Monthly Rentals in Islamorada

(62 rentals)
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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

This beautifully furnished waterfront home with ocean views will thrill the most ardent diver or fisherman and his family. You will love the luxury of a heated pool, magnificent view, and protected deep water dockage for multiple boats. It is located on a large harbor with multiple sailing yachts and ...

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Property Type

Islamorada House

"House and location was wounderful"

House was well maintained with all you could need. the location was perfect on the creek. we had a great stay and the management was very accommodating to all our needs.

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2 BR | 2 BA | Sleeps 4 | Quick View

$175

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Beautiful ocean front apartment with easy access to pool ,spa and beach. Dock with boat slips and tiki hut overlooking Atlantic Ocean. Community exercise room Master Bedroom overlooking the ocean Two bedrooms, two full baths. Gourmet equipped kitchen Laundry room Balcony with spiral stairs ...

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Property Type

Islamorada Apartment

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Welcome to our beautiful, private and secure gated community with all of the amenities to make your vacation as relaxing or exciting as you wish. Located on Plantation Key in Islamorada at mile marker 88.5 on the bay side and boasting a great 60 slip marina, it provides quick access to the ocean via Snake ...

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Property Type

Islamorada Condo

"Wonderful"

I highly recommend this vacation spot. Not only is the condo very nice the whole property is set up for your every need. The owner and property manager are very nice and accommodating. I was amazed by the ...

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2 BR | 2 BA | Sleeps 4 | Quick View

$222

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

SPECIAL 2024 SUMMER SALE RATES - ONLY JULY IS LEFT! July is the beginning of lobster season. Don't miss it. Beacon Reef Condo Oceanfront Islamorada, Florida (Max 4 Persons / **MONTHLY RENTALS ONLY!!) Come and enjoy our Paradise Found 2nd home. FREE BOAT DOCKAGE (with proof of insurance) In the ...

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Property Type

Islamorada Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Immerse yourself in the luxury and beauty of Oceanside, a brand-new gated community with 9 beachfront homes nestled in the heart of Islamorada. Our 4 bedroom home invites you to experience modern coastal comfort while its nearly 3000 square feet of indoor space provide ample room for family and friends. ...

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Property Type

Islamorada House

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront

About this property

Seeing is believing. The Captain's Quarters is a direct, oceanfront home on the Atlantic shoreline of Islamorada. For your planned getaway, come enjoy truly private and relaxing oceanfront living in the heart of Islamorada, in a unique home boasting a treasure-trove of Florida Keys history. The ...

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Property Type

Islamorada House

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2 BR | 1.5 BA | Sleeps 6 | Quick View

$97

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Beautiful area of island on ocean

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Property Type

Islamorada Condo

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3 BR | 3 BA | Sleeps 6 | Quick View

Distance to beach: 0.5 miles to White Marlin Beach

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

*******Check us out on VRBO No. 2003434******** Please go to ....**To our guests** Nautilus Getaway has always been proud to utilize a contact-less check in process. We use CDC recommended standards for disinfecting in our all our cleaning protocols.As soon as you walk into this home you will ...

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Property Type

Islamorada House

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3 BR | 2 BA | Sleeps 6 | Quick View

$217

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

The moment you step inside this calming retreat in exclusive Venetian Shores you feel on vacation with permanently assigned boat slip in private marina just around the corner. All new kitchen, baths, porcelain tile flooring, fully furniture and LOTS more. Three bedrooms, two bath home on a peaceful plugged ...

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Property Type

Islamorada House

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4 BR | 4.5 BA | Sleeps 8 | Quick View

$1140

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Nestled between the Cheeca Lodge and Caribbean Resort, our 4-bedroom oceanside home offers a unique beachfront experience for those looking for a luxurious and private getaway. Each spacious bedroom and en suite bathroom is inspired by modern coastal furnishings. Perfect for entertaining family and friends, ...

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Property Type

Islamorada House

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$1056

avg/night

View Details

Key Amenities

  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Private pool

About this property

Traditional coastal cottage styling built in 2017 and the Pool was added in 2020. Large backyard beach and only steps to the turquoise waters of the Atlantic Ocean. Kayak, paddle board, or kite ski from your backyard! Plenty of parking out front and private gated access; fencing around the perimeter. ...

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Property Type

Islamorada House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

PLEASE INQUIRE WITHIN FOR ALL STAYS AND SPECIAL DEALS!!!OCEANFRONT Jewel in the Heart of Islamorada and on Tavernier Creek allows for easy access to everything the Upper Keys have to offer and direct Ocean and Bay access. This Open Water home HAS IT ALL. -Brand New (Sept 2017) Huge, heated ...

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Property Type

Islamorada House

"Love this house"

Great location! Sunrises and sunsets were amazing. Easy location to open water, kids loved going out on boat. Fishing right off the dock. Lots of wildlife. Everyone loved the outdoor bathroom! Very convenient. ...

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Islamorada Vacation Rentals