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Islamorada Vacation Rentals with Boat Dock

(58 rentals)
Islamorada Cottage
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

The Cottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on Florida Bay. The Cottage is a “conch-style” cottage which was just completely remodeled and renovated and is completely new, from the tile floors to the new tongue-and-groove...

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$290
avg per night
Islamorada Villa
Sleeps 4, 2 bedrooms, 2 bathrooms
14 reviews

Distance to beach: 5 miles to Anne's Beach

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Welcome to The Nest Villa & Marina in the heart of beautiful IslamoradaNestled on a picturesque 1-acre lot overlooking the stunning Florida Bay in the Florida Keys, the Nest Villa offers a perfect blend of privacy and proximity. This exclusive residence is one of seven privately owned villas,...

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Featured review

"Amazing location, view, and super clean!"

My 18 yr old son and I stayed here at the end of September and it was a fantastic trip!We have been going to the keys for 14 years several times a year. This unit is the cleanest we have ever seen!...

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$325
avg per night
Islamorada House
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

Key Amenities

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

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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Featured review

"Beautiful stay"

We had the best time at this house! Giovanna and her husband were wonderful hosts and were on top of everything we needed. The house itself is in a great location close to shops and restaurants. Book the...

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$1,101
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 2 bathrooms
7 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

Great house! Great location!HOUSE ON CANAL… 34 foot concrete dock with fish cleaning stand, water and electricity. Bring your boat, great boat ramps. The house is a short distance to supermarkets, movie theaters, dive shops, and full service marinas with fuel, bait and tackle. We are also...

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Featured review

"Excellent vacation rental"

This house is beautiful. Right on a canal where we kept our boat for the week. Manatees came by to visit daily. Caught keeper mangrove snapper right there. Neighbors were amazingly friendly. Everything...

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$297
avg per night
Islamorada House
Sleeps 8, 4 bedrooms, 3 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This beautiful, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. Situated in a beautiful upscale neighborhood of all waterfront homes, the house is equipped with all the comforts of home. It is extra clean and modernly furnished.Upstairs...

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Featured review

"Perfection in paradise!"

This was a perfect house! Easy and quick access to ocean and gulf, docked 35’ boat right at the house, large pool with hot tub, plenty of parking for vehicles and trailers, very clean, well stocked, tiki...

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$697
avg per night

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Islamorada House
Sleeps 10, 5 bedrooms, 7.5 bathrooms

Distance to beach: 4 miles to Founders

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool

About this property

Rare Summer Openings! Your Private Resort Awaits in IslamoradaIf you’ve been dreaming of an island escape with all the luxury of a high-end resort but none of the crowds, this is your chance.Your Own Private Resort in the Florida KeysFrom the moment you arrive, this estate feels more...

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Islamorada House
Sleeps 8, 3 bedrooms, 3.5 bathrooms
2 reviews

Key Amenities

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

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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Featured review

"Bayside Paradise Perfection"

Our family has been traveling to Islamorada for Spring Break for the last 4 years and this was by far our favorite place to stay! Our family enjoyed the private oasis that the townhome provided. We felt...

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$978
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 2 miles to Founders Park

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

*Discover Elevated Island Living at Sea Breeze 41 Luxury 3BR/2BA Condo with Private Boat Slip in Exclusive Coral Harbour Club, IslamoradaWelcome to Sea Breeze 41 — your personal slice of tropical paradise in the heart of the Florida Keys. Nestled within the highly coveted Coral Harbour Club,...

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$202
avg per night
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