Houses Longboat Key

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799 houses

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Rental types Kettle Safe Staffed property

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Price per night from

$149

The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Rental types Kettle Safe Staffed property

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Price per night from

$343

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Spacious Apt. #1 Historic Walkable Downtown, between Siesta & Lido Beach

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Rental types, Kettle, Safe, Staffed property

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Price per night from

$482

Secure, Cozy & Cute Private Sleeping Studio for 2

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

3 of 4 match: Rental types, Kettle, Safe, Staffed property

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Price per night from

$234

Jamaica Royale #104! Completely renovated, Gulf side, beautiful 2b/2b Condo!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Rental types, Kettle, Safe, Staffed property

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Price per night from

$336

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

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

3 of 4 match: Rental types, Kettle, Safe, Staffed property

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Price per night from

$177

Zilli Tower 503

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

3 of 4 match: Rental types, Kettle, Safe, Staffed property

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Price per night from

$343

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Rental types, Kettle, Safe, Staffed property

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Price per night from

$430

Lido Beach Villa, 1.2k sf, 1 block to the beach

Lido Key villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Rental types, Kettle, Safe, Staffed property

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Price per night from

$184

Luxury Resort Sleeps 26!

Palma Sola house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 26

Responds fast! avg. 3 hours 39 minutes

3 of 4 match: Kettle, Rental types, Safe, Staffed property

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Price per night from

$2,289

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.

3 of 4 match: Rental types, Kettle, Safe, Staffed property

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Price per night from

$512

Siesta Key Townhouse across from Pristine Sands of Siesta Key 2B/2B sleeps 6

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Fantastic week in Siesta Key” The townhouse was fantastic and fully equipped with everything we needed for a very comfortable week. The location was outstanding - right across from the beach and the free trolley to the Village stopped right outside. The garage had everything the family needed to take to the beach and we met some lovely people around the pool. Thank you Michelle for your hospitality - we hope to be back soon.

3 of 4 match: Rental types, Kettle, Safe, Staffed property

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Price per night from

$189

Florida Ocean Front Condo

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Rental types, Kettle, Safe, Staffed property

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Price per night from

$620

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.

3 of 4 match: Rental types, Kettle, Safe, Staffed property

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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

3 of 4 match: Rental types, Kettle, Safe, Staffed property

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Price per night from

$742

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

3 of 4 match: Rental types, Kettle, Safe, Staffed property

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Price per night from

$117

🏝Paradise on the Sarasota Bay, Close to Gulf Beaches🏝 (Sarasota)

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 4 match: Rental types, Kettle, Safe, Staffed property

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Price per night from

$193

Amazing views, 11th flr, On the beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 4 match: Rental types, Kettle, Safe, Staffed property

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Price per night from

$408

Sarasota Downtown, Best Location For Your Vacation !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Responds fast! avg. 1 hour 57 minutes

2 of 4 match: Rental types, Safe, Kettle, Staffed property

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Price per night from

$193

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Kettle, Safe, Staffed property

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Price per night from

$270

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Kettle, Safe, Staffed property

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Price per night from

$434

Crescent Beach Villas - La Estrella: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Kettle, Safe, Staffed property

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Price per night from

$274

Private Beach Access - Home away from Home - 2 BR 2 BA - Furnished Condo

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Kettle, Safe, Staffed property

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Price per night from

$178

3 of 4 match: Staffed property, Rental types, Kettle, Safe

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Price per night from

$182

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Rental types, Safe, Kettle, Staffed property

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Price per night from

$229

ISLAND TOWNHOUSE - 200 Steps to the BEACH

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 43 minutes

3 of 4 match: Staffed property, Rental types, Kettle, Safe

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Price per night from

$206

Luxury Modern Oasis in Heart of Sarasota

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 4 match: Staffed property, Rental types, Kettle, Safe

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Price per night from

$1,026

White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Rental types, Kettle, Safe

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Price per night from

$628

Coastal Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Staffed property, Rental types, Kettle, Safe

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Price per night from

$172

Flamingo Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Staffed property, Rental types, Kettle, Safe

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Price per night from

$172

Sea Shell Cottage

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Staffed property, Rental types, Kettle, Safe

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Price per night from

$172

The Corner Retreat

Bradenton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

3 of 4 match: Staffed property, Rental types, Kettle, Safe

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Price per night from

$182

Cloud 9

Anna Maria house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Rental types, Kettle, Safe

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Price per night from

$1,947

3 of 4 match: Staffed property, Rental types, Kettle, Safe

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Price per night from

$344

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

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Staffed property, Rental types, Kettle, Safe

3 of 4 filters match

Price per night from

$277

2 of 4 match: Rental types, Safe, Kettle, Staffed property

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Price per night from

$143

2 of 4 match: Rental types, Safe, Kettle, Staffed property

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Price per night from

$283

Zilli Ocean Front 201 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

2 of 4 match: Rental types, Safe, Kettle, Staffed property

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Price per night from

$296

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rentals in Longboat Key

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