Vacation Rentals & Apartments in Longboat Key

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Siesta Key Beach Cottages on Crescent

Siesta Key cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Children's pool Pets allowed

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Price per night from

$224

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Anna Maria Islands best location Heated pool Best prices!

Anna Maria Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Children's pool

1 of 2 filters match

Price per night from

$861

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.

1 of 2 match: Pets allowed, Children's pool

1 of 2 filters match

Price per night from

$477

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Pets allowed, Children's pool

1 of 2 filters match

Price per night from

$206

Seaplace Condo - 1975 GMD 104

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Pets allowed, Children's pool

1 of 2 filters match

Price per night from

$192

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

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 56 minutes

1 of 2 match: Pets allowed, Children's pool

1 of 2 filters match

Price per night from

$114

Downtown Sarasota Historic Burns Court Adorable Bungalow

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$295

One Bedroom in Historic Burns Square District downtown

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$316

#7 Loft Apartment in Historic District Downtown Sarasota

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$306

Secure, Cozy & Cute Private Sleeping Studio for 2

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$235

Charming Private Studio in Historic Downtown Area

Sarasota studio

  • Studio
  • 1 bathroom
  • sleeps 3

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$259

Jacaranda Artist Retreat

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$218

BAY FRONT HOUSE WITH PRIVATE DOCK

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 31 minutes

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$345

Light and Airy and Private, Great Location

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$230

Sarasota Downtown, Best Location For Your Vacation !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Responds fast! avg. 1 hour 46 minutes

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$194

Tiny House Siesta - Yellow Lifeguard Stand Tiny House

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$423

Tiny House Siesta - Red Lifeguard Stand

Siesta Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$443

Tiny House Siesta - Tiny Aqua Oasis- Tiny House that sleeps 6 comfortably

Siesta Key hotel apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$445

Tiny House Siesta - Sand Dollar – A private master loft and open living space

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$448

Gorgeous Waterfront Apartment Steps From 100Ft Fishing Dock And Tiki.

Palmetto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$167

Luxury Modern Oasis in Heart of Sarasota

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$1,032

Beautiful Longboat Key Home!

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 27 minutes

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$517

Remodeled Exquisite Home. 10 min from the Beaches of Anna Maria Island. 7min IMG

South Bradenton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$344

The Hideaway: 4/2 W Heated Pool and Outdoor Spaces, 10 mins to Sarasota Beach

Gulf Gate Estates house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$373

Blue Heron Inn: 1/1 Spacious Apartment, 15 mins to beaches, pet friendly

Oneco apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$127

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$167

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$144

Lazy Manatee Apt: 15 mins to beach and SRQ airport - pet friendly!

Oneco apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$144

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$108

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$295

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$183

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$316

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$138

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$173

Tripletail

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$1,722

Lady Palm Apt: 1/1 with 2 beds, garden vibes and outdoor spaces! Pet friendly

Bradenton apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$144

Downtown Apartment in Historic Burns Square downtown Sarasota

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$282

Delightful Oasis #2

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$178

Viewing 38 of 185
rentals in Longboat Key

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