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Dog Friendly Vacation Rentals in Florida Keys - FlipKey

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160 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

$105

PARADISE OCEAN FRONT HOME

Marathon house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 56 minutes

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Price per night from

$628

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

$332

Duck Key 50% off October

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 4 minutes

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Price per night from

$656

Villa Sombrero, Marathon

Marathon house

5 bedrooms / 4 bathrooms / sleeps 10

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Price per night from

$652

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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Price per night from

$143

Spacious Top Floor Condo w/ Water View!!

Marathon apartment

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$371

Key West Island Vacation

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 14 minutes

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Price per night from

$478

Family Retreat-Ocean front home with private pool

Cudjoe Key house

6 bedrooms / 4 bathrooms / sleeps 14

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Price per night from

$685

Oceanfront Oasis - Pinch me am I dreaming!!!

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 10

Responds fast! avg. 1 hour 38 minutes

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Price per night from

$2,863

Catch of the Day!

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$125

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

$250

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$113

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

Big Pine Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 48 minutes

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Price per night from

$228

Fandango

Cudjoe Key house

5 bedrooms / 3 bathrooms / sleeps 14

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Price per night from

$685

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. 25 minutes

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$126

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!

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Price per night from

$571

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. 25 minutes

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Price per night from

$668

LYONS LANDING

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$292

East Sister Rock Island

Marathon Shores house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$2,037

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

Tavernier house

3 bedrooms / 3 bathrooms / sleeps 12

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Price per night from

$246

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

Marathon Shores house

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 17 minutes

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Price per night from

$340

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

Marathon villa

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 23 minutes

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Price per night from

$356

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. 3 hours 28 minutes

Match: Pets allowed

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Price per night from

$978

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

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

$516

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

$428

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

$214

SUNSHINE PLACE

Islamorada villa

1 bedroom / 1 bathroom / sleeps 3

“a jewel worth the search” Dog friendly, spacious location for relaxing or as a base for exploring the upper/middle keys. The property is shoehorned between two resorts, but surprising quiet and even secluded, in a way. Plenty of people-watching available, but sunrise it's just you, the pelicans, warblers and ospreys. Yes, there is an active osprey nest over the driveway/parking area.

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Price per night from

$214

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

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Price per night from

$571

Hogfish Retreat

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$177

New Listing Family Friendly

Key West townhouse

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$365

LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!! SLEEPS 2-4, 3 BLKS TO BEACH

Key West apartment

1 bedroom / 1 bathroom / sleeps 4

“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. 2 hours 50 minutes

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Price per night from

$181

CONCH BAR SOUTH

Tavernier house

4 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$367

Key Largo Beautiful House

Key Largo house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 7 minutes

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Price per night from

$251

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

Marathon villa

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 23 minutes

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Price per night from

$356

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