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Dog Friendly Vacation Rentals in Islamorada - FlipKey

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64 pet friendly house rentals in Islamorada

Oceanfront Oasis - Pinch me am I dreaming!!!

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 56 minutes

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Price per night from

$6,183

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

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. 14 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

$292

FLAMINGO COTTAGE

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

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$117

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 51 minutes

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Price per night from

$982

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

Paradise Beach Sandy Oceanfront

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 55 minutes

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Price per night from

$1,473

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

$209

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

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Price per night from

$573

Alligator Reef - Conch Home

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$733

ANTIGUA PLACE

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$207

MANATEE MANOR

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$215

San Roc - Private 150 Ft Oceanfront 2.5 Acre Millionaire Row Estate, Pool, Spa,

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 55 minutes

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Price per night from

$1,473

Conch & Lobster Homes

Islamorada house

5 bedrooms / 5 bathrooms / sleeps 14

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Price per night from

$916

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

Islamorada house

5 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 1 hour 55 minutes

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Price per night from

$1,473

Islamorada Florida Cozy Cottage

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 4

Responds fast! avg. 1 hour 45 minutes

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Price per night from

$344

Little Bay Lower Level

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$492

Relaxation in the Keys! MM 74 1/2

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 29 minutes

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Price per night from

$201

Little Bay Upper Level

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$492

Keys Kottage

Islamorada villa

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$269

Little Bay Compound

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 18

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Price per night from

$1,473

3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.

Islamorada apartment

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$271

Islamorada trop paradise pool, fishing, 2fls luxury with a filet stationn

Islamorada house

4 bedrooms / 2 bathrooms / sleeps 14

Responds fast! avg. 1 hour 9 minutes

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Price per night from

$401

New Listing! Luxury Oceanfront Estate in Islamorada - Booked until August 2022

Lower Matecumbe Key house

6 bedrooms / 7 bathrooms / sleeps 14

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Price per night from

$1,554

Majestic estate, 200' of private oceanfront beach & pool, ideal wedding venue

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$1,472

Great rentals within 20 miles that match your search

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 5 minutes

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Price per night from

$92

Waterfront Home In Florida Keys

Tavernier house

2 bedrooms / 2 bathrooms / sleeps 4

“Perfect Holiday in Tavernier” We had a wonderful time at Dan and Penny's home. They were very accommodating! The home is absolutely pristine and in a nice neighborhood. There wasn't a day that we did not see manatee and tarpon in the canal in front of the house. Perfect location for restaurants, shopping and activities either by land or water. Beautiful home with everything you need for a perfect vacation in the Keys!

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$192

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 55 minutes

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Price per night from

$207

Private Beachfront -Perfect for Families and Events Historic Shadow Point Estate

Key Largo house

6 bedrooms / 5 bathrooms / sleeps 16

“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.

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Price per night from

$2,061

Key Largo Rental Fantastic Views

Key Largo condo

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 24 minutes

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Price per night from

$344

Key Largo Ocean Front Villa with Dock and Incredible views

Key Largo villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 24 minutes

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Price per night from

$573

Sunrise Waterfront Home

Key Largo house

4 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$287

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

$144

Cozy Couple Getaway! or Great Family Home

Key Largo house

2 bedrooms / 1 bathroom / sleeps 5

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Price per night from

$144

Unique Houseboat on Dry Lot

Key Largo houseboat

2 bedrooms / 1 bathroom / sleeps 6

“Quaint and unique rental” The houseboat was everything I expected and needed it to be. It slept our family of four comfortably - which was all we really needed. The weather was good so really the only thing we did at the houseboat was shower and sleep. We did also do a few loads of wash - having a full size washer and dryer was convenient. I bet if we spent more time there, we would have used the back yard, it is really neat and welcoming. Maggie was a gracious hostess and everything was exactly where and how she described it. All in all a great value.

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Price per night from

$144

MM88 Best Keys Location Tranquil Wooded

Tavernier house

1 bedroom / 2 bathrooms / sleeps 8

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Price per night from

$126

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