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Vacation Rentals & House Rentals in Islamorada

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179 house rentals

Oceanfrontparadise: 209

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$285

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$1,720

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 57 minutes

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$164

Bay and Beach Beauty

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 8 minutes

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Price per night from

$401

NEW Interior Oceanfront 5th Floor End Unit, Pool, WiFi, Great Ocean Views!

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 31 minutes

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$206

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

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

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$344

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

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

WELCOME TO PARADISE! In the heart of Islamorada

Islamorada condo

1 bedroom / 1 bathroom / sleeps 5

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$168

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

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms / 3 bathrooms / sleeps 6

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$310

Islamorada Waterfront Paradise 2

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$585

Bayside Condo, marina, pool and beach

Islamorada condo

3 bedrooms / 2 bathrooms / sleeps 6

“The Best Keys Location” My family stayed at this lovely Futura Yacht Club Condo for three weeks this July. We have stayed at many other units in this complex over the years but this unit was one of the nicest we have seen. The unit has been remodeled and it has everything you would need for a great Keys vacation. Futura Yacht club has a big heated pool, tennis courts and if you are a boater a great marina with its own boat ramp which made it easy for us to enjoy our boat and jet ski's. It is a gated complex with security, centrally located to all the activities & restaurants in the area. We found the owner most helpful, accommodating and easy to deal with. We are looking forward to our next stay!!

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Price per night from

$222

Experience the Florida Keys like never before!!!

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 6

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$243

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

2 bedrooms / 3 bathrooms / sleeps 6

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$356

Bay Front Beauty/ Summer Sea Must See!!!!

Islamorada condo

1 bedroom / 1 bathroom / sleeps 4

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$158

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$792

Beautiful Captain's Cove

Islamorada villa

3 bedrooms / 2 bathrooms / sleeps 6

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$422

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

Gorgeous waterfront home

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$460

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

Manatee Bay

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$262

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$376

DEC & APRIL DEAL MONTH MINIMUM ENJOY! 9545791140

Islamorada apartment

3 bedrooms / 2 bathrooms / sleeps 8

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$172

2 Acres on the Atlantic Ocean in Islamorada, Florida

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 49 minutes

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$373

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

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

Newly Renovated Townhome In Tropical Paradise

Islamorada townhouse

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$133

Paradise Found - Sandy Beach, Beachside Bar, Great Views, And Dock

Islamorada villa

3 bedrooms / 3 bathrooms / sleeps 6

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$1,151

Islamorada cottage on deep water canal

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 29 minutes

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Price per night from

$170

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

Paradise at Islamorada

Islamorada townhouse

2 bedrooms / 2 bathrooms / sleeps 8

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$161

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

Lazy Daze Beach House 5 Star Modern Oceanfront Islamorada Townhome on the Beach!

Islamorada townhouse

2 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$333

Windley Key, FL Keys

Islamorada caravan/mobile home

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$130

Mile Marker 87 - Mina Bay - Oceanfront "Million Dollar View"

Islamorada townhouse

2 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$150

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rentals in Islamorada

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