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Islamorada Rentals with Pools

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161 house rentals in Islamorada with pools

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$1,720

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.

Match: Swimming pool

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Price per night from

$1,227

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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Price per night from

$164

Come relax in Islamorada, the tropical jewel of the Florida Keys!!

Islamorada apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 25 minutes

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Price per night from

$200

100 Palo De Oro Drive

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$430

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

Match: Swimming pool

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Price per night from

$206

PALMS 309

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 5

Match: Swimming pool

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Price per night from

$86

BEACON REEF 310

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$113

LYONS LANDING

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Swimming pool

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Price per night from

$263

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$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

Match: Swimming pool

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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

Match: Swimming pool

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Price per night from

$6,191

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!

Match: Swimming pool

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Price per night from

$229

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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Price per night from

$80

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$310

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

Match: Swimming pool

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Price per night from

$243

50 Schooner Bay

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$1,064

FLAMINGO COTTAGE

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$117

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

2 bedrooms / 3 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$356

PALMS 405

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$103

BEACON REEF 222

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Match: Swimming pool

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Price per night from

$134

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

Islamorada condo

1 bedroom / 1 bathroom / sleeps 4

Match: Swimming pool

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Price per night from

$158

HOUSE DORADO

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$618

"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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Price per night from

$422

Windy Cove #1

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$247

Paradise Beach Sandy Oceanfront

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 25 minutes

Match: Swimming pool

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Price per night from

$1,261

Windy Cove #3

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$328

PALMS 402

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$80

MANATEE MANOR

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$199

BEACON REEF 501

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$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.

Match: Swimming pool

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Price per night from

$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

Match: Swimming pool

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Price per night from

$1,261

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$376

DEC & APRIL DEAL MONTH MINIMUM ENJOY! 9545791140

Islamorada apartment

3 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$172

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

Match: Swimming pool

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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

Match: Swimming pool

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Price per night from

$382

Viewing 38 of 161
rentals in Islamorada

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