Houses Longboat Key

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396 houses

Anna Maria Island/ IMG Academy/ Beach/ HotTub/ Bikes/ Kayaks/ Golf/ Fishing

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Trampoline Wheelchair accessible

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Price per night from

$287

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TROPICCAL, 4 min from the beaches! Meticulously cleaned and sanitized!

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

“Lovely home in an awesome location!” Literally a minute's drive from the beach, this very clean and welcoming home is also convenient to great restaurants and shopping opportunities. It really is in a perfect location, especially considering the affordable price. Walking to restaurants and a rental shop is easy thanks to the sidewalk on Cortes. We even enjoyed a morning run to the beach - biking to the beach would also be a great option (3.5 mi one way.) The home might appear small at first, but we fit 6 comfortably, including 4 teenagers! The best part is the lovely décor that greets you after a long day at the beach or running around. Two thumbs up!

Responds fast! avg. 2 hours 33 minutes

2 of 3 match: Trampoline, Rental types, Wheelchair accessible

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Price per night from

$144

White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Trampoline, Rental types, Wheelchair accessible

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Price per night from

$633

Outdoor Oasis Awaits! Your perfect vacation spot just steps away from the beach

Anna Maria Island house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

2 of 3 match: Trampoline, Rental types, Wheelchair accessible

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Price per night from

$1,024

2 of 3 match: Trampoline, Rental types, Wheelchair accessible

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Price per night from

$794

Modern home with Private pool, walk to the beach, Putting green & Ping pong

Anna Maria house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

2 of 3 match: Trampoline, Rental types, Wheelchair accessible

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Price per night from

$914

2 of 3 match: Trampoline, Rental types, Wheelchair accessible

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Price per night from

$1,035

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

2 of 3 match: Trampoline, Rental types, Wheelchair accessible

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Price per night from

$1,003

A Siesta Tropical Retreat - Island Pool Oasis in Village & 2 blocks to Beach

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

“Your best choice for location!” We stayed for 10 lovely days in this home and I have to say It was an even better location than I expected. Everything you could want to do is in walking distance or you can walk to the village (maybe a 3 minute walk)and hop in a free taxi . The house is well appointed and beds are very comfortable. We traveled with a 10 yr.old, 11yr. old , and 15 yr. old my 15 yr. old niece slept in the trundle bed and commented on how comfortable the bed was. In the kitchen you will find a drawer full of menus for the many nearby restaurants and information for water activities. I highly recommend parasailing while your there ! Considering how close everything is the street is very quiet and the owners were great to deal with. Thanks Kathi and Grant!

2 of 3 match: Trampoline, Rental types, Wheelchair accessible

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Price per night from

$502

Indulge in a spacious 4-bedroom rental with private pool and beach access!

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

2 of 3 match: Trampoline, Rental types, Wheelchair accessible

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Price per night from

$978

Discover the perfect beachfront getaway with a private pool & hot tub.

Siesta Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Trampoline, Rental types, Wheelchair accessible

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Price per night from

$857

Experience the luxury of private beach living with TWO heated pools!

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Trampoline, Rental types, Wheelchair accessible

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Price per night from

$1,156

The Corner Retreat

Bradenton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Trampoline, Rental types, Wheelchair accessible

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Price per night from

$183

Cloud 9

Anna Maria house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 8

2 of 3 match: Trampoline, Rental types, Wheelchair accessible

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Price per night from

$1,947

2 of 3 match: Trampoline, Rental types, Wheelchair accessible

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Price per night from

$457

Aqua Pina: 2 kings, bar area, foosball, sleep 14

Bradenton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

2 of 3 match: Trampoline, Rental types, Wheelchair accessible

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Price per night from

$1,098

Coquina Sands, view beach from balcony, priv pool

Holmes Beach house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Trampoline, Rental types, Wheelchair accessible

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Price per night from

$458

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

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Trampoline, Rental types, Wheelchair accessible

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Price per night from

$279

Little Palms Villa. A lakeside home with style.

Bradenton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Excellent” Our stay at 4638 Runabout way was amazing. We loved that the house was very nice, spacious, and clean for my family and I. We loved swimming in the pool everyday. The service was excellent all around. We would definitely stay there again.

1 of 3 match: Rental types, Trampoline, Wheelchair accessible

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Price per night from

$196

St.Armands Circle condo ( Kingston Arms )

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 25 minutes

1 of 3 match: Rental types, Trampoline, Wheelchair accessible

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Price per night from

$259

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♡

1 of 3 match: Rental types, Trampoline, Wheelchair accessible

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Price per night from

$311

House of Blues - Lovely 2-Bedroom Condo with Pool, W&D and Patio

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Trampoline, Wheelchair accessible

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Price per night from

$201

Come join us for your Winter Migration!!!!!!!!!!

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Rental types, Trampoline, Wheelchair accessible

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Price per night from

$103

Unit #112 Sand Cay Beach Resort Pool and Garden View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Trampoline, Wheelchair accessible

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Price per night from

$278

2-Unit Beach to Bay Cottage...NOT Grandma's place!...100 feet to beach!

Bradenton Beach cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Best home away from home at the beach.” I spent a lot of time searching for a bungalow at the beach and my expectations were surpassed when I opened the door! The owners were thoughtful in design, layout and furnishings to provide a laid back experience at the beach. I wished I could have stayed forever - it was that nice. I especially enjoyed the fully stocked kitchen which included colorful dishes to match the colorful walls and great blue floor! Best of all - location - you can walk everywhere as you are right in the historic Bridge Street neighborhood.

1 of 3 match: Rental types, Trampoline, Wheelchair accessible

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Price per night from

$246

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Trampoline, Wheelchair accessible

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Price per night from

$345

Anna Maria The Pink Flamingo

Holmes Beach cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 41 minutes

1 of 3 match: Rental types, Trampoline, Wheelchair accessible

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Price per night from

$460

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.

1 of 3 match: Rental types, Trampoline, Wheelchair accessible

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Price per night from

$273

“Anniversary Trip” Had a wonderful time at LA Siesta Condominiums for our anniversary vacation. Beautifully furnished and do close to the best beach in the USA

1 of 3 match: Rental types, Trampoline, Wheelchair accessible

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Price per night from

$246

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, Trampoline, Wheelchair accessible

1 of 3 filters match

Price per night from

$432

Zilli Tower 503

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 3 match: Rental types, Trampoline, Wheelchair accessible

1 of 3 filters match

Price per night from

$344

Zilli Ocean Front 202 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 3 match: Rental types, Trampoline, Wheelchair accessible

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Price per night from

$310

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Trampoline, Wheelchair accessible

1 of 3 filters match

Price per night from

$273

1 of 3 match: Rental types, Trampoline, Wheelchair accessible

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Price per night from

$284

180 Panoramic beach View and amazing Sunset.

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 3 match: Rental types, Trampoline, Wheelchair accessible

1 of 3 filters match

Price per night from

$457

Zilli Ocean Front 201 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 3 match: Rental types, Trampoline, Wheelchair accessible

1 of 3 filters match

Price per night from

$297

Excellent Location - Gulf/Beach View - Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 38 minutes

1 of 3 match: Rental types, Trampoline, Wheelchair accessible

1 of 3 filters match

Price per night from

$344

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

1 of 3 match: Rental types, Trampoline, Wheelchair accessible

1 of 3 filters match

Price per night from

$117

Viewing 38 of 396
rentals in Longboat Key

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