Vacation Rentals & Apartments in Longboat Key

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115 apartments

~ SUPER SPECIAL from $99/night ~ OCEAN FRONT DLX STUDIO

Longboat Key studio

  • Studio
  • 1 bathroom
  • sleeps 3

“Nice Beachfront Location” We stayed there in late June and found it very suitable for our needs. The beach was very accessible. View was awesome. The unit was clean and comfortable for 2 adults.

Responds fast! avg. 1 hour 56 minutes

Match: Sea view

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Price per night from

$193

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Sea view

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Price per night from

$434

ZILLI VILLA

Longboat Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Sea view

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Price per night from

$485

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Sea view

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Price per night from

$428

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

Longboat Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Sea view

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Price per night from

$742

180 Panoramic beach View and amazing Sunset.

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Sea view

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Price per night from

$456

Amazing beachfront View & balcony on Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Sea view

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Price per night from

$433

Seaplace Condo - 1975 GMD 104

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Sea view

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Price per night from

$191

Zilli Ocean Front 201 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Sea view

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Price per night from

$296

Zilli Ocean Front 202 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Sea view

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Price per night from

$307

Sea~N~Blue

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Sea view

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Price per night from

$400

Great rentals within 20 miles that match your search

Beautiful Crescent Beach on Siesta Key One of the

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Sea view

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Price per night from

$299

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

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Sea view

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Price per night from

$286

Amazing Beachfront Condo, Siesta Key,

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Sea view

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Price per night from

$343

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Sea view

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Price per night from

$270

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

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$114

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: Sea view

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Price per night from

$428

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!

Match: Sea view

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Price per night from

$451

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: Sea view

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Price per night from

$512

Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 1 minutes

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Price per night from

$265

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

$400

Enjoy our Beach, Pool and Dock! 100 5-Star Reviews!

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Sea view

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Price per night from

$741

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Price per night from

$143

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Price per night from

$283

Lido Sunshine M

Lido Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Sea view

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Price per night from

$182

Siesta Key - 2bdrm on the beach - amazing views!!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Escape from reality” We had an amazing vacation. Accommodations were great and very comfortable. Breakfast on the lanai and sunset fishing on the beach were 2 of our families favorite things to do. You also have the bay right behind you where you can kayak or paddle board. The community was quiet which was prefect for our getaway. We will definitely be staying here again.

Match: Sea view

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Price per night from

$599

Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Sea view

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Price per night from

$109

Oceanfront home w/sunset views of Sarasota Bay

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Sea view

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Price per night from

$627

Renovated Beach Front 2BR/2BA Condo, Steps to beach, Gulf of Mexico Views

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Sea view

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Price per night from

$276

Family Reunion Villa on Anna Maria Island, Florida

Bradenton Beach villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Sea view

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Price per night from

$571

Another Day in Paradise

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 1 minutes

Match: Sea view

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Price per night from

$542

Cheers to this 2 BR Gulf-front/Intercoastal Endless Summer Beach Retreat!

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 52 minutes

Match: Sea view

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Price per night from

$351

Casey Key 1-Bedroom Dockside Villa #3

Nokomis villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Sea view

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Price per night from

$229

Casey Key 2-Bed Dockside Penthouse

Nokomis penthouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Sea view

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Price per night from

$205

Near Img And Siesta Key Beach Paradise Home

Oneco house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Sea view

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Price per night from

$360

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

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Sea view

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Price per night from

$899

Oceanfront home

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Sea view

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Price per night from

$684

NEW! Luxurious Coastal Condo 5 minutes to Anna Maria Island

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Sea view

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Price per night from

$400

Viewing 38 of 115
rentals in Longboat Key

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