bedroom rental with private pool and beach access!

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$978

Discover the perfect beachfront getaway with a private pool & hot tub.

Siesta Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$857

Experience the luxury of private beach living with TWO heated pools!

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,156

Outdoor Oasis Awaits! Your perfect vacation spot just steps away from the beach

Anna Maria Island house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$1,024

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Price per night from

$794

Modern home with Private pool, walk to the beach, Putting green & Ping pong

Anna Maria house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$914

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Price per night from

$1,035

Beachfront Condo Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great place” We couldn't have a better time. The condo had everything you could possibly need for cooking, or going to the pool and beach. The condo is a 3 minute walk to the beach, and the weather was perfect. Village is a 5 minute drive and the restaurants were perfect for a family. Definitely coming back!

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Price per night from

$455

River Strand Luxury Condo-Tennis & Golf Community

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$87

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

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Price per night from

$121

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rentals in Longboat Key

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