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Dog Friendly Vacation Rentals in Siesta Key - FlipKey

420 pet friendly beach rentals in Siesta Key

Siesta Key 2 Bedroom 1 Bath Modern/Contemporary Decor Apartment

Siesta Key apartment

  • Beach / lakeside relaxation
  • •  Nearest beach 1 mi
  • •  Child Friendly
  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Amazing!” I stayed here with my husband and we had a great time! We were in Orlando visiting family and we decided to arrange some us time. The condo was excellent and very clean! Kathy and her husband were very informative, respond quickly,and available when we needed them. What was great was that we had all beach items available to us and were very useful. We were in close proximity to everything and the beach and restaurants were great! Everyone in the area was very friendly and my husband and I want to definitely come back!

Price per night from

$178

"Cottage by the Sea" 1 Bedroom/ 1 Bath Across From Beach!!- · 3031, 3032

Siesta Key cottage

  • Child Friendly
  • •  Pet Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$171

Walk to Siesta Beach, Heated Pool, Wifi, Fido friendly, Renovated Ground Floor U

Siesta Key apartment

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

Price per night from

$100

Fido Friendly, Saltwater Pool, Only 1 mile to SK Beach, Close to the Village, Sh

Siesta Key house

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

Price per night from

$182

3 Bedroom/ 2 Bath unit across from Siesta Key Beach Access.- Islamorada

Siesta Key apartment

  • Swimming pool
  • •  Child Friendly
  • •  Car not necessary
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$204

LJ's "Rustic Cottage"-- 2 Bedroom/ 2 Bath Steps From The Sand With Pool Access!!

Siesta Key apartment

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

Price per night from

$182

Seagrove

Siesta Key house

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

Price per night from

$126

Sandy Toes Siesta Key Florida (6796)

Siesta Key house

  • Beach / lakeside relaxation
  • •  Nearest beach 0 mi
  • •  Swimming pool
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Fantastic!!!” Loved it!!! This place was very clean, close enough to beach, very spacious, tastefully decorated with upgrades, decent pool, a manager on site, and more beach gear than you could ask for. ...Chairs, games, rafts, umbrellas, bikes, towels, coolers, etc. we absolutely loved it!!! We had a family of 6....Parents and 4 teenagers. We also liked that across the street was convenience stores, grocery, and restaurants. The Toasted Mango and The Fish Market have great, great food. Also, our flight was canceled to fly in, and they were out of rental cars at newly appointed airport. How relieving it was to finally show up to such a nice place and relax The owner was also so very kind to accommodate us if needed.

Price per night from

$344

5 Bedroom Beachfront Home on Siesta Beach!! 49 Beach Rd

Siesta Key house

  • Child Friendly
  • •  Car not necessary
  • •  Air conditioning
  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

Price per night from

$617

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

Siesta Key hotel apartment

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

Price per night from

$98

The Shells Villa - Next to Beach & Village

Siesta Key house

  • Beach / lakeside relaxation
  • •  Nearest beach 0 mi
  • •  Child Friendly
  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

“Great Experience and Location!” We could not have been happier with our Experience at Shell Villa. Location to the Village was super close as described. Access to the beach was great both through the private walkway or the public access about two block away. The house was well stocked and the floor plan was perfect for our two families. Best place I have rented on SK in 5 years.

Price per night from

$245

Just Minutes from the White Sandy Siesta Beach

Siesta Key condo

  • Nearest beach 4 mi
  • •  Swimming pool
  • •  Child Friendly
  • 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.

Price per night from

$79

Private Siesta Key House - Walk to Village & Beach - Heated Pool/Spa - No Stairs

Siesta Key house

  • Nearest beach 1 mi
  • •  Swimming pool
  • •  Child Friendly
  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“Fantastic house close to everything” We stayed in Siesta key for the first week of November. This house was beautiful and equipped with everything you could ever need especially the heated pool and hot tub. we walked a block every evening to the village and every morning two blocks to the beach. Will book again for sure

Price per night from

$269

10% Holiday Sale - Dec. 2019: Luxurious 2 BR Condo - Short Walk to Siesta Beach

Siesta Key apartment

  • Beach / lakeside relaxation
  • •  Nearest beach 0.2 mi
  • •  Swimming pool
  • 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.

