Vacation Rentals & Apartments in Longboat Key

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74 apartments

A Pearl of a Beach Home - now with luxury Saltwater heated pool and hot tub

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Perfect Luxury” Our 5-week stay at this vacation rental was absolutely perfect. The house was everything you could ask for and more. We have stayed in many vacation rentals in the last 20 or so years that we have been coming to anna Maria Island and I have to say this one was right at the top of the list. The kitchen was outfitted with everything you could want. The beds were very comfortable. The neighborhood was nice and quiet. Short walk to the beach. The owners were very nice to deal with and always responded quickly and were very warm and helpful. Definitely can recommend this vacation rental.

Match: Cot available Golf course on site or within 15 min walk

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Price per night from

$474

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Cot available Golf course on site or within 15 min walk

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Price per night from

$149

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White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$628

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$286

Mid Century Home With Private Heated Pool

Tallevast house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$182

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

Bradenton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$280

Stunning & Bright Sarasota Home

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$394

Responds fast! avg. 0 minutes

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$229

Siesta Key Beach : 2 Bedroom, 3 Beds, 3 Bathroom Duplex & Heated Pool

Siesta Key apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$182

#7 Loft Apartment in Historic District Downtown Sarasota

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$304

Anna Maria Island Beach Watch

Bradenton Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$249

AMI Lighthouse Cottage-One Minute Walk To The Beach-Keyless Locks

Cortez cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$164

Anna Maria Island Beach Happy-Direct Beach Front-1BR-1BR

Bradenton Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$231

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$205

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$229

Anna Maria Island Beach Paradise 10

Holmes Beach studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$226

Cozy & Bright+++Minutes to Anna Maria Island, IMG Academy and more

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$117

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$434

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.

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$114

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

Longboat Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$742

Anna Maria Island Beach Haven

Cortez house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$1,495

NEW! Luxurious Coastal Condo 5 minutes to Anna Maria Island

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$400

Anna Maria Island Martinique On The Beach

Holmes Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$776

Beautiful Longboat Key Home!

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 27 minutes

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$514

+++ Clean & Bright +++ Minutes to Anna Maria Island

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$177

Rambo's Beach Retreat! Tradewinds Unit 14

Bradenton Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$451

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$108

Modern Lakerfront Condo! 2x Pools~WiFi~Lanai. By IMG~Beaches~Restaurants~AMI~SRQ

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 11 minutes

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$137

Rare Castle Style Stay! Downtown

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$211

Florida Palms Heaven 2B Villa, near tennis IMG Academy & beaches

South Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$148

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$148

Anna Maria Island Bridge Port Beach Resort

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$172

Anna Maria Island Beach Bay Breeze

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$192

Anna Maria Island Beach View 207

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$185

Anna Maria Island Beach Palace

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$595

Anna Maria Island Beach Palms 2A

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$186

Anna Maria Island Retreat

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$223

Anna Maria Island Beach Palms 8B

Cortez condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Cot available, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$192

Viewing 38 of 74
rentals in Longboat Key

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