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Dog Friendly Vacation Rentals in Florida Keys - FlipKey

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251 pet friendly house rentals in Florida Keys

Conch Haven Old Town 1/1 MONTHLY Rental

Key West apartment

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$79

PARADISE OCEAN FRONT HOME

Marathon house

4 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$327

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

Marathon Shores house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$285

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Price per night from

$308

Magnificent Ocean view with 35' dock , Canal home in gated Venture Out Resort

Cudjoe Key cottage

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$184

Duck Key Paradise

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 1 hour 51 minutes

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Price per night from

$590

Villa Sombrero, Marathon

Marathon house

5 bedrooms / 4 bathrooms / sleeps 10

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Price per night from

$650

Conch Key Villas Unit 1, Quiet, Clean with Awesome VIews in Paradise

Conch Key apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 22 minutes

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$189

Key Largo Kampground Vacation

Key Largo house

1 bedroom / 1 bathroom / sleeps 3

“Great location and pleasantly surprised!” Romberto's Camprground vacation was definitely more than i expected. There was ample room for my husband and I, the folks were nice and the area was quiet and clean. The marina was convenient (small boats only). There was a small leak in the bathroom in the overhead skylight but it was almost negligible unless it was pouring. we will definitely be back.

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$144

75130 Overseas Highway

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 4

“The view and location was excellent.” The house had most of the amenities I would expect at a beach location. You can't beat the sunsets over the bay! We snorkeled at Key Largo and took a day trip into key West, so the location was perfect. The area had the best restaurants. We tried them all. Only complaints were: no outdoor grill, no wine glasses, sheets kept pulling off the bed and rusted beach chairs.

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Price per night from

$247

Spacious Top Floor Condo w/ Water View!!

Marathon apartment

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$365

Key West Island Vacation

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$547

Welcome Aboard! Relax, unwind, enjoy the water! in key west

Key West yacht

4 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$326

Family Retreat-Ocean front home with private pool

Cudjoe Key house

6 bedrooms / 4 bathrooms / sleeps 14

Responds fast! avg. 3 hours 18 minutes

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Price per night from

$691

Oceanfront Oasis - Pinch me am I dreaming!!!

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 53 minutes

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Price per night from

$6,213

A quiet spot in paradise close to fishing with dockage included (#4)

Conch Key villa

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 21 minutes

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Price per night from

$186

Catch of the Day!

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$120

LITTLE BAY - Upper Duplex

Islamorada villa

2 bedrooms / 2 bathrooms / sleeps 6

“Classic Islamorada - Amazing Property” Little Bay was a perfect property for us! The setting is idyllic and classic keys - Huge backyard on the Bay with excellent dock area, hammocks and view of the bay. Covered porch was the full width of the house and was a great place to hang out morning and evening. The property had everything that we needed, was centrally located and have plans to visit again! Service provided by rental agency was top notch and very attentive - they showed us around, accepted packages on our behalf and were friendly and helpful throughout our entire rental experience - from planning to checkout. This is definitely on our To Re-Do List.

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Price per night from

$429

TWICE THE CHARM

Key Largo house

4 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$183

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 55 minutes

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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

Responds fast! avg. 1 hour 21 minutes

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$198

Fandango

Cudjoe Key house

5 bedrooms / 3 bathrooms / sleeps 14

Responds fast! avg. 3 hours 18 minutes

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Price per night from

$688

Waterfront in Key Largo, Terrific 1/1 Apt, 2nd Floor, Pet Friendly, Sleeps 4

Key Largo apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 45 minutes

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$79

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!

Responds fast! avg. 3 hours 18 minutes

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Price per night from

$533

Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

“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. 16 minutes

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Price per night from

$670

LYONS LANDING

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$262

East Sister Rock Island

Marathon Shores house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$1,548

Clean Keys 3/3 w/Davits Clear Canal Bay Side/Views Fenced 2Level Tavernier Home

Tavernier house

3 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$207

Paraidise with or witout boat

Marathon Shores house

2 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 10 minutes

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Price per night from

$315

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

Marathon villa

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 59 minutes

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Price per night from

$1,151

MY PARADISE

Layton house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$275

FLAMINGO COTTAGE

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$117

LITTLE BAY - Lower Duplex

Islamorada villa

2 bedrooms / 2 bathrooms / sleeps 6

“Beautiful House in the heart of Islamorada” My kids and I stayed on the property and rented the lower duplex. We had an amazing time and the dock for our boat was perfect. The kids and I went paddleboarding right off the back of our house and the dog also loved the large yard. The kids could snorkel right out back and it was located right next to everything. We never used our car to get around since we had the boat right in our back yard. We will most certainly be back.

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Price per night from

$429

102 Columbus Drive

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 4

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$126

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

Key West townhouse

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$513

Key West Gulf front Home with private dock and pool.

Key West house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$326

Paradise Beach Sandy Oceanfront

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 25 minutes

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Price per night from

$1,374

Kokomo Cove Boat House

Marathon house

2 bedrooms / 2 bathrooms / sleeps 8

“Boat ramp and beautiful pool in the heart of the Keys” We wanted a house on a canal in the Marathon area, where we have been vacationing for years. This house had its own boat ramp, so we rented kayaks for a week and launched effortlessly right on site. The pool is lovely and relaxing. The house is well equipped and centrally located so trips up to Key Largo and down to Key West are quick.

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Price per night from

$183

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