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Houses Islamorada

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148 houses

75731 Overseas Highway

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

“Vacation of a lifetime!” I can't say enough good things about this home. It was beautiful, clean, and peaceful. The only thing that might be considered a down side is that all of the bedrooms are located upstairs, but that was not a problem for us. Brandi at Freewheeler Realestate was wonderful. She was prompt with answers to questions, friendly and professional. The home-owner obviously wants to see to it that the people staying in their home are well taken care of. Everything was great all the way down to the fluffy beach towels. We will definitely look at staying at this home again.

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$1,227

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

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$1,719

76004 Overseas Highway

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 8

“Wonderful accommodations” Aside from being rainy for the majority of our stay, the accommodations were amazing. We will certainly be going back to this house. This house sleeps 8-10 adults comfortably. Freewheeler Realty was a pleasure to do business with and was the only company that was responsive to my inquiries. The house has an amazing view, full laundry, kitchen upstairs and downstairs. My favorite part were the stairs that go directly into crystal clear water to snorkel!

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$328

100 Palo De Oro Drive

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

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$430

132 Columbus Drive

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 4

“Fantastic getaway” This is a great vacation rental property for a couple or small groups of 4 or less people. First of all, you can't beat the panoramic view of the water and what's more, the water is just 10 ft away. The front yard is one of the best if not the best with a lot of gardening and the antiques placed in the garden easily beats the boring gnomes. The interior of the house has a very wood cabin like feel to it and if you're looking for modern furniture, you'll be disappointed but if you're into a quaint little cottage like atmosphere, this will not disappoint. The 2 bedrooms are well kept and there are tons of pictures on the wall from the owners' travels all over the world and they're very interesting. There is no flat screen TV but the old color TV is more than sufficient - it has cable with most big channels you'll need (no premium ones except maybe Encore). They also have a ton of Dvds and Music CDs for your entertainment if you ever get bored of the views from the wrap around deck :-) The sunrises from this deck are awesome if you can wake up early - no sunsets cuz that's on the other side but you can always walk/drive over to the Overseas highway within minutes to catch the sunsets from there. The other amenities worth mentioning are the inground hot tub/spa they have which was awesome - you can view the ocean from the spa. If that wasn't close enough a view, you can pick up the huge Kayak they have and walk right into the water and row away. If there was any drawback, it was these bugs called no-see-ums that come out in full force in the evenings and if you aren't taking necessary protection, they will wreak havoc on your skins, but the owners/realtors can't do much about this. Just get some Off spray or something and you'll be fine. Overall this was a memorable trip for us and we hope it will be for you too. Thanks!

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$263

Bay and Beach Beauty

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 8 minutes

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$401

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

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$344

Oceanfront Oasis - Pinch me am I dreaming!!!

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 7 minutes

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$6,186

PALMS 309

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 5

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$86

82754 Overseas Highway

Islamorada house

5 bedrooms / 3 bathrooms / sleeps 10

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$982

Futura Yacht Club # 205

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 4

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$148

Islamorada Waterfront Paradise Getaway!

Islamorada house

1 bedroom / 1 bathroom / sleeps 2

“AMAZING!!!!!!!” Ewa and Peter were incredible hosts at this beautiful property. We felt right at home immediately and had so many activities to do plus Ewa and Peter had loads of great tips when we asked. The studio was so well stocked with all the essentials and then even the ones you forgot! It was wonderful to see a manatee swim up past the dock our first morning there. A very magical spot with generous hosts. It had everything we wanted and then some. After a week there and driving around the whole Keys it was 100% the most perfect choice for us. I miss those hammocks!

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$259

Executive Bay G-5

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

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$115

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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$667

LYONS LANDING

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 10

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$262

107 San Remo Drive

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 6

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$393

137 LeSerra Lane

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 6

“The best house we have rented in the keys!” This is the best house we have ever rented in the keys! The furnishings are modern, up-to-date and comfortable, the layout is perfect, the house is well-equipped and well-maintained, and the view is fabulous! Water on all sides, either the canal, ocean or bay, so no matter what room you are in you have a fantastic view! The location at MM 76.4 Is very convenient to everything in Islamorada including some great restaurants, and if you have a boat, you are only one house in from the ocean. I would definitely rent this house again!

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$368

Bay Harbour C-312

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 6

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$328

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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$574

102 Columbus Drive

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 4

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$126

141 Ocean Lane

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 6

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$210

Islamorada Waterfront Paradise 2

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

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$584

Paradise Beach Sandy Oceanfront

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 25 minutes

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$1,260

HOUSE DORADO

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

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$617

Windy Cove #3

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 6

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$328

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

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$792

Alligator Reef - Conch Home

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

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$733

Little Bay Cottage

Islamorada house

1 bedroom / 2 bathrooms / sleeps 6

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$492

50 Schooner Bay

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 8

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$1,064

Windy Cove #1

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 6

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$247

RIOLO VILLA

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

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$132

ANTIGUA PLACE

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 6

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$187

MANATEE MANOR

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

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$198

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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$382

Gorgeous waterfront home

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

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$460

WEST LAKE PLAZA

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 5

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$133

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

$1,260

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