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Islamorada Vacation Rentals with Boat Dock

(58 rentals)
Islamorada House
Sleeps 10, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • WiFi

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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$667
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 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 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 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

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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 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 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
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