Dog Friendly Vacation Rentals in Longboat Key - FlipKey

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214 pet friendly apartments in Longboat Key

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Amazing Village Cottage! Walk to Whitney Beach!

Longboat Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Pets allowed

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Price per night from

$394

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

Match: Pets allowed

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Price per night from

$193

Great rentals within 20 miles that match your search

Beautiful Sunkst Cottage Bradenton Beach - AMI-Tropical Setting - Heated Pool

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Pets allowed

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Price per night from

$517

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Pets allowed

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Price per night from

$1,001

Luxury Beach Cotttage

Sarasota cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Beautiful little cottage” We stayed at this lovely little cottage on Siesta Key mid-April. The cottage is very nice, with all the amenities, even a washer/dryer for extended stays. It's cozy, with high ceilings, a nice bathroom and kitchen/living room. The bed seemed a little small (only a double), but it was very comfortable. The wireless internet was not working when we were there, which was a little frustrating. There is a beautiful pool and nice garden areas. The private beach was also very nice. All of the staff and the owner were extremely pleasant and welcoming. We enjoyed our time there.

Match: Pets allowed

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Price per night from

$533

AnnaMariaIsland a Paradise. MINUMIM RENTAL 2 WEEKS

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 22 minutes

Match: Pets allowed

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Price per night from

$197

Gorgeous views,spectacular home!

Anna Maria house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

“Majestic Views” Our family loved our visit to Anna Maria. The house is gorgeous and spacious. My kids enjoyed the pool and eating outside. We hope to return in the near future.

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Price per night from

$631

Jacaranda Artist Retreat

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Pets allowed

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Price per night from

$218

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.

Match: Pets allowed

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Price per night from

$166

Sandy Toes Town Home

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Time in Paradise” We recently had the luck to spend two months in paradise. This condo was comfortably appointed, well stock to meet all our needs, and most importantly in the perfect location. The beach was a short walk to the left and stores and restaurants were just a short walk to the right. We had a great time and enjoyed everything Sarasota, Siesta Key, and this Sandy Toes Condo had to offer. Thanks Mark!

Match: Pets allowed

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Price per night from

$273

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!

Match: Pets allowed

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Price per night from

$501

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Price per night from

$230

Three bedroom house directly on beach with gulf vi

Siesta Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

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Price per night from

$402

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Price per night from

$107

BAY FRONT HOUSE WITH PRIVATE DOCK

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 31 minutes

Match: Pets allowed

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Price per night from

$345

Luxury Sarasota Golf Home

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$369

Light and Airy and Private, Great Location

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Pets allowed

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Price per night from

$230

CKBH (Casey Key Beach House)

Osprey house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Pets allowed

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Price per night from

$655

Downtown Sarasota Historic Burns Court Adorable Bungalow

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Pets allowed

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Price per night from

$295

Captiva Paradise Home close to IMG Academy & Siesta Key Beach

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 9 minutes

Match: Pets allowed

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Price per night from

$373

Sarasota Downtown All Inclusive Town house !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

Responds fast! avg. 1 hour 46 minutes

Match: Pets allowed

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Price per night from

$190

Vacation Sarasota in great location to all venues....

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Pets allowed

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Price per night from

$229

Casey Key 1-Bed Villa #2

Nokomis villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Pets allowed

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Price per night from

$172

Casey Key 2-Bed Dockside Penthouse

Nokomis penthouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Pets allowed

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Price per night from

$206

Sarasota Downtown, Best Location For Your Vacation !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Responds fast! avg. 1 hour 46 minutes

Match: Pets allowed

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Price per night from

$194

Tiny House Siesta - Yellow Lifeguard Stand Tiny House

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Pets allowed

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Price per night from

$423

Tiny House Siesta - Red Lifeguard Stand

Siesta Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Pets allowed

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Price per night from

$443

Tiny House Siesta - Eleanor- our bright & beautiful Tiny House near the beach

Siesta Key hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Pets allowed

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Price per night from

$448

Tiny House Siesta - Tiny House Amy

Siesta Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Pets allowed

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Price per night from

$378

Tiny House Siesta - Tiny Blue Oasis – a tiny house with 3 Queen beds

Siesta Key hotel apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Pets allowed

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Price per night from

$460

Tiny House Siesta - Tiny Aqua Oasis- Tiny House that sleeps 6 comfortably

Siesta Key hotel apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Pets allowed

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Price per night from

$444

Tiny House Siesta - Sand Dollar – A private master loft and open living space

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Pets allowed

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Price per night from

$448

Oceanfront home w/sunset views of Sarasota Bay

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Pets allowed

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Price per night from

$630

Just Minutes from the White Sandy Siesta Beach

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“It was very cozy and comfortable apartment!” We loved to spend our vacation at this place. Really close to the beach, to different restaurants, and all kind of stores.

Match: Pets allowed

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Price per night from

$115

LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Pets allowed

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Price per night from

$161

Water View, 100 Fishing Dock! Teton 40 Ft. Trailer W/3 Slide Outs

Palmetto house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Pets allowed

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Price per night from

$138

Gorgeous Waterfront Apartment Steps From 100Ft Fishing Dock And Tiki.

Palmetto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Pets allowed

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Price per night from

$167

Very Rare! Adorable Cottage on Snead Island, Boat Dock & Beach 250 ft.

Palmetto house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Pets allowed

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Price per night from

$167

Viewing 38 of 214
rentals in Longboat Key

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