Houses Longboat Key

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996 houses

Siesta Key Beach Condo, 2Br/2Ba Direct Beach Front

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“What a great view” We usually rent a house one block from the main Siesta Key beach area. This year friends rented the house and my husband and I stayed in this condo for a week. Loved the view of the beach from the living room! Loved the lani! Location was great. Pool was massive compared to our usual house pool, however we did have to walk thru parking lot to get there. The noise from the hall was annoying. And I did miss my temperpedic mattress, but had a great relaxing time.

Match: Rental types Shared outdoor pool (heated) Microwave

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Price per night from

$328

Bermuda Bay Club Un09 Special discount for February price reduced last minute

Bradenton Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Excellent accomodation and locality” This is the second time we have stayed here, in different units. Everything was excellent. No fuss, and just so convenient with the trolley at the roadside and the beach a walk across the road

Match: Rental types Shared outdoor pool (heated) Microwave

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Price per night from

$344

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

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (heated) Microwave

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Price per night from

$344

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

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Rental types Shared outdoor pool (heated) Microwave

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Price per night from

$287

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

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (heated) Microwave

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Price per night from

$278

Stunning 2,550 Sq.ft House, FL

Bradenton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Shared outdoor pool (heated) Microwave

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Price per night from

$286

Sea Shell Cottage

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Rental types Shared outdoor pool (heated) Microwave

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Price per night from

$172

Off the Hook: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Rental types Shared outdoor pool (heated) Microwave

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Price per night from

$515

Sea Glass Dual Cottages, Sleeps 12, Heated Pool

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Rental types Shared outdoor pool (heated) Microwave

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Price per night from

$402

Tropical Breeze Triple Cottages, Sleeps 16

Sarasota house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 16

Match: Rental types Shared outdoor pool (heated) Microwave

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Price per night from

$683

Flamingo Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (heated) Microwave

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Price per night from

$172

Siesta Dunes #300: By Beachside Management

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (heated) Microwave

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Price per night from

$332

Great location, quiet, peaceful, and comfortable

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Rental types Shared outdoor pool (heated) Microwave

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Price per night from

$46

Coastal Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (heated) Microwave

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Price per night from

$172

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4 minute flip flop walk to the beach! Starfish 2/2

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Microwave, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$339

Amazing Village Cottage! Walk to Whitney Beach!

Longboat Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Microwave, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$394

Private Retreat on Siesta Dr

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 49 minutes

2 of 3 match: Microwave, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$516

St Armand's Private Home on Jackson Drive

Lido Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Microwave, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$382

Limefish

Holmes Beach house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Microwave, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$2,064

"Lido Lookout" Beach Paradise Private Home on Lido Key

Lido Key house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

2 of 3 match: Microwave, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$2,977

Beach Bliss

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

2 of 3 match: Microwave, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$1,145

Relaxing Condo on Siesta Key - Close to beach - Mermaids Rest

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Rental types, Shared outdoor pool (heated), Microwave

2 of 3 filters match

Price per night from

$333

Sea Shell; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 3 match: Rental types, Shared outdoor pool (heated), Microwave

2 of 3 filters match

Price per night from

$320

Crescent Arms; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Shared outdoor pool (heated), Microwave

2 of 3 filters match

Price per night from

$412

Casa Mar - Unit 56: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Shared outdoor pool (heated), Microwave

2 of 3 filters match

Price per night from

$263

Anna Maria Island Runaway Tropical Dream-One Minute Walk To The Beach-Heated Poo

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Rental types, Shared outdoor pool (heated), Microwave

2 of 3 filters match

Price per night from

$216

Longboat Key Cedars Beach House-Pet Friendly-2 Minute To The Beach

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Rental types, Shared outdoor pool (heated), Microwave

2 of 3 filters match

Price per night from

$192

Palm Bay Club - G46: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

2 of 3 match: Rental types, Shared outdoor pool (heated), Microwave

2 of 3 filters match

Price per night from

$286

Siesta Beach House; by Beachside Management

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Shared outdoor pool (heated), Microwave

2 of 3 filters match

Price per night from

$320

Crescent Condos; by Beachside Management

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Shared outdoor pool (heated), Microwave

2 of 3 filters match

Price per night from

$515

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Shared outdoor pool (heated), Microwave

2 of 3 filters match

Price per night from

$272

Shorewalk Condo ED near the Beaches Anna Maria Island, Longboat Key, IMG, Shops

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Shared outdoor pool (heated), Microwave

2 of 3 filters match

Price per night from

$402

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Shared outdoor pool (heated), Microwave

2 of 3 filters match

Price per night from

$344

2 MINUTE WALK TO SIESTA BEACH!! (really) 1 MINUTE TO POOL. GREAT VALUE!!!

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Happy Customer” We had an amazing time. The owners were so nice & made us feel so welcomed. I couldnt have been happier with our stay & we look forward to staying there again soon when life slows back down. Highly recommend this home♡

2 of 3 match: Rental types, Shared outdoor pool (heated), Microwave

2 of 3 filters match

Price per night from

$310

Lifestyle on the island

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Shared outdoor pool (heated), Microwave

2 of 3 filters match

Price per night from

$172

St.Armands Circle condo ( Kingston Arms )

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 25 minutes

2 of 3 match: Rental types, Shared outdoor pool (heated), Microwave

2 of 3 filters match

Price per night from

$258

Luxurious 2 BR Condo-Short Walk to Siesta Beach/1 Small Dog (25 lbs Max) Allowed

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“a fine 2 weeks in Siesta” charming property, that was comfortable for four. The unit was very clean and fresh upon arrival. The neighbours were friendly and the overall property well kept. Siesta Key is a quiet community with usual shopping amenities over the causeway. This property was a brief 10 minute walk to the beach. Would we stay again, yes.

2 of 3 match: Rental types, Shared outdoor pool (heated), Microwave

2 of 3 filters match

Price per night from

$166

GULF FRONT ON #1 Beach! Siesta Dunes (by owner)

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Perfect, Perfect, Perfect” Nice condo with everything close by! Owners were great to deal with and as stated it would be . We plan on visiting again and would recommend this place to anyone.

2 of 3 match: Rental types, Shared outdoor pool (heated), Microwave

2 of 3 filters match

Price per night from

$272

Viewing 38 of 996
rentals in Longboat Key

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