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Dog Friendly Vacation Rentals in Longboat Key - FlipKey

491 pet friendly apartments in Longboat Key

Longboat Key Condo w/ Pool Access- Walk to Bay!

Longboat Key apartment

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$229

Charming Beach House in Longboat Key/ pool/pet/dock

Longboat Key house

  • Beach / lakeside relaxation
  • •  Nearest beach 0.02 mi
  • •  Swimming pool
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$263

Longboat Key Retreat

Longboat Key house

  • Beach / lakeside relaxation
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$148

55+ Community with pool and club house

Longboat Key villa

  • Child Friendly
  • •  Air conditioning
  • •  Pet Friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$81

Private Bungalow on Canal a block from Beach

Longboat Key house

  • Child Friendly
  • •  Air conditioning
  • •  Pet Friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$201

BBB on Marbury lane-Beach, boating, BBQ!

Longboat Key house

  • Child Friendly
  • •  Pet Friendly
  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$287

Lovely Tropical Longboat Town house

Longboat Key townhouse

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$147

Beautiful Island Sanctuary Best Location in South Longboat Key!

Longboat Key house

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$487

Longboat Key Condo w/Lanai, Walk to Beach & Shops

Longboat Key condo

  • Child Friendly
  • •  Air conditioning
  • •  Pet Friendly
  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$103

Fabulous Longboat Key - A Mermaids' Oasis 4 minute walk to beach!

Longboat Key house

  • Child Friendly
  • •  Air conditioning
  • •  Pet Friendly
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$172

Longboat Key Cedars Resort

Longboat Key condo

  • Swimming pool
  • •  Ask about children
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$126

Pet Friendly on Longboat Key

Longboat Key apartment

  • Beach / lakeside relaxation
  • •  Child Friendly
  • •  Car not necessary
  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“What a Find!!!” This is a one of the best locations on Longboat. We visit Longboat every year to see my father. We were able to find this condo out from just a simple google search. The condo was very clean. We loved the decorations and the full kitchen. We will return!!!

Price per night from

$138

EXTREME POLYNESIAN BEACH HOUSE with BOAT/ KAYAKS

Longboat Key house

  • Beach / lakeside relaxation
  • •  Child Friendly
  • •  Car not necessary
  • 6 bedrooms
  • 6 bathrooms
  • sleeps 20

Price per night from

$803

Castle in the Sky Near Beach and Tennis

Longboat Key house

  • Beach / lakeside relaxation
  • •  Nearest beach 2 mi
  • •  Child Friendly
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

“Great Family Holiday Vacation” Our two families of 8 people total enjoyed our stay at Castle in the sky very much. The house is large but very comfortable. The weather in January can be fickle so one day the air conditioner is on, the next day the heater was on but the house is overall bright and cheerful and the décor is very pleasant. We ate in about half the time and walked to some nearby restaurants which were convenient. The kitchen has plenty of room and is well stocked with silverware and cookware. The resort pool is heated and there is a nature park nearby which we used for a jogging trail which was great. The water was too cold for the beach but there is a lot of beach chairs and items to use in the garage if you need them This was the largest home we found on Flipkey that could accommodate our group and wouldn't break the bank. We weren't directly on the water but there's so much to do nearby that it didn't really matter to us. We would stay again and likely will next winter. The owner was forthright with everything and pleasant to work with.

Price per night from

$228

Great rentals within 20 miles that match your search

AnnaMariaIsland a Paradise. MINUMIM RENTAL 2 WEEKS

Bradenton Beach apartment

  • Beach / lakeside relaxation
  • •  Swimming pool
  • •  Child Friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$173

On the Beach Paradise u

Holmes Beach cottage

  • Beach / lakeside relaxation
  • •  Child Friendly
  • •  Car not necessary
  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$207

Casa Paradiso - Come Stay in Paradise - Sit, Relax and Enjoy Siesta Key

Siesta Key house

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

Price per night from

$135

Downtown Sarasota #12

Sarasota condo

  • Air conditioning
  • •  Pet Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$78

Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa

Siesta Key house

  • Swimming pool
  • •  Child Friendly
  • •  Car not necessary
  • 5 bedrooms
  • 4 bathrooms
  • sleeps 13

Price per night from

$568

Beach House on Anna Maria Island-Rental Openings

Holmes Beach villa

  • Beach / lakeside relaxation
  • •  Swimming pool
  • •  Child Friendly
  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$230

Siesta Key Beach Cottages on Crescent

Siesta Key cottage

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$226

Heated Pool 2 Bed 3 Bath near Siesta Key

Sarasota house

  • Nearest beach 3 mi
  • •  Swimming pool
  • •  Child Friendly
  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

“Florida Trip” We rented this lovely home through Flipkey. This was a great rental for two couples and had everything you could possibly want at your fingertips. Just like home. Location was great and is located in a nice quiet neighborhood. Monica, the owner was even nice enough to leave golf clubs at the house for our husbands. Pool was lovely and area very spacious and private. Would definitely recommend!

Price per night from

$167

Unique Siesta Key Pool Home

Siesta Key house

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$195

Pool home, mins to Anna Maria Is & IMG Academy

Bradenton house

  • Child Friendly
  • •  Pet Friendly
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$287

Casita Blanca- 2BR, Private Beach Access, Communal Heated Pool [Sleeps 4]

Sarasota house

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$301

Upscale, Coach Home, Country Club Property

Bradenton condo

  • Child Friendly
  • •  Air conditioning
  • •  Pet Friendly
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$172

One Bedroom Cottage on Vista Del Lago MH & RV Resort, 55+ Community

Oneco cottage

  • Air conditioning
  • •  Pet Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$68

Fr $490/wk 2BR/2BA condo nr. Siesta Key WIFI, gym, pool, king bed

Sarasota condo

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$109

Buena Vista on Anna Maria Island

Holmes Beach house

  • Child Friendly
  • •  Air conditioning
  • •  Pet Friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$373

Three bedroom house directly on beach with gulf vi

Siesta Key house

  • Beach / lakeside relaxation
  • •  Child Friendly
  • •  Air conditioning
  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

Price per night from

$344

2 bedroom/1 bath Contemporary Beach Cottage

Siesta Key house

  • Child Friendly
  • •  Air conditioning
  • •  Pet Friendly
  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$195

Elegant 4 Bedroom 3 bath Executive Home - HEATED POOL near Siesta Key Beaches!!!

Sarasota house

  • Nearest beach 4 mi
  • •  Swimming pool
  • •  Child Friendly
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

“Wonderful property!” Thoroughly enjoyed our stay in this lovely home. It was clean, spacious, and relaxing. From the heated pool to the gorgeous lanai, it was wonderful. The kitchen was well-equipped and we were able to enjoy Thanksgiving dinner with 15 family and friends in a very comfortable setting. The 4 bedrooms are clean and spacious. Lots of attention to detail. About 10 minutes to Siesta Key beach. Would highly recommend.

Price per night from

$281

Spacious 2 Bedroom with Water View, 55+ Community

Ellenton house

  • Swimming pool
  • •  Air conditioning
  • •  Pet Friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$86

Near Img And Siesta Key Beach Paradise Home

Oneco house

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$241

Privtate Siesta Key in-law Suit

Siesta Key private room

  • Beach / lakeside relaxation
  • •  Child Friendly
  • •  Air conditioning
  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$109

2Bedroom Beach Cottage - 3 Miles to Siesta Key

Gulf Gate Estates cottage

  • Pet Friendly
  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$63

Sarasota Downtown All Inclusive Town house !!!

Lido Key apartment

  • Child Friendly
  • •  Air conditioning
  • •  Pet Friendly
  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

Price per night from

$178

Light and Airy and Private, Great Location

Sarasota apartment

  • Air conditioning
  • •  Pet Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$172

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