Islamorada Vacation Rentals with Boat Dock

(64 rentals)
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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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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Founders Park

$149

avg/night

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Key Amenities

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

About this property

Experience high-end coastal luxury while staying at “Sea Breeze 41” in the highly sought-after Coral Harbour Club Condominium (CHC) . Your spacious 3 Bedroom / 2 Bathroom island getaway exudes luxury tropical vibes and is professionally decorated in Tropical Modern style. A 30' Boat Slip ...

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Property Type

Islamorada Condo

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Key Amenities

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

About this property

Islamorada waterfront gem located on Sandy Cove Basin with total renovations completed in 2024. New pool and spa, new deep water dock. Three en suite king bedrooms. Nicely appointed kitchen. Private gated and fenced yard with ample parking.

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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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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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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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5 BR | 3.5 BA | Sleeps 17 | Quick View

2

$2400

avg/night

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Key Amenities

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

About this property

Southern Diversion is located directly in the Village of Islamorada in the Florida Keys and walking distance to all the major restaurants and shopping. This is an exclusive oceanfront private gated estate home with 200 feet of oceanfront on two acres. This property also features 200 feet of dock, Boat ...

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Property Type

Islamorada Estate

"Milestones Birthday Celebration /Family Vacation"

Absolutely beautiful home..Featured everything we needed to enjoy our vacation..Spacious enough for 14 people. Close to places if we decided to go out n explore..Epic week.!!Thank you

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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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5 BR | 3 BA | Sleeps 12 | Quick View

4

$891

avg/night

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Key Amenities

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

About this property

Deam home in they keys is one of the very few legal weekly rentals in Islamorada. It is a 4000 square foot home on water with heated/chilled Pool. Located in an exclusive area of all waterfront homes. This immaculate two-story home offers a luxurious and very private setting. Ryan's place has 5 large ...

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Property Type

Islamorada House

"Amazing Family Vacation! Beautiful and affordable home in amazing location."

This was our first family trip to the FL keys and we had the most amazing time! Bridget was so helpful, especially since we booked prior to covid and decided to take our planned trip. She answered all my ...

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Key Amenities

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

About this property

Welcome to the coastal home of your dreams in the relaxed residential retreat of Coral Cove. As soon as you pull into our driveway, you’ll be able to walk, bike or paddle everywhere in town. Our newly constructed two-story house has 3 spacious bedrooms, a study area with bunk beds, plus 3 and ...

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Property Type

Islamorada House

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2 BR | 2.5 BA | Sleeps 6 | Quick View

2

$300

avg/night

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Key Amenities

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

About this property

2 Bed & 2.5 Bath Villa in Anglers Reef with Boat slip.Upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here: gorgeous private beach, heated resort style pool, private back yard patio with barbecue, front porch seating, upstairs balcony. Spacious ...

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Property Type

Islamorada Villa

"Great accomodations"

Beautifully decorated house in the Keys. Very spacious and comfortable. Kitchen was fully stocked. Plenty of linens and extra towels. The community dock has kayaks we used. There are lobsters under ...

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1 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 4 miles to Founders Park

$260

avg/night

View Details

Key Amenities

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

About this property

Bayside is a first floor apartment overlooking the water. Bayside is located on a small resort property nestled in a native hammock on Florida Bay. An easy 90 minute drive from Miami International Airport, this property is located in the heart of Islamorada, directly on Florida Bay. Bayside is fully air ...

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Property Type

Islamorada Condo

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Key Amenities

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

About this property

Breathtaking Waterfront 2/2.5 Townhouse In Desirable Futura Yacht Club. Lots of outdoor living space,great for entertaining and enjoying the magnificent unobstructed Bayviews and beautiful sunset! Futuravis a gated community with a large pool tennis courts, boat ramp,beach and boat/trailer storage,parking ...

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Property Type

Islamorada Townhome

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Key Amenities

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

About this property

SPECIAL SUMMER SALE RATES MAY-JULY!! SEE SPECIAL POSTED RATES MAY-JULY! 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 fishing capital of the world, Islamorada. ...

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Property Type

Islamorada Condo

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Islamorada Vacation Rentals