Islamorada Pet Friendly Vacation Rentals
17 matching rentals.Most Popular
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Islamorada
This home is perfect for a family of 6 (or, for additional rent, accomodates a large family of 12, ask us how) wanting to enjoy breathtaking water views day or night! This house has an amazing 100 lineal ft deck facing ...
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per night
4 beds
4 baths
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Islamorada
Pelican Landing A 2-bedroom/2bath home, this hidden gem is located on Lower Matecumbe near mile marker 75. Step out the back of this house and enjoy the quiet serenity of this Lagoon front home. Need dockage? No problem...
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per night
2 beds
2 baths
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Islamorada
Located at Mile Marker 86.5 with 5 bedrooms, 3 Baths, this property sleeps 10-12. Gated estate home offers magnificent sunrises viewed from both 2nd and 3rd floor balconies. Plus sliding doors off the kitchen and addl u...
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per night
5 beds
3 baths
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Listings
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Islamorada
This home is perfect for a family of 6 (or, for additional rent, accomodates a large family of 12, ask us how) wanting to enjoy breathtaking water views day or night! This house has an amazing 100 lineal ft deck facing ...
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per night
4 beds
4 baths
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Islamorada
Welcome to paradise!
We are renting our beautiful house in Islamorada (Lower matacumbe key) You can't find a more quiet or peaceful neighborhood, safe for kids, perfect to walk your dog. Yet, you are only 3 - 5 miles a...
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per night
3 beds
2 baths
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Islamorada
SuCasa is one acre of land with two private homes and a one bedroom apartment. There is a 116 foot dock that can handle a large boat. It also has a 40 foot lagoon style fresh water swimming pool and a seven foot Jacuzzi...
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8 beds
5 baths
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Islamorada
This great 2 bedroom 2 bath home has a wonderful ocean view from the decks plus protected dockage. Located in Lower Matacumbe on the ocean side of the island. A wonderful private home that is affordable. Perfect for you...
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per night
2 beds
2 baths
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Islamorada
Pelican Landing A 2-bedroom/2bath home, this hidden gem is located on Lower Matecumbe near mile marker 75. Step out the back of this house and enjoy the quiet serenity of this Lagoon front home. Need dockage? No problem...
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per night
2 beds
2 baths
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Islamorada
Total seclusion in 10 unit oceanfront complex along millionaires row on Plantation Key, Islamorada, the Sport Fishing Capital of the World. Off the old highway, away from all the noise and traffic, yet walking distance ...
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per night
2 beds
2.5 baths
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Islamorada
Located on Lower Matecumbe, near mile marker 75, this charming little 2-bedroom/1 bath downstairs unit is perfect for a quiet getaway. Look out onto a large bayside lagoon, or lounge in the Jacuzzi after a long day of f...
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per night
2 beds
1 bath
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Islamorada
Large, quiet home located in exclusive Venetian Shores, MM86. Two story, 4 bd, 3 ba home on deep water canal with 70ft of dock space. Upstairs, 3 bd, 2 ba. with large open living, dining and kitchen space. Upstairs has ...
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per night
4 beds
3 baths
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Islamorada
Tropical Oceanfront Walled Estate. Protected Boat Basin, Deep Water, Great Views, Keys Living at it's Best.
This Property is located in the heart of Millionaires Row on Plantation Key, Islamorada. The House, cottage an...
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5 beds
5 baths
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Islamorada
Total seclusion in 10 unit oceanfront complex along millionaires row on Plantation Key, Islamorada, the Sport Fishing Capital of the World. Off old highway, away from all the noise and traffic, yet walking distance from...
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per night
2 beds
2 baths
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Islamorada
Escape the bustling crowds of Florida by renting this spacious vacation rental in Islamorada for your vacation in Florida. A two bedroom two bath private house in a tranquil residential locality of Venetian Shores, this...
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per night
2 beds
2 baths
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Islamorada
Located at Mile Marker 86.5 with 5 bedrooms, 3 Baths, this property sleeps 10-12. Gated estate home offers magnificent sunrises viewed from both 2nd and 3rd floor balconies. Plus sliding doors off the kitchen and addl u...
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per night
5 beds
3 baths
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Islamorada
This home is located in Islamorada in prestigious Venetian Shores at Mile Marker 86 on the bay side. This luxurious property has 5 bedrooms and 5 bathrooms, over 4200 sq ft under air, extensive outdoor covered spaces an...
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per night
5 beds
5 baths
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Islamorada
Very Private 4000 square foot home on water. Located in an exclusive area of all waterfront homes. This immaculate two-story home offers a luxurious and private setting. Five large bedrooms, four with kings, one with a ...
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per night
5 beds
3 baths
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Islamorada
The focal point of this spacious Florida Keys vacation home is its great room. kitchen stainless steel appliances, wine cooler, wet bar, dining room and living room combined, all looking looking out over the kidney shap...
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per night
2 beds
1 bath
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Islamorada
This great Bay Side pool home is located in Islamorada and has everything you would want for a perfect vacation. 3 bedrooms, heated pool, dockage, chickee, there is even a ground level game room with a pool table, foosb...
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per night
3 beds
3 baths
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Islamorada
King Fisher. High Speed DSL! Welcome, this lovely 3-bedroom home in Safety Harbor, on Lower Matecumbe. This home features spacious living areas, with very comfortable furnishings protected dockage for boats up to 35 ft,...
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per night
3 beds
2 baths
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Blog Posts
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September 04, 2012
Today, the guys made plans to go jet skiing for an hour in Islamorada, about 30 minutes north, so us girls took Travis to Theater of the Sea to see an assortment of shows. While there, we took a ride...
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August 03, 2012
On a recent trip, my favorite slice came from Ma's on Islamorada, one of the upper Keys. Ma's isn't a fancy restaurant; officially it's a fish camp but don't let that distract you. Ma's serves the pi...
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July 24, 2012
Last week, my teacher friends and I decided to take an impromptu trip to the Tiki Bar in Islamorada (Holiday Isle) near the Middle Keys. We were surprised by the fact that this was no longer a "public...
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July 14, 2012
On Tuesday, July 10, 2012, I ate lunch at Ma's Fish Camp located at 105 Palm Avenue, Islamorada, FL 33036. The place was, as my mom says, "Keysey". It had nice paintings for sale by local artists hang...
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June 14, 2012
Father's day is Sunday! My son and i are taking daddy to Anna Maria Saturday followed by a seafood feast! If we play our cards right we may shuttling off from Anna Maria to Shell Key, now that is a...
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April 01, 2012
I don't know if you've been reading my blog for this long, but when we left Miami last year in January, I got it in my head to see Stiltsville, houses built out in the flats on the eastern edge of Bis...
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November 23, 2011
Smart tarpon like to hang out at Robbie's Pier in Islamorada, in the Florida Keys. They hang out at Robbie's because this is where people come to feed them. For $3, you can get a bucket of small dead ...
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February 08, 2011
I had the pleasure to visit the Florida Keys last week and get out of the miserable cold that blasted into Colorado, while Josh and I were there, we visited two State Parks for hiking and snorkeling. ...
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March 06, 2010
It was in just such a spot that my husband Jay and I stopped to photograph a at sunset. So, it happened that we approached Islamorada near dark, when the sunset afterglow had disappeared into the wav...
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May 23, 2009
Is there anyone out there old enough (like me) to remember the classic movie “The Long, Long Trailer,” starring Lucille Ball and Desi Arnaz? Well, for the young pups, let me explain. The storyline cen...
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