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Dog Friendly Vacation Rentals in Islamorada - FlipKey

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71 pet friendly house rentals in Islamorada

Oceanfront Oasis - Pinch me am I dreaming!!!

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 7 minutes

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Price per night from

$6,191

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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$430

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

$667

LYONS LANDING

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$263

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 3 minutes

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Price per night from

$575

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

$430

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 25 minutes

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Price per night from

$1,261

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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$194

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$792

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

$188

MANATEE MANOR

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$199

Fabulous 6bedroom /4bathroom Waterfront Pool Home in Islamorada - 3/2 Each Level

Islamorada house

3 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 33 minutes

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Price per night from

$382

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 25 minutes

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Price per night from

$1,261

Conch & Lobster Homes

Islamorada house

5 bedrooms / 5 bathrooms / sleeps 14

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$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 25 minutes

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Price per night from

$1,261

Recently Remodeled Beautiful Pool Home with Private Dock with Beach Access

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$421

Beautiful Pool Home with Private Dock with Beach Access

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$403

Islamorada Florida Cozy Cottage

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 4

Responds fast! avg. 2 hours 8 minutes

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Price per night from

$327

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. 31 minutes

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Price per night from

$202

Little Bay Upper Level

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$492

Keys Kottage / Bayside

Islamorada villa

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$278

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

$273

Great rentals within 20 miles that match your search

MM88 Best Keys Location Tranquil Wooded

Tavernier house

1 bedroom / 2 bathrooms / sleeps 8

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Price per night from

$143

The Eagle's Nest

Tavernier bungalow

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$163

Key Largo Beautiful House

Key Largo house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 27 minutes

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Price per night from

$288

Key Largo Ocean Front Villa with Dock and Incredible views

Key Largo villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 38 minutes

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Price per night from

$458

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. 57 minutes

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Price per night from

$78

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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Price per night from

$190

Dockside Condo and Boat

Key Largo apartment

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 56 minutes

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Price per night from

$370

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Price per night from

$211

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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$142

Waterfront Home w/EZ Ocean Access*Boat Slip*Roof Top Deck*Hot Tub*28 nt min

Key Largo house

3 bedrooms / 4 bathrooms / sleeps 6

“Great Key Largo Rental” We rent homes on the water in the Keys frequently. By far this is the best home we have rented. House is immaculate, fully equipped,and only a short ride to the ocean. On water gas super close. Restaurants within walking distance. Management company is awesome, very responsive and prompt.

Responds fast! avg. 55 minutes

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Price per night from

$205

Sunrise Waterfront Home

Key Largo house

4 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$287

Viewing 38 of 71
rentals in Islamorada

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