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Islamorada Rentals with Hot Tubs

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106 house rentals in Islamorada with hot tubs

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

Islamorada Luxury Waterfront Condo with Boat Slip

Islamorada apartment

2 bedrooms / 3 bathrooms / sleeps 6

“Beautifully appointed, waterside condo!” This property is a beautiful, two bedroom condo, very well appointed, with everything we needed for a great stay! Islamorada is a great middle point to see the other parts of the Keys, and close to great restaurants. The porch offers lovely sunrises, and peaceful enjoyment of the waterway view and harbor. The pool is heated and quiet. The owners were very helpful with our questions. We would definitely stay at this property again, and recommend it to others!

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Price per night from

$225

100 Palo De Oro Drive

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

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$430

Incredible Luxury Home with Waterfront!! Paradise

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 2 hours 39 minutes

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Price per night from

$1,432

BEACON REEF 310

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

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$113

PALMS 309

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 5

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$86

THE PERFECT GETAWAY

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 10

“The owner was understanding and worked with us” I was scheduled to rent from Dec 29th to Jan 4th and expected 7 friends to join me. For multiple personal reasons four of the seven had to back out and it is not the place you want to be without the full group. I was very concerned and as soon as I knew there would only be three of us I contacted the owner and explained what had happened and asked if I could reschedule. He immediately responded that he would be willing to reschedule. Not only have I told my guests, but several friends who frequently rent in the Hilton Head/ Daufuskie area how accommodating this owner has been. We are looking forward to our visit there.

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$472

82754 Overseas Highway

Islamorada house

5 bedrooms / 3 bathrooms / sleeps 10

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$883

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

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 35 minutes

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Price per night from

$590

Beautiful Captain's Cove

Islamorada villa

3 bedrooms / 2 bathrooms / sleeps 6

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$384

Paradise Beach Sandy Oceanfront

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 12 minutes

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Price per night from

$935

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 49 minutes

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Price per night from

$317

THE PALMS 405 - 93

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 6

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$120

BEACON REEF 222

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

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$147

PALMS 402

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

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$80

BEACON REEF 501

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

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$110

Fabulous 2 level home - 3/2 each Level - Waterfront Pool Home in Islamorada!

Islamorada house

3 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 40 minutes

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Price per night from

$310

PALMS 417

Islamorada apartment

1 bedroom / 2 bathrooms / sleeps 4

“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

Elegant Bay Harbour Condo with 50 Foot Boat Slip

Islamorada apartment

3 bedrooms / 3 bathrooms / sleeps 6

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$501

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 12 minutes

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Price per night from

$1,102

PALMS 407

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

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$80

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

Islamorada villa

3 bedrooms / 3 bathrooms / sleeps 6

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$413

PALMS 404

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 6

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$77

129 Venetian Drive

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

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$249

Oceanfront Islamorada Condo with Huge T-Dock

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

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$157

PALMS 301

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 6

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$77

AZALEA WARTERFRONT

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 6

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$177

PALMS 317

Islamorada apartment

1 bedroom / 2 bathrooms / sleeps 4

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$63

BEACON REEF 306

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

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$100

Islamorada cottage on deep water canal

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

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$177

Oceanfront 2/2 Condo in Beacon Reef - Free boat dock

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

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$236

3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.

Islamorada apartment

3 bedrooms / 2 bathrooms / sleeps 6

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$279

Great rentals within 20 miles that match your search

Paradise on the water

Key Largo house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 1 hour 17 minutes

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Price per night from

$294

Good Times and Tan Lines - (New Listing) Deluxe Renovated Ocean View 2B/2B Condo

Tavernier condo

2 bedrooms / 2 bathrooms / sleeps 6

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$252

Clean Keys 3/3 w/Davits Clear Canal Bay Side/Views Fenced 2Level Tavernier Home

Tavernier house

3 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 3 hours 12 minutes

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Price per night from

$177

Penthouse Paradise | Developer Unit w/ Every ★ Upgrade Possible!!

Layton apartment

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 20 minutes

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Price per night from

$883

LISENCED MGR! BRAND NEW & TOTALLY RENOVATED 2/2 SUITE! OCEANFRONT BEACH RESORT!

Key Largo apartment

2 bedrooms / 2 bathrooms / sleeps 6

“A great location for accomplishing our interests while visiting” This rental was a perfect set up for two people - also very clean, convenient and seeing the egret's nest outside the patio was special. The beach chairs in the closet need attention as it was nice to have Harry Harris park near by. Thank you.

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Price per night from

$236

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