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Islamorada Vacation Rentals with Boat Dock

(58 rentals)
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 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
Islamorada Townhome
Sleeps 4, 2 bedrooms, 2.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • 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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Featured review

"Great Location"

This condo was very conveniently located. We could snorkel at John Pennekamp and kayak the mangroves of Islamorado. Plenty of close good seafood restaurants in vicinity. Spend the day at Bahia Honda.

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$283
avg per night
Islamorada Condo
Sleeps 4, 1 bedroom, 2 bathrooms

Distance to beach: 4 miles to Founders Park

Key Amenities

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

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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$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

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Islamorada House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

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

About this property

Ocean side pool home with private dock. Beautifully decorated with 2 bedrooms and 2 bathrooms on the main level. Master bedroom has a queen size bed and a full bath. The second bedroom has twin beds. Downstairs is a suite with sleeping accommodations for 4 people and full bathroom. Linens and towels...

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$328
avg per night
Islamorada Apartment
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

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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$183
avg per night
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
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