Houses Longboat Key

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526 houses

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) Walking trips

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Price per night from

$344

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Steps to beach and bay on beautiful Anna Maria Island

Bradenton Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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

2 of 3 filters match

Price per night from

$101

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, Walking trips, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$192

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, Walking trips, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$217

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, Walking trips, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$165

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

2 of 3 filters match

Price per night from

$430

“Clean comfortable Siesta Key Condo with all the comforts of home...Perfect!” The condo is walking distance to shops, restaurants and quaint local tiki bar! The beach is a short walk across the street and through the beach-front section of the complex with lounge chairs and umbrellas available, very nice! I didn't mention the 2 pools (one beachside) and nice gym facilities also just downstairs of the unit. The covered parking space was an added plus! The condo was clean and very comfortable with all of the amenities of home which is greatly appreciated! You can even enjoy the view of the bayside inlet and beautiful landscaping from the kitchen through the entire wall of glass doors in the living/dining room! We had a wonderful week! The property owner Vic supplied more than enough information on the condo, local businesses and area maps! He was such a pleasure to work with! Thanks again Vic! We are already planning our next trip to Siesta Key in May!!

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

2 of 3 filters match

Price per night from

$144

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

2 of 3 filters match

Price per night from

$144

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

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

2 of 3 filters match

Price per night from

$338

Siesta Key private beach access

Siesta Key villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Siesta Key Townhouse” This was a wonderful place to stay! The house was very clean and spacious and had everything we needed for a week at the beach.

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

2 of 3 filters match

Price per night from

$509

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, Walking trips, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$271

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

2 of 3 filters match

Price per night from

$107

Charming Siesta Key Village Unbeatable Location

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

2 of 3 filters match

Price per night from

$189

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

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

2 of 3 filters match

Price per night from

$161

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

2 of 3 filters match

Price per night from

$284

3BR/4BA TOWNHOUSE - POOL VIEW PARADISE - PRIVATE BEACH ACCESS

Siesta Key townhouse

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 38 minutes

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

2 of 3 filters match

Price per night from

$430

Responds fast! avg. 11 minutes

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

2 of 3 filters match

Price per night from

$132

"Lido Lookout" Beach Paradise Private Home on Lido Key

Lido Key house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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

2 of 3 filters match

Price per night from

$2,977

Amazing Village Cottage! Walk to Whitney Beach!

Longboat Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

2 of 3 filters match

Price per night from

$393

Private Retreat on Siesta Dr

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 49 minutes

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

2 of 3 filters match

Price per night from

$2,061

Beach Bliss

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

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

2 of 3 filters match

Price per night from

$1,145

Great location, quiet, peaceful, and comfortable

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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

2 of 3 filters match

Price per night from

$46

Anna Maria Island Beach Watch

Bradenton Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

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

2 of 3 filters match

Price per night from

$248

Anna Maria Island Beach Happy-Direct Beach Front-1BR-1BR

Bradenton Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 20 minutes

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

2 of 3 filters match

Price per night from

$228

Anna Maria Island Beach Haven

Cortez house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

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

2 of 3 filters match

Price per night from

$1,500

Anna Maria Island Beach Palace

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

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

2 of 3 filters match

Price per night from

$592

AMI Gulf Lookout-Views Of The Gulf From Every Room-Rooftop Terrace

Cortez house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

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

2 of 3 filters match

Price per night from

$385

Anna Maria Beach Serenity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

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

2 of 3 filters match

Price per night from

$950

Anna Maria Island Edgewater Bungalow

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

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

2 of 3 filters match

Price per night from

$298

Anna Maria Island Sun's Up A

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

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

2 of 3 filters match

Price per night from

$493

Anna Maria Island Sun's Up B

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

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

2 of 3 filters match

Price per night from

$480

Anna Maria Island Surfside Bungalow

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

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

2 of 3 filters match

Price per night from

$355

2 bedroom Condo Bay Oaks Siesta Key

Sarasota condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

1 of 3 match: Rental types, Walking trips, Shared outdoor pool (heated)

1 of 3 filters match

Price per night from

$573

Direct Beachfront 2 BR Condo on Florida’S Beautiful Gulf Coast!

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Rental types, Walking trips, Shared outdoor pool (heated)

1 of 3 filters match

Price per night from

$430

Stunning 2,550 Sq.ft House, FL

Bradenton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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

2 of 3 filters match

Price per night from

$286

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.

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

2 of 3 filters match

Price per night from

$328

Viewing 38 of 526
rentals in Longboat Key

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