Houses Longboat Key

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991 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) Fridge

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Price per night from

$329

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) Fridge

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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) Fridge

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Price per night from

$345

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) Fridge

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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) Fridge

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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) Fridge

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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) Fridge

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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) Fridge

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Price per night from

$516

Sea Glass Dual Cottages, Sleeps 12, Heated Pool

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Rental types Shared outdoor pool (heated) Fridge

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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) Fridge

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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) Fridge

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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) Fridge

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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) Fridge

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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) Fridge

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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: Fridge, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$339

"Lido Lookout" Beach Paradise Private Home on Lido Key

Lido Key house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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

2 of 3 filters match

Price per night from

$2,983

Amazing Village Cottage! Walk to Whitney Beach!

Longboat Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

2 of 3 filters match

Price per night from

$517

St Armand's Private Home on Jackson Drive

Lido Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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

2 of 3 filters match

Price per night from

$2,066

Beach Bliss

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

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

2 of 3 filters match

Price per night from

$1,148

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), Fridge

2 of 3 filters match

Price per night from

$333

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), Fridge

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), Fridge

2 of 3 filters match

Price per night from

$218

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), Fridge

2 of 3 filters match

Price per night from

$191

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), Fridge

2 of 3 filters match

Price per night from

$286

Crescent Arms; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

2 of 3 filters match

Price per night from

$411

Crescent Condos; by Beachside Management

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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

2 of 3 filters match

Price per night from

$515

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), Fridge

2 of 3 filters match

Price per night from

$320

Sea Shell; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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

2 of 3 filters match

Price per night from

$320

Runaway Bay - Bradenton Beach - Bay View Unit 193

Anna Maria Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Home away from home” This place is an incredible value. It's spacious and comfortable, and we felt right at home. Sarasota Bay is just steps from the back patio, and it's so lovely to sit outside and watch water--so many fish, dolphins, and birds right there. Everything was in good working order and clean upon our arrival. The beach is a quick walk across the street from the complex, and we spent a lot of time at the heated pool. We would love to rent this unit again! PERFECT LOCATION.

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

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Price per night from

$209

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), Fridge

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), Fridge

2 of 3 filters match

Price per night from

$402

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

2 of 3 filters match

Price per night from

$431

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

2 of 3 filters match

Price per night from

$285

Ideal Retreat next to USA's #1 Beach—Siesta Key

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

2 of 3 filters match

Price per night from

$161

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), Fridge

2 of 3 filters match

Price per night from

$345

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), Fridge

2 of 3 filters match

Price per night from

$259

Viewing 38 of 991
rentals in Longboat Key

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