Dog Friendly Vacation Rentals in Florida Keys - FlipKey

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140 pet friendly house rentals in Florida Keys

Conch Haven Cottage Old Town Studio MONTHLY Rental

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Pets allowed

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Price per night from

$108

PARADISE OCEAN FRONT HOME

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Pets allowed

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Price per night from

$1,034

FL Keys Waterfront Pool Home 2 Bedrooms Sleeps 6 w/ 60 Feet of Dockage

Marathon Shores house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Pets allowed

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Price per night from

$288

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Price per night from

$334

Duck Key 50% off October

Duck Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Pets allowed

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Price per night from

$661

Villa Sombrero, Marathon

Marathon house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Pets allowed

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Price per night from

$657

Spacious Top Floor Condo w/ Water View!!

Marathon apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Pets allowed

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Price per night from

$373

Key West Island Vacation

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Pets allowed

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Price per night from

$482

Family Retreat-Ocean front home with private pool

Cudjoe Key house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

Match: Pets allowed

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Price per night from

$794

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Pets allowed

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Price per night from

$114

New Listing! Beautiful Canal front , Key Deer and jacuzzi.

Big Pine Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Pets allowed

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Price per night from

$288

Fandango

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Match: Pets allowed

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Price per night from

$756

Tropical Paradise Oceanfront Home with Pool

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“The Perfect Little Get away” We (my husband and I and our 1 year-old) stayed at the Tropical Paradise Home for a week with another couple; and it was the perfect amount of space to enjoy each other's company but still have our own private areas. The house was very, very clean when we checked in and we immediately felt at home. The pictures we had seen on-line did accurately reflect the rental's and amenities. The kitchen was great and we ate most of our meals on the screened in porch. We felt very secluded at the end of the street in our own tropical paradise. The vegetation and landscaping around the house is so beautiful. We all enjoyed time reading in the hammock, kayaking from our own backyard, and cooling off in the pool. We also enjoyed the beautiful sunrise every morning thanks to the baby. :) The owner is very friendly and left a packet of activities and restaurants near-by that she recommended. We enjoyed the restaurant Square Grouper for lunch or dinner (less than 5 mins away) and also enjoyed stand-up paddle boarding with sup Key West. We rented a full size crib from Baby Chick Rentals and they had the crib set up before we arrived. We also enjoyed driving into Key West for shopping/bars/and more restaurants. The drive to Key West is about 25 mins. We would definitely recommend the Tropical Paradise Home and we would stay there again!

Match: Pets allowed

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Price per night from

$575

“Comfortable home for family get-together” Positive experience overall: Our family of six adults had a tropical-feeling destination Christmas here. The house easily accommodated all of us, and we enjoyed the wrap-around porch and pool. We appreciated the commodious kitchen with a two-tier dishwasher and side-by-side refrigerator with ice/water dispenser. Having a washer and dryer on the premises was very helpful, since guests are requested to wash linens and towels before departing. Some drawbacks: the house did not come equipped with adequate staples, such as paper products, laundry detergent, and garbage bags, so be prepared to purchase these. There are no beaches or stores within walking distance. On a couple of nights, noisy neighbors talking on the street woke us up. (In general, though, the area is quiet.)

Responds fast! avg. 1 hour 0 minutes

Match: Pets allowed

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Price per night from

$673

East Sister Rock Island

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Pets allowed

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Price per night from

$2,209

Match: Pets allowed

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Price per night from

$248

Paradise with or without a boat Clean Waterfront Beach Near Pet free

Marathon Shores house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 57 minutes

Match: Pets allowed

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Price per night from

$345

Waterfront luxury Villa (34) with sunset views and boat slip

Marathon villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 30 minutes

Match: Pets allowed

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Price per night from

$300

SANCTUARY IN PARADISE

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“What Florida dreams are made of” Growing up in South Florida and the Keys but now moved farm away, I wanted to show my husband and young children the Florida I remembered as a child. This my friends was more than my dreams could have asked for! We were tremendously blessed to have had the opportunity to share this paradise! Private, gated estate with coral wooded hammocks to stroll through, palm trees clicking in the breeze, flocks of ibis that grazed through the lush green yard that ended at the private water front. Orchids blooming in the trees welcomed us to the hammocks where we had our morning coffee to stunning colored sunrises. It had everything: super clean Keys styled house with a cute kitchen (that saved us on meal expenses), bedrooms and bathrooms that were perfect size and accommodations, and wifi. It was quiet yet welcoming to my kids. We kayaked and swam on Christmas morning! The hosts were gracious and really made us feel as we were family. It was a Christmas we will always cherish. "Give and it will be given to you. A good measure, pressed down, shaken together and running over, will be poured into your lap." Luke 6:38 Truly, after giving us the chance to come share your slice of heaven, our cup runneth over.

Responds fast! avg. 2 hours 26 minutes

Match: Pets allowed

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Price per night from

$986

Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Pets allowed

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Price per night from

$920

Key West Gulf front Home with private dock and pool.

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Pets allowed

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Price per night from

$483

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Pets allowed

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Price per night from

$805

Hogfish Retreat

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Pets allowed

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Price per night from

$179

New Listing Family Friendly

Key West townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Pets allowed

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Price per night from

$368

“Fantastic Stay!” My husband and two sons (21 & 24) stayed in this condo over Christmas. This was our first stay in Key West and we wanted to be close to everything, but yet not right on Duval St. This location was perfect; literally a stones throw away from Duval St. The unit inside was decorated very lovely and had all the amenities one would need. I found the owners were nice to do business with, especially Deb who I mostly communicated with. My family and I enjoyed our stay in Key West immensely, we had so much fun! We met many very friendly people out and about town. We would love to visit again, if we do, we would like to stay in this condo or the Bella Vita, the owner's other condo.

Responds fast! avg. 14 minutes

Match: Pets allowed

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Price per night from

$285

Key Largo Beautiful House

Key Largo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Pets allowed

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Price per night from

$265

Waterfront luxury Villa (30) with sunset views and boat slip

Marathon villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 30 minutes

Match: Pets allowed

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Price per night from

$300

Match: Pets allowed

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Price per night from

$2,135

Ocean Side View on Canal, Great for Fishing, Near Sombrero Beach & Restaurants

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Pets allowed

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Price per night from

$690

Waterfront luxury Villa (59) with sunset views and boat slip

Marathon villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Awesome” Our stay at Indigo Reef was excellent. The unit is everything we hoped it would be. We would definitely return.

Responds fast! avg. 1 hour 30 minutes

Match: Pets allowed

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Price per night from

$300

Blue Dolphin Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool

Islamorada house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Pets allowed

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Price per night from

$1,145

“Fantasic wedding on paradise!!” We picked Shadow Point because of it's fabulous secluded view and beautiful gardens on 2.5 acres. The house and cottage held up to 16 of us and was wonderfully decorated with period antiques. Our guests loved playing at their beach and kayaking and swimming around Key LargoSound. Our wedding was perfect with the full moon rising over our reception. We danced the night away in paradise.

Match: Pets allowed

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Price per night from

$2,414

Private Key Largo Bayside Canalfront home

Key Largo house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Pets allowed

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Price per night from

$202

Manatee Bay

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Pets allowed

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Price per night from

$151

Island Chalet

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Pets allowed

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Price per night from

$161

Blue Lagoon

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Pets allowed

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Price per night from

$319

"Gulfside Grouper", Waterfront-Ground floor, 60' Dockage, Pool/Hot Tub, Pets OK

Marathon Shores house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Pets allowed

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Price per night from

$986

Conch Out

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Pets allowed

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Price per night from

$194

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