Price per night from

$130

5 minute walk to Siesta Key Beach and Village!

Siesta Key house

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$171

Grand White Sands 303 - Walk to beach and village

Siesta Key condo

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

Price per night from

$124

Sandy Toes Siesta Key Florida (6798)

Siesta Key house

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

“Very good” It's was great stay ,close to the beach (3-5)min walk,private,quite for vacation location. Car was parked in the garage and we loved it !!! Also you have everything you possibly need in a kitchen !! And condo has everything you need to go to the beach too !!(beach chairs,umbrellas,towels ....Will stay again Thank you Kathey and Joe

Price per night from

$344

Cape Aqua

Siesta Key house

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

“Great place, super location” We thoroughly enjoyed our stay at your home. It was very spacious, clean and inviting. We had everything we needed and the location is wonderful. Thanks and we would definitly recommend your home to others

Price per night from

$142

******* Canal Rd- Awesome village location!

Siesta Key condo

  • Swimming pool
  • •  Child Friendly
  • •  Car not necessary
  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$395

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

Beach Place - Seahorse Cottage - Peak of the Gulf, 30 Seconds to the Sand

Siesta Key cottage

  • Nearest beach 0 mi
  • •  Swimming pool
  • •  Child Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$164

Big Pass Hideaway

Siesta Key house

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

Price per night from

$276

The Treehouse

Siesta Key house

  • Child Friendly
  • •  Air conditioning
  • •  Pet Friendly
  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$453

Renovated 2 bedroom with beach views and pool access!!-Living the Dream, Mermaid

Siesta Key apartment

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$217

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

Tiny House Siesta - Yellow Lifeguard Stand Tiny House

Siesta Key hotel apartment

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

Price per night from

$102

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • Beach / lakeside relaxation
  • •  Swimming pool
  • •  Child Friendly
  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Price per night from

$999

Darling 1 Bedroom/ 1 Bath with private patio and 1 block to village!!- VH Island

Siesta Key apartment

  • Child Friendly
  • •  Pet Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$171

Cute 2Bedroom/1Bath Cottage- Across from Siesta Key Beach Access-Cottage by Sea

Siesta Key cottage

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

Price per night from

$194

Tiny House Siesta - Tiny House Amy

Siesta Key house

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

Price per night from

$102

Tiny House Siesta - Red Lifeguard Stand

Siesta Key house

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

Price per night from

$98

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

Siesta Key hotel apartment

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

Price per night from

$86

1 Block from Siesta Key Beach, Free Wifi w/ Private Optional Heated Pool, Near S

Siesta Key house

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

Price per night from

$158

A Siesta Tropical Retreat - Island Pool Oasis

Siesta Key house

  • Beach / lakeside relaxation
  • •  Nearest beach 0.64 mi
  • •  Swimming pool
  • 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!

Price per night from

$144

Banana Cabana-Steps to the Beach!! 539 Beach Rd

Siesta Key condo

  • Child Friendly
  • •  Car not necessary
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$228

Directly Across from Siesta Beach with Gulf Views & Steps from Village!-LTD Star

Siesta Key apartment

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$217

Key West Suite next to Siesta Key Beach

Siesta Key apartment

  • Beach / lakeside relaxation
  • •  Nearest beach 0.01 mi
  • •  Swimming pool
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Awesome property and location!” Our 3 teenagers loved the beach right across the street and taking the trolley to the Village. Our 5 year old lived in the beautiful pool. The kitchen was fully equipped and the unit was impeccably clean. A bonus was the use of beach toys, chairs and umbrellas. We'll definitely stay at Gumbo Limbo again.

Price per night from

$289

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

Siesta Key hotel apartment

  • Nearest beach 1 mi
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$109

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