Houses Longboat Key

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377 houses

Anna Maria Island/ IMG Academy/ Beach/ HotTub/ Bikes/ Kayaks/ Golf/ Fishing

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Safe Swing set or jungle gym

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Price per night from

$286

White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Safe Swing set or jungle gym

All filters match

Price per night from

$630

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

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

2 of 3 match: Rental types, Safe, Swing set or jungle gym

2 of 3 filters match

Price per night from

$177

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

2 of 3 match: Rental types, Safe, Swing set or jungle gym

2 of 3 filters match

Price per night from

$117

Florida Ocean Front Condo

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Safe, Swing set or jungle gym

2 of 3 filters match

Price per night from

$622

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.

2 of 3 match: Rental types, Safe, Swing set or jungle gym

2 of 3 filters match

Price per night from

$115

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

Longboat Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Safe, Swing set or jungle gym

2 of 3 filters match

Price per night from

$745

TROPICCAL, 4 min from the beaches! Meticulously cleaned and sanitized!

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

“Lovely home in an awesome location!” Literally a minute's drive from the beach, this very clean and welcoming home is also convenient to great restaurants and shopping opportunities. It really is in a perfect location, especially considering the affordable price. Walking to restaurants and a rental shop is easy thanks to the sidewalk on Cortes. We even enjoyed a morning run to the beach - biking to the beach would also be a great option (3.5 mi one way.) The home might appear small at first, but we fit 6 comfortably, including 4 teenagers! The best part is the lovely décor that greets you after a long day at the beach or running around. Two thumbs up!

Responds fast! avg. 2 hours 33 minutes

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$144

#1 EXCLUSIVE Siesta Key Beach House /3 payments

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$258

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$182

Siesta Key Waterfront Estate heated Pool Privacy!

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$716

Stunning & Serene +++ Minutes from Anna Maria Island, IMG Academy and more!

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

1 of 3 match: Rental types, Safe, Swing set or jungle gym

1 of 3 filters match

Price per night from

$114

Luxury Modern Oasis in Heart of Sarasota

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$1,029

Beautiful Longboat Key Home!

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 27 minutes

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$515

SUNSET VISTA ON LONGBOAT KEY

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Rental types, Swing set or jungle gym, Safe

1 of 3 filters match

Price per night from

$286

Coastal Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$172

Flamingo Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$172

Sea Shell Cottage

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$172

Dream beach, pool/spa retreat!

Siesta Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$344

The Corner Retreat

Bradenton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$182

Luxury Resort Sleeps 26!

Palma Sola house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 26

Responds fast! avg. 3 hours 39 minutes

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$2,284

Cloud 9

Anna Maria house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 8

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$1,943

Buena Vida: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$513

ISLAND TOWNHOUSE - 200 Steps to the BEACH

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 43 minutes

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$206

****Walk to Beach-5min! Waterfront Canal! Private Pool~spa~Kayaks, Bikes!

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$454

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

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$277

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$344

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$602

The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$344

Responds fast! avg. 11 minutes

1 of 3 match: Rental types, Safe, Swing set or jungle gym

1 of 3 filters match

Price per night from

$132

Seaplace Condo - 1975 GMD 104

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Rental types, Safe, Swing set or jungle gym

1 of 3 filters match

Price per night from

$192

2 Bedroom, 2 Bathroom condo / Heated pool / 7 minute walk to beach

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Safe, Swing set or jungle gym

1 of 3 filters match

Price per night from

$178

Tropical Breeze Triple Cottages, Sleeps 16

Sarasota house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 16

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$681

Sea Glass Dual Cottages, Sleeps 12, Heated Pool

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$401

Newly renovated beach house near AMI free trolley stop with Private pool

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$561

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.

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$630

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

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$121

Great Townhouse Very Close to the Beach, Shops, and Restaurants

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Swing set or jungle gym, Rental types, Safe

2 of 3 filters match

Price per night from

$344

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rentals in Longboat Key

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