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Vacation Rentals & House Rentals in Islamorada

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194 house rentals

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

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$1,720

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

BEACON REEF 310

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

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$113

LYONS LANDING

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 10

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$263

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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$667

WELCOME TO PARADISE! In the heart of Islamorada

Islamorada condo

1 bedroom / 1 bathroom / sleeps 5

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$168

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

BROCK HAUS ON THE GULF

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Absolutely Beautiful and convenient for boaters!” Our family stayed here for a week in late March. We had plenty of room and everything we needed was available. This is a gorgeous condo overlooking the Florida Bay. You get to see an awesome sunset every day. We also brought our boat and the dock is literally right across the condo and ocean access is not too far away by water. Manatees visited the dock about every day, you can see picture below. We looked at other condo options and by far this was the best that suited our needs. The service provided was excellent. They were a phone call away if we needed anything. We will definitely be staying here again. Thank you so much!

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$229

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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$575

PALMS 314

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Wow, what a beautiful view” This condo was clean, nicely furnished and had a view to die for. We really appreciated the washer and dryer in the unit, which most did not have. Also, being on the end we had "the window" in the master bedroom and in the daytime the view would take your breath. However, at night the lights from the parking lot would shine into our bedroom. Alas, with the flip of a switch an outside shutter would roll down and the room was completely dark. Talk about sleeping well! As for the complex, everyone was very friendly and we made some very good friends. The pool was heated and the hot tub was always warm and enjoyable. We have already made plans to go back next year. If you have the chance to rent a unit there, GO, you will not be sorry.

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$80

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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$585

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

LITTLE BAY - Cottage

Islamorada villa

2 bedrooms / 2 bathrooms / sleeps 6

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$430

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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$222

FLAMINGO COTTAGE

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

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$117

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

2 bedrooms / 3 bathrooms / sleeps 6

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$356

PALMS 405

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 6

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$103

BEACON REEF 222

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

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$134

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

Islamorada condo

1 bedroom / 1 bathroom / sleeps 4

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$158

HOUSE DORADO

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

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$618

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

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$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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$1,261

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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$430

ANTIGUA PLACE

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 6

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$188

PALMS 402

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

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$80

MANATEE MANOR

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

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$199

BEACON REEF 501

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

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$110

PALMS 417

Islamorada apartment

1 bedroom / 2 bathrooms / sleeps 2

“Paradise on the ocean” We rented Palm 417 for the month of March 2014. The condo has been very nicely updated and although not direct ocean front view; it does have partial view of the ocean side and a good view of the bay side with amazing sunsets. People in surrounding condos were very friendly; and one condo owner gave us some lovely smoked fish. Some road noise but we soon got used to it as the condo and location soon out weighted any small negative of the road noise. Holiday Keys Rentals agency went out of their way to assist us. And would definately rent one of their properties again; esp Palm 417.

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$70

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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$1,261

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

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$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

RIOLO VILLA

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

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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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$1,261

Viewing 38 of 194
rentals in Islamorada

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