Houses Longboat Key

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528 houses

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) Car not required

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Price per night from

$229

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) Car not required

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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) Car not required

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Price per night from

$288

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) Car not required

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Price per night from

$279

Sea Shell Cottage

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Rental types Shared outdoor pool (heated) Car not required

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Price per night from

$173

Off the Hook: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Rental types Shared outdoor pool (heated) Car not required

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Price per night from

$515

Limefish

Holmes Beach house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Rental types Shared outdoor pool (heated) Car not required

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Price per night from

$2,061

Sea Glass Dual Cottages, Sleeps 12, Heated Pool

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Rental types Shared outdoor pool (heated) Car not required

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Price per night from

$403

Tropical Breeze Triple Cottages, Sleeps 16

Sarasota house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 16

Match: Rental types Shared outdoor pool (heated) Car not required

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Price per night from

$684

Flamingo Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (heated) Car not required

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Price per night from

$173

Siesta Dunes #300: By Beachside Management

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (heated) Car not required

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Price per night from

$331

Coastal Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (heated) Car not required

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Price per night from

$173

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Ten35 Seaside - Direct Gulf View: Residence 601

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Shared outdoor pool (heated), Car not required

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Price per night from

$927

Crystal Sands Unit 308 Siesta Key, Florida

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Vacation Rental” We have been coming to Siesta Key for our Vacations for years... We have stayed at a number of Units at Crystal Sands, Crescent arms and El Presidente... Crystal Sands Unit 308 is one of the best Units we have stayed at... It has a great view of the Beach and Pool... You can watch the Sunsets and Moonsets right from the Lanai... The Unit is Roomy, Clean and had all the appliances, Dishes and Linens we needed... The Washer\Dryer in the Unit is very convenient... It has a New 60" Hdtv in the Living Room with an incredible picture... Jim left printed instructions for the Hdtv, Washer and Dryer which made it very easy to use the appliances in the Unit... We are looking forward to staying in Crystal Sands Unit 308 again for our next trip to Siesta Key...

2 of 3 match: Rental types, Shared outdoor pool (heated), Car not required

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Price per night from

$432

Jamaica Royal Villas - Villa 42; by Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Rental types, Shared outdoor pool (heated), Car not required

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Price per night from

$240

Anna Maria Island Vacation Rental

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Island Paradise” The moment we arrived, exhausted after many delays and problems, the Thomas' home became our home. The condo is well appointed, with comfortable beds, a wonderful kitchen and a fully stocked linen closet, right down to beach towels. Laine, Kevin and Howard are so responsive and saw to all of our needs. Location was prime. We walked to get groceries, eat and do other shopping. There were 7 miles of beaches to explore and the quaint villages of anna Maria and Cortez and Bridge Street kept us occupied when we weren't soaking up the sun. The lanai was my favorite place to drink my coffee and check out the action at the pool each morning . We ate the majority of our meals there, under the twinkling lights. It was a wonderful month!

2 of 3 match: Rental types, Shared outdoor pool (heated), Car not required

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Price per night from

$166

Crescent Arms; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Shared outdoor pool (heated), Car not required

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Price per night from

$411

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), Car not required

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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), Car not required

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Price per night from

$515

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), Car not required

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Price per night from

$263

Sea Shell; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 3 match: Rental types, Shared outdoor pool (heated), Car not required

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Price per night from

$320

120 Steps to the Beach with beach gear included!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Shared outdoor pool (heated), Car not required

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Price per night from

$424

Family Tides - High Tides: By Beachside Management

Siesta Key apartment

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

2 of 3 match: Rental types, Shared outdoor pool (heated), Car not required

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Price per night from

$549

“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, Shared outdoor pool (heated), Car not required

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Price per night from

$144

2 of 3 match: Rental types, Shared outdoor pool (heated), Car not required

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Price per night from

$334

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), Car not required

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Price per night from

$259

Cathy's Crescent Condos-Siesta Key, FL GULF FRONT

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great View” We stayed at Kathy’s condo during the 4th of July week. The Condo was great and the view was amazing. We enjoyed the fireworks display and easy access to the beach. We look forward to renting her condo again in the future.

2 of 3 match: Rental types, Shared outdoor pool (heated), Car not required

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Price per night from

$316

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, Shared outdoor pool (heated), Car not required

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Price per night from

$102

Charming Siesta Key Village Unbeatable Location

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Shared outdoor pool (heated), Car not required

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Price per night from

$190

GULF COAST DESTINATION

Bradenton Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Shared outdoor pool (heated), Car not required

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Price per night from

$201

Sol y Mar - Casita Mar: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Shared outdoor pool (heated), Car not required

2 of 3 filters match

Price per night from

$240

Living the Dream - Pink Flamingo: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Rental types, Shared outdoor pool (heated), Car not required

2 of 3 filters match

Price per night from

$320

Beach Walk: By Beachside Management

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Shared outdoor pool (heated), Car not required

2 of 3 filters match

Price per night from

$515

Bianco Sands 2 Bedroom - 2 Bath; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Shared outdoor pool (heated), Car not required

2 of 3 filters match

Price per night from

$297

Bianco Sands - 3 Bedroom 2 Bath: By Beachside Management

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Shared outdoor pool (heated), Car not required

2 of 3 filters match

Price per night from

$308

Crescent Beach Villas - La Perlita: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Shared outdoor pool (heated), Car not required

2 of 3 filters match

Price per night from

$274

Casa Mar - Unit 20: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Shared outdoor pool (heated), Car not required

2 of 3 filters match

Price per night from

$308

Casa Mar - Unit 58: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 2

2 of 3 match: Rental types, Shared outdoor pool (heated), Car not required

2 of 3 filters match

Price per night from

$308

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rentals in Longboat Key

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