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Pets allowed
Parking
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Non-Smoking property
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Beach or lakeside relaxation
Skiing – property near ski resort
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45 pet friendly house rentals in Islamorada

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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. 1 hour 0 minutes

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Price per night from

$670

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. 1 hour 47 minutes

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Price per night from

$982

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

4 bedrooms
4 bathrooms

sleeps 10

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Price per night from

$802

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

Islamorada house

5 bedrooms
4 bathrooms

sleeps 12

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Price per night from

$1,260

Cozy Keys Cottage Islamorada FL.

Islamorada house

3 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$408

Keys Kottage

Islamorada villa

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$315

The Nest Villa and Marina at Holiday House Resort, Islamorada

Upper Matecumbe Key villa

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$343

New Upscale, private pool, Dockage, kayaks, bikes, downtown Islamorada locale

Islamorada house

3 bedrooms
4 bathrooms

sleeps 6

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Price per night from

$911

Majestic estate, 200' of private oceanfront beach & pool, 3,600sqft tiki

Islamorada house

3 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$1,472

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

Islamorada house

4 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$784

Boater's Paradise

Lower Matecumbe Key house

4 bedrooms
3 bathrooms

sleeps 10

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Price per night from

$377

Great rentals within 20 miles that match your search

Cozy Couple Getaway! or Great Family Home

Key Largo house

2 bedrooms
1 bathroom

sleeps 4

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Price per night from

$103

Unique Houseboat on Dry Lot Family and Pet Friendly

Key Largo houseboat

2 bedrooms
1 bathroom

sleeps 4

“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

$98

Large Waterfront 4 balcony Key Largo Townhouse with Oceanfront Dock

Key Largo townhouse

3 bedrooms
3 bathrooms

sleeps 8

Responds fast! avg. 2 hours 45 minutes

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Price per night from

$401

Diving, Fishing, Snorkeling, Kayaking Paradise

Key Largo townhouse

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 45 minutes

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Price per night from

$401

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!

Responds fast! avg. 1 hour 17 minutes

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Price per night from

$210

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

$247

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

$2,